CN106946868A - Nitric oxide donator type coumarin derivative, its preparation method and medical usage - Google Patents

Nitric oxide donator type coumarin derivative, its preparation method and medical usage Download PDF

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CN106946868A
CN106946868A CN201611175141.2A CN201611175141A CN106946868A CN 106946868 A CN106946868 A CN 106946868A CN 201611175141 A CN201611175141 A CN 201611175141A CN 106946868 A CN106946868 A CN 106946868A
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carboxylic acid
furazan
propoxycoumarin
piperazinyl
butoxycoumarin
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CN106946868B (en
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何黎琴
张灼
王蓉
柏志伟
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Li Duankai
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Abstract

本发明涉及药物化学和药物治疗学领域，具体涉及一氧化氮供体型香豆素衍生物及其制备方法和在制药中的应用。该类化合物具有抗肿瘤作用，可用于制备抗肿瘤药物。The invention relates to the fields of medicinal chemistry and pharmacotherapeutics, in particular to a nitric oxide donor type coumarin derivative, a preparation method thereof and an application in pharmacy. The compounds have antitumor effects and can be used for preparing antitumor drugs.

Description

一氧化氮供体型香豆素衍生物、其制备方法及医药用途Nitric oxide donating type coumarin derivative, its preparation method and medical use

技术领域technical field

本发明涉及药物化学和药物治疗学领域，具体涉及一类一氧化氮(NO)供体型香豆素衍生物或其药学上可接受的盐，它们的制备方法及医药用途，特别是在制备抗肿瘤药物中的应用。The present invention relates to the fields of medicinal chemistry and pharmacotherapeutics, in particular to a class of nitric oxide (NO) donor type coumarin derivatives or pharmaceutically acceptable salts thereof, their preparation methods and medical applications, especially in the preparation of anti- Application in tumor medicine.

背景技术Background technique

恶性肿瘤是当前危害人类健康的主要杀手之一。临床上用于治疗恶性肿瘤的药物有多种，但由于其存在的毒副作用，耐药性及低选择性等不足，使得多数肿瘤患者缺乏有效治疗。因此，寻找药效高、毒副作用小的新型抗肿瘤药物任重道远。Malignant tumors are one of the main killers that endanger human health. There are many kinds of drugs used to treat malignant tumors clinically, but due to their toxic side effects, drug resistance and low selectivity, most cancer patients lack effective treatment. Therefore, there is a long way to go to find new anti-tumor drugs with high efficacy and low side effects.

天然产物长期以来被认为是有效治疗药物的重要来源。从天然产物中寻找新药或先导化合物的研究是当前国内外创制新药的重要研究方向和非常活跃的研究领域。除了从天然产物直接研究开发成有效的治疗新药物外，天然产物还是新药开发所依赖的新先导化合物取之不尽的源泉。以天然产物为先导化合物，结合结构与生物活性关系研究进一步进行结构修饰和类似物合成，以提高药效和降低毒性，已经成为新药创制的重要途径，而且已经取得了丰硕的成果。香豆素类化合物广泛存在于自然界中，具有抗菌、抗凝、抗氧化、抗炎和抗肿瘤等多种生理活性；其分子结构独特，具有良好的热力学和光化学稳定性，易于进行结构修饰并能方便地引入各种功能基团，一直受到国内外学者的广泛关注。近年来的研究表明，一些天然的香豆素类化合物能够选择性作用于肿瘤细胞，而对正常细胞毒性低，如七叶内酯，瑞香素、东莨菪素、新生霉素等(Natl.Cancer Inst.2000,92,242-248；BiochemPharmacoll,2004, 67(9):1778-1779)，为研发高效低毒的抗肿瘤药物提供了良好的前景。由于天然香豆素类化合物存在抗肿瘤活性不够强、水溶性较差或体内代谢不稳定、生物利用度低等缺陷，使其临床应用受到限制。因此，运用药物研发的一些理念和手段对其进行结构修饰、改造及构效关系研究成为药物化学领域研究的热点。研究发现，大多数具有抗肿瘤作用的香豆素类化合物在C7 位有羟基，C3位有取代基，一些具有高生物活性或具有临床治疗作用的7-羟基和C3位香豆素结构修饰及改造物已见报道(Eur J Med Chem 2013,68:103-110；Bioorg Med Chem,2013, 21:7107-7117)，这为香豆素类化合物在抗肿瘤领域的开发和利用提供了一定的理论依据。Natural products have long been recognized as an important source of effective therapeutic drugs. Searching for new drugs or lead compounds from natural products is an important research direction and a very active research field for creating new drugs at home and abroad. In addition to the direct research and development of effective new drugs from natural products, natural products are also an inexhaustible source of new lead compounds on which new drug development depends. Taking natural products as lead compounds, combined with the study of the relationship between structure and biological activity, further structural modification and analog synthesis to improve drug efficacy and reduce toxicity has become an important way to create new drugs, and has achieved fruitful results. Coumarin compounds widely exist in nature and have various physiological activities such as antibacterial, anticoagulation, antioxidation, anti-inflammation and anti-tumor; their unique molecular structure has good thermodynamic and photochemical stability, and it is easy to carry out structural modification and It can easily introduce various functional groups, and has been widely concerned by scholars at home and abroad. Studies in recent years have shown that some natural coumarin compounds can selectively act on tumor cells, and have low toxicity to normal cells, such as escin, daphnetin, scopolamine, novobiocin, etc. (Natl.Cancer Inst.2000, 92, 242-248; BiochemPharmacoll, 2004, 67(9): 1778-1779), which provides a good prospect for the development of anti-tumor drugs with high efficiency and low toxicity. Due to the shortcomings of natural coumarin compounds such as insufficient antitumor activity, poor water solubility, unstable metabolism in vivo, and low bioavailability, their clinical application is limited. Therefore, using some concepts and methods of drug development to carry out structural modification, transformation and structure-activity relationship research has become a research hotspot in the field of medicinal chemistry. Studies have found that most coumarin compounds with anti-tumor effects have a hydroxyl group at the C7 position and a substituent at the C3 position, and some 7-hydroxyl and C3-position coumarin structural modifications and Transformations have been reported (Eur J Med Chem 2013,68:103-110; Bioorg Med Chem,2013, 21:7107-7117), which provides a certain basis for the development and utilization of coumarin compounds in the field of anti-tumor Theoretical basis.

NO是体内重要的效应分子，参与许多重要的生理过程。研究发现，高浓度的NO可诱导肿瘤细胞凋亡，阻止肿瘤的扩散和转移(J Med Chem,2008,51(15):4834-4838)。研究也表明，将具有一定抗肿瘤活性的化合物与呋咱氮氧化物偶联，得到的偶联物可发挥协同效应，增强抗肿瘤效果(J Med Chem,2014,57:9343-9356)。本发明在香豆素3-位通过连接桥与具有抗肿瘤作用的NO供体相结合，设计、合成了Ⅰ类NO供体型香豆素衍生物。考虑到药物具有适合的脂水分配系数才能被充分吸收，达到较好的生物利用度，而胺基是药物中最常见的基团，在药物分子中引入胺类结构可以提高其水溶性，且常利于化合物通过氢键与生物靶标结合，在其7-位引入氨基片段，以增加其水溶性，提高其生物利用度，设计、合成了Ⅱ类NO供体型香豆素衍生物。NO is an important effector molecule in the body and participates in many important physiological processes. Studies have found that high concentrations of NO can induce tumor cell apoptosis and prevent tumor spread and metastasis (J Med Chem, 2008, 51(15):4834-4838). Studies have also shown that by coupling a compound with certain antitumor activity to furazan nitrogen oxide, the resulting conjugate can exert a synergistic effect and enhance the antitumor effect (J Med Chem, 2014, 57:9343-9356). The present invention combines the 3-position of coumarin with the NO donor with anti-tumor effect through a connecting bridge, and designs and synthesizes class I NO donor type coumarin derivatives. Considering that the drug has a suitable lipid-water partition coefficient to be fully absorbed and achieve better bioavailability, and the amine group is the most common group in the drug, the introduction of an amine structure into the drug molecule can improve its water solubility, and It is often beneficial for compounds to combine with biological targets through hydrogen bonds, and amino fragments are introduced at the 7-position to increase their water solubility and bioavailability. Class II NO-donating coumarin derivatives were designed and synthesized.

发明内容Contents of the invention

本发明首次公开了一类具有抗肿瘤活性的呋咱氮氧化物类NO供体型的香豆素衍生物或其药学上可接受的盐，它们的制备方法及医药用途，特别是在制备抗肿瘤药物中的应用。药理实验结果表明，该类化合物具有良好的抗肿瘤活性，因此，该类化合物可能适用于治疗临床上多种恶性肿瘤。The invention discloses for the first time a class of furazan nitrogen oxide NO donor coumarin derivatives or pharmaceutically acceptable salts thereof with anti-tumor activity, their preparation method and medical application, especially in the preparation of anti-tumor application in medicine. The results of pharmacological experiments show that this type of compound has good antitumor activity, therefore, this type of compound may be suitable for treating various malignant tumors in clinic.

本发明公开的新化合物是通式I、Ⅱ所示的NO供体型香豆素衍生物及其药学上可接受的盐：The new compound disclosed by the present invention is the NO-donating coumarin derivatives shown in the general formulas I and II and pharmaceutically acceptable salts thereof:

通式I中：X代表-O-或-NH-；R代表-(CH2)n-，其中n＝1～6，-CH(CH3)CH2-， -CH(CH3)(CH2)2-，-(CH2)2O(CH2)2-，-Ph(CH2)2-，-(CH2)2NH(CH2)2-，-CH2CH＝CHCH2-或 -CH2C≡CCH2-；In general formula I: X represents -O- or -NH-; R represents -(CH 2 )n-, where n=1~6, -CH(CH 3 )CH 2 -, -CH(CH 3 )(CH 2 ) 2 -, -(CH 2 ) 2 O(CH 2 ) 2 -, -Ph(CH 2 ) 2 -, -(CH 2 ) 2 NH(CH 2 ) 2 -, -CH 2 CH=CHCH 2 - or -CH 2 C≡CCH 2 -;

通式Ⅱ中：n＝1～6，X代表-O-或-NH-；R代表-(CH2)n-，其中n＝1～6，-CH(CH3)CH2-， -CH(CH3)(CH2)2-，-(CH2)2O(CH2)2-，-Ph(CH2)2-，-(CH2)2NH(CH2)2-，-CH2CH＝CHCH2-或-CH2C≡CCH2-；R1代表NR1R2；R1和R2可相同或不同，并且彼此独立地代表氢原子、C1-C6烷基、苯基、苄基、苯乙基或R1和R2与其所连接的氮原子一起形成五至七元脂肪杂环或芳杂环，该环基可任意地由下述相同或不同的取代基单取代至五取代，所述取代基包括：C1-C6烷基、C1-C6烷氧基、羟基或羟基-(C1-C6)烷基。In general formula II: n=1~6, X stands for -O- or -NH-; R stands for -(CH 2 )n-, where n=1~6, -CH(CH 3 )CH 2 -, -CH (CH 3 )(CH 2 ) 2 -, -(CH 2 ) 2 O(CH 2 ) 2 -, -Ph(CH 2 ) 2 -, -(CH 2 ) 2 NH(CH 2 ) 2 -, -CH 2 CH=CHCH 2 -or -CH 2 C≡CCH 2 -; R 1 represents NR 1 R 2 ; R 1 and R 2 may be the same or different, and independently represent a hydrogen atom, C 1 -C 6 alkyl, Phenyl, benzyl, phenethyl or R 1 and R 2 form five to seven membered aliphatic heterocycles or aromatic heterocycles together with the nitrogen atom to which they are attached, and this ring group can be arbitrarily replaced by the following identical or different substituents Monosubstituted to pentasubstituted, the substituents include: C 1 -C 6 alkyl, C 1 -C 6 alkoxy, hydroxyl or hydroxy-(C 1 -C 6 )alkyl.

本发明优选的化合物为通式I所示的NO供体型香豆素衍生物：The preferred compound of the present invention is the NO donor type coumarin derivative shown in general formula I:

X代表-O-或-NH-；R代表-(CH2)n-，其中n＝2～6，-CH(CH3)CH2-，-CH(CH3)(CH2)2-，-(CH2)2O(CH2)2-，-Ph(CH2)2-，-CH2CH＝CHCH2-或-CH2C≡CCH2-；X stands for -O- or -NH-; R stands for -(CH 2 )n-, where n=2~6, -CH(CH 3 )CH 2 -, -CH(CH 3 )(CH 2 ) 2 -, -(CH 2 ) 2 O(CH 2 ) 2 -, -Ph(CH 2 ) 2 -, -CH 2 CH=CHCH 2 - or -CH 2 C≡CCH 2 -;

本发明优选的化合物为通式Ⅱ所示的NO供体型香豆素衍生物及其药学上可接受的盐：The preferred compounds of the present invention are NO-donating coumarin derivatives represented by general formula II and pharmaceutically acceptable salts thereof:

n＝2～6；X代表-O-或-NH-；R代表-(CH2)n-，其中n＝2～6，-CH(CH3)CH2-， -CH(CH3)(CH2)2-，-(CH2)2O(CH2)2-，-Ph(CH2)2-，-CH2CH＝CHCH2-或-CH2C≡CCH2-；R1代表氨基、二甲胺基、二乙胺基、二丙胺基、二正丁胺基、苯胺基、苄胺基、苯乙胺基、吡咯基、哌啶基、吗啡啉基、咪唑基、哌嗪基、4-甲基哌啶基、N-甲基哌嗪基、N-乙基哌嗪基或4-羟乙基哌嗪基。n=2～6; X represents -O- or -NH-; R represents -(CH 2 )n-, wherein n=2～6, -CH(CH 3 )CH 2 -, -CH(CH 3 )( CH 2 ) 2 -, -(CH 2 ) 2 O(CH 2 ) 2 -, -Ph(CH 2 ) 2 -, -CH 2 CH=CHCH 2 - or -CH 2 C≡CCH 2 -; R 1 represents Amino, dimethylamino, diethylamino, dipropylamino, di-n-butylamino, anilino, benzylamino, phenethylamino, pyrrolyl, piperidinyl, morpholinyl, imidazolyl, piperazine , 4-methylpiperidinyl, N-methylpiperazinyl, N-ethylpiperazinyl or 4-hydroxyethylpiperazinyl.

本发明进一步优选的化合物为通式I中所示的一氧化氮供体型香豆素衍生物：Further preferred compounds of the present invention are nitric oxide donating coumarin derivatives shown in general formula I:

X代表-O-或-NH-；R代表-(CH2)n-，其中n＝2～6，-CH(CH3)CH2-，-CH(CH3)(CH2)2-，-(CH2)2O(CH2)2-，-Ph(CH2)2-或-CH2C≡CCH2-；X stands for -O- or -NH-; R stands for -(CH 2 )n-, where n=2~6, -CH(CH 3 )CH 2 -, -CH(CH 3 )(CH 2 ) 2 -, -(CH 2 ) 2 O(CH 2 ) 2 -, -Ph(CH 2 ) 2 - or -CH 2 C≡CCH 2 -;

本发明进一步优选的化合物为通式Ⅱ中所示的NO供体型香豆素衍生物及其医学上可接受的盐：Further preferred compounds of the present invention are NO-donating coumarin derivatives shown in general formula II and pharmaceutically acceptable salts thereof:

n＝2～4；X代表-O-或-NH-；R代表-(CH2)n-，其中n＝2～6，-CH(CH3)CH2-，-CH(CH3)(CH2)2-， -(CH2)2O(CH2)2-，-Ph(CH2)2-或-CH2C≡CCH2-；R1代表氨基、二甲胺基、二乙胺基、苯胺基、苄胺基、苯乙胺基、哌啶基、吗啡啉基、哌嗪基、N-甲基哌嗪基、N-乙基哌嗪基或4-羟乙基哌嗪基。n=2～4; X represents -O- or -NH-; R represents -(CH 2 )n-, wherein n=2～6, -CH(CH 3 )CH 2 -, -CH(CH 3 )( CH 2 ) 2 -, -(CH 2 ) 2 O(CH 2 ) 2 -, -Ph(CH 2 ) 2 - or -CH 2 C≡CCH 2 -; R 1 represents amino, dimethylamino, diethyl Amine, anilino, benzylamino, phenethylamino, piperidinyl, morpholinyl, piperazinyl, N-methylpiperazinyl, N-ethylpiperazinyl or 4-hydroxyethylpiperazine base.

具体来说，通式I、Ⅱ中所示的香豆素衍生物优选自下列化合物：Specifically, the coumarin derivatives shown in general formula I and II are preferably selected from the following compounds:

香豆素-3-羧酸-1,2-乙二醇呋咱；Coumarin-3-carboxylic acid-1,2-ethylene glycol furazan;

香豆素-3-羧酸-1,2-丙二醇呋咱；Coumarin-3-carboxylate-1,2-propanediol furazan;

香豆素-3-羧酸-1,3-丙二醇呋咱；Coumarin-3-carboxylate-1,3-propanediol furazan;

香豆素-3-羧酸-1,3-丁二醇呋咱；Coumarin-3-carboxylic acid-1,3-butanediol furazan;

香豆素-3-羧酸-1,4-丁二醇呋咱；Coumarin-3-carboxylic acid-1,4-butanediol furazan;

香豆素-3-羧酸一缩乙二醇呋咱；Coumarin-3-carboxylic acid ethylene glycol furazan;

香豆素-3-羧酸-1,4-丁炔二醇呋咱；Coumarin-3-carboxylic acid-1,4-butynediol furazan;

香豆素-3-羧酸对羟基苯乙醇呋咱；Coumarin-3-carboxylate p-hydroxyphenylethylfurazan;

香豆素-3-羧氨基乙醇呋咱；Coumarin-3-carboxyaminoethanolfurazan;

香豆素-3-羧酸氨基丙醇呋咱；Coumarin-3-carboxylate aminopropanol furazan;

香豆素-3-羧酸异丙醇胺呋咱；Coumarin-3-carboxylate isopropanolamide furazan;

7-(2-氨基)乙氧基香豆素-3-羧酸1,2-乙二醇呋咱7-(2-Amino)ethoxycoumarin-3-carboxylic acid 1,2-ethylene glycol furazan

7-(2-二甲氨基)乙氧基香豆素-3-羧酸1,2-乙二醇呋咱；7-(2-Dimethylamino)ethoxycoumarin-3-carboxylic acid 1,2-ethylene glycol furazan;

7-(2-二乙氨基)乙氧基香豆素-3-羧酸1,2-乙二醇呋咱；7-(2-Diethylamino)ethoxycoumarin-3-carboxylic acid 1,2-ethylene glycol furazan;

7-(2-苯氨基)乙氧基香豆素-3-羧酸1,2-乙二醇呋咱；7-(2-phenylamino)ethoxycoumarin-3-carboxylic acid 1,2-ethylene glycol furazan;

7-(2-苄氨基)乙氧基香豆素-3-羧酸1,2-乙二醇呋咱；7-(2-Benzylamino)ethoxycoumarin-3-carboxylic acid 1,2-ethylene glycol furazan;

7-(2-苯乙氨基)乙氧基香豆素-3-羧酸1,2-乙二醇呋咱；7-(2-Phenylethylamino)ethoxycoumarin-3-carboxylic acid 1,2-ethylene glycol furazan;

7-[2-(1-哌啶基)]乙氧基香豆素-3-羧酸1,2-乙二醇呋咱；7-[2-(1-piperidinyl)]ethoxycoumarin-3-carboxylic acid 1,2-ethylene glycol furazan;

7-[2-(1-吗啡啉基)]乙氧基香豆素-3-羧酸1,2-乙二醇呋咱；7-[2-(1-morpholinyl)]ethoxycoumarin-3-carboxylic acid 1,2-ethylene glycol furazan;

7-[2-(1-哌嗪基)]乙氧基香豆素-3-羧酸1,2-乙二醇呋咱；7-[2-(1-piperazinyl)]ethoxycoumarin-3-carboxylic acid 1,2-ethylene glycol furazan;

7-[2-(4-甲基-1-哌嗪基)]乙氧基香豆素-3-羧酸1,2-乙二醇呋咱；7-[2-(4-Methyl-1-piperazinyl)]ethoxycoumarin-3-carboxylic acid 1,2-ethylene glycol furazan;

7-[2-(4-乙基-1-哌嗪基)]乙氧基香豆素-3-羧酸1,2-乙二醇呋咱；7-[2-(4-Ethyl-1-piperazinyl)]ethoxycoumarin-3-carboxylic acid 1,2-ethylene glycol furazan;

7-[2-(4-羟乙基-1-哌嗪基)]乙氧基香豆素-3-羧酸1,2-乙二醇呋咱；7-[2-(4-Hydroxyethyl-1-piperazinyl)]ethoxycoumarin-3-carboxylic acid 1,2-ethylene glycol furazan;

7-(2-氨基)乙氧基香豆素-3-羧酸1,2-丙二醇呋咱；7-(2-Amino)ethoxycoumarin-3-carboxylic acid 1,2-propanediol furazan;

7-(2-二甲氨基)乙氧基香豆素-3-羧酸1,2-丙二醇呋咱；7-(2-Dimethylamino)ethoxycoumarin-3-carboxylic acid 1,2-propanediol furazan;

7-(2-二乙氨基)乙氧基香豆素-3-羧酸1,2-丙二醇呋咱；7-(2-Diethylamino)ethoxycoumarin-3-carboxylic acid 1,2-propanediol furazan;

7-(2-苯氨基)乙氧基香豆素-3-羧酸1,2-丙二醇呋咱；7-(2-phenylamino)ethoxycoumarin-3-carboxylic acid 1,2-propanediol furazan;

7-(2-苄氨基)乙氧基香豆素-3-羧酸1,2-丙二醇呋咱；7-(2-Benzylamino)ethoxycoumarin-3-carboxylic acid 1,2-propanediol furazan;

7-(2-苯乙氨基)乙氧基香豆素-3-羧酸1,2-丙二醇呋咱；7-(2-Phenylethylamino)ethoxycoumarin-3-carboxylic acid 1,2-propanediol furazan;

7-[2-(1-哌啶基)]乙氧基香豆素-3-羧酸1,2-丙二醇呋咱；7-[2-(1-piperidinyl)]ethoxycoumarin-3-carboxylic acid 1,2-propanediol furazan;

7-[2-(1-吗啡啉基)]乙氧基香豆素-3-羧酸1,2-丙二醇呋咱；7-[2-(1-morpholinyl)]ethoxycoumarin-3-carboxylic acid 1,2-propanediol furazan;

7-[2-(1-哌嗪基)]乙氧基香豆素-3-羧酸1,2-丙二醇呋咱；7-[2-(1-piperazinyl)]ethoxycoumarin-3-carboxylic acid 1,2-propanediol furazan;

7-[2-(4-甲基-1-哌嗪基)]乙氧基香豆素-3-羧酸1,2-丙二醇呋咱；7-[2-(4-Methyl-1-piperazinyl)]ethoxycoumarin-3-carboxylic acid 1,2-propanediolfurazan;

7-[2-(4-乙基-1-哌嗪基)]乙氧基香豆素-3-羧酸1,2-丙二醇呋咱；7-[2-(4-Ethyl-1-piperazinyl)]ethoxycoumarin-3-carboxylic acid 1,2-propanediol furazan;

7-[2-(4-羟乙基-1-哌嗪基)]乙氧基香豆素-3-羧酸1,2-丙二醇呋咱；7-[2-(4-Hydroxyethyl-1-piperazinyl)]ethoxycoumarin-3-carboxylic acid 1,2-propanediol furazan;

7-(2-氨基)乙氧基香豆素-3-羧酸1,3-丙二醇呋咱；7-(2-Amino)ethoxycoumarin-3-carboxylic acid 1,3-propanediol furazan;

7-(2-二甲氨基)乙氧基香豆素-3-羧酸1,3-丙二醇呋咱；7-(2-Dimethylamino)ethoxycoumarin-3-carboxylic acid 1,3-propanediol furazan;

7-(2-二乙氨基)乙氧基香豆素-3-羧酸1,3-丙二醇呋咱；7-(2-Diethylamino)ethoxycoumarin-3-carboxylic acid 1,3-propanediol furazan;

7-(2-苯氨基)乙氧基香豆素-3-羧酸1,3-丙二醇呋咱；7-(2-phenylamino)ethoxycoumarin-3-carboxylic acid 1,3-propanediol furazan;

7-(2-苄氨基)乙氧基香豆素-3-羧酸1,3-丙二醇呋咱；7-(2-Benzylamino)ethoxycoumarin-3-carboxylic acid 1,3-propanediol furazan;

7-(2-苯乙氨基)乙氧基香豆素-3-羧酸1,3-丙二醇呋咱；7-(2-Phenylethylamino)ethoxycoumarin-3-carboxylic acid 1,3-propanediol furazan;

7-[2-(1-哌啶基)]乙氧基香豆素-3-羧酸1,3-丙二醇呋咱；7-[2-(1-piperidinyl)]ethoxycoumarin-3-carboxylic acid 1,3-propanediol furazan;

7-[2-(1-吗啡啉基)]乙氧基香豆素-3-羧酸1,3-丙二醇呋咱；7-[2-(1-morpholinyl)]ethoxycoumarin-3-carboxylic acid 1,3-propanediol furazan;

7-[2-(1-哌嗪基)]乙氧基香豆素-3-羧酸1,3-丙二醇呋咱；7-[2-(1-piperazinyl)]ethoxycoumarin-3-carboxylic acid 1,3-propanediol furazan;

7-[2-(4-甲基-1-哌嗪基)]乙氧基香豆素-3-羧酸1,3-丙二醇呋咱；7-[2-(4-Methyl-1-piperazinyl)]ethoxycoumarin-3-carboxylic acid 1,3-propanediolfurazan;

7-[2-(4-乙基-1-哌嗪基)]乙氧基香豆素-3-羧酸1,3-丙二醇呋咱；7-[2-(4-Ethyl-1-piperazinyl)]ethoxycoumarin-3-carboxylic acid 1,3-propanediol furazan;

7-[2-(4-羟乙基-1-哌嗪基)]乙氧基香豆素-3-羧酸1,3-丙二醇呋咱；7-[2-(4-Hydroxyethyl-1-piperazinyl)]ethoxycoumarin-3-carboxylic acid 1,3-propanediol furazan;

7-(2-氨基)乙氧基香豆素-3-羧酸1,3-丁二醇呋咱；7-(2-Amino)ethoxycoumarin-3-carboxylic acid 1,3-butanediol furazan;

7-(2-二甲氨基)乙氧基香豆素-3-羧酸1,3-丁二醇呋咱；7-(2-Dimethylamino)ethoxycoumarin-3-carboxylic acid 1,3-butanediol furazan;

7-(2-二乙氨基)乙氧基香豆素-3-羧酸1,3-丁二醇呋咱；7-(2-Diethylamino)ethoxycoumarin-3-carboxylic acid 1,3-butanediol furazan;

7-(2-苯氨基)乙氧基香豆素-3-羧酸1,3-丁二醇呋咱；7-(2-phenylamino)ethoxycoumarin-3-carboxylic acid 1,3-butanediol furazan;

7-(2-苄氨基)乙氧基香豆素-3-羧酸1,3-丁二醇呋咱；7-(2-Benzylamino)ethoxycoumarin-3-carboxylic acid 1,3-butanediol furazan;

7-(2-苯乙氨基)乙氧基香豆素-3-羧酸1,3-丁二醇呋咱；7-(2-Phenylethylamino)ethoxycoumarin-3-carboxylic acid 1,3-butanediol furazan;

7-[2-(1-哌啶基)]乙氧基香豆素-3-羧酸1,3-丁二醇呋咱；7-[2-(1-piperidinyl)]ethoxycoumarin-3-carboxylic acid 1,3-butanediolfurazan;

7-[2-(1-吗啡啉基)]乙氧基香豆素-3-羧酸1,3-丁二醇呋咱；7-[2-(1-morpholinyl)]ethoxycoumarin-3-carboxylic acid 1,3-butanediol furazan;

7-[2-(1-哌嗪基)]乙氧基香豆素-3-羧酸1,3-丁二醇呋咱；7-[2-(1-piperazinyl)]ethoxycoumarin-3-carboxylic acid 1,3-butanediol furazan;

7-[2-(4-甲基-1-哌嗪基)]乙氧基香豆素-3-羧酸1,3-丁二醇呋咱；7-[2-(4-Methyl-1-piperazinyl)]ethoxycoumarin-3-carboxylic acid 1,3-butanediolfurazan;

7-[2-(4-乙基-1-哌嗪基)]乙氧基香豆素-3-羧酸1,3-丁二醇呋咱；7-[2-(4-Ethyl-1-piperazinyl)]ethoxycoumarin-3-carboxylic acid 1,3-butanediol furazan;

7-[2-(4-羟乙基-1-哌嗪基)]乙氧基香豆素-3-羧酸1,3-丁二醇呋咱；7-[2-(4-Hydroxyethyl-1-piperazinyl)]ethoxycoumarin-3-carboxylic acid 1,3-butanediol furazan;

7-(2-氨基)乙氧基香豆素-3-羧酸1,4-丁二醇呋咱；7-(2-Amino)ethoxycoumarin-3-carboxylic acid 1,4-butanediol furazan;

7-(2-二甲氨基)乙氧基香豆素-3-羧酸1,4-丁二醇呋咱；7-(2-Dimethylamino)ethoxycoumarin-3-carboxylic acid 1,4-butanediol furazan;

7-(2-二乙氨基)乙氧基香豆素-3-羧酸1,4-丁二醇呋咱；7-(2-Diethylamino)ethoxycoumarin-3-carboxylic acid 1,4-butanediol furazan;

7-(2-苯氨基)乙氧基香豆素-3-羧酸1,4-丁二醇呋咱；7-(2-phenylamino)ethoxycoumarin-3-carboxylic acid 1,4-butanediol furazan;

7-(2-苄氨基)乙氧基香豆素-3-羧酸1,4-丁二醇呋咱；7-(2-Benzylamino)ethoxycoumarin-3-carboxylic acid 1,4-butanediol furazan;

7-(2-苯乙氨基)乙氧基香豆素-3-羧酸1,4-丁二醇呋咱；7-(2-Phenylethylamino)ethoxycoumarin-3-carboxylic acid 1,4-butanediolfurazan;

7-[2-(1-哌啶基)]乙氧基香豆素-3-羧酸1,4-丁二醇呋咱；7-[2-(1-piperidinyl)]ethoxycoumarin-3-carboxylic acid 1,4-butanediolfurazan;

7-[2-(1-吗啡啉基)]乙氧基香豆素-3-羧酸1,4-丁二醇呋咱；7-[2-(1-morpholinyl)]ethoxycoumarin-3-carboxylic acid 1,4-butanediol furazan;

7-[2-(1-哌嗪基)]乙氧基香豆素-3-羧酸1,4-丁二醇呋咱；7-[2-(1-piperazinyl)]ethoxycoumarin-3-carboxylic acid 1,4-butanediolfurazan;

7-[2-(4-甲基-1-哌嗪基)]乙氧基香豆素-3-羧酸1,4-丁二醇呋咱；7-[2-(4-Methyl-1-piperazinyl)]ethoxycoumarin-3-carboxylic acid 1,4-butanediolfurazan;

7-[2-(4-乙基-1-哌嗪基)]乙氧基香豆素-3-羧酸1,4-丁二醇呋咱；7-[2-(4-Ethyl-1-piperazinyl)]ethoxycoumarin-3-carboxylic acid 1,4-butanediol furazan;

7-[2-(4-羟乙基-1-哌嗪基)]乙氧基香豆素-3-羧酸1,4-丁二醇呋咱；7-[2-(4-Hydroxyethyl-1-piperazinyl)]ethoxycoumarin-3-carboxylic acid 1,4-butanediol furazan;

7-(2-氨基)乙氧基香豆素-3-羧酸一缩乙二醇呋咱；7-(2-Amino)ethoxycoumarin-3-carboxylic acid ethylene glycol furazan;

7-(2-二甲氨基)乙氧基香豆素-3-羧酸一缩乙二醇呋咱；7-(2-Dimethylamino)ethoxycoumarin-3-carboxylic acid ethylene glycol furazan;

7-(2-二乙氨基)乙氧基香豆素-3-羧酸一缩乙二醇呋咱；7-(2-Diethylamino)ethoxycoumarin-3-carboxylic acid ethylene glycol furazan;

7-(2-苯氨基)乙氧基香豆素-3-羧酸一缩乙二醇呋咱；7-(2-phenylamino)ethoxycoumarin-3-carboxylic acid ethylene glycol furazan;

7-(2-苄氨基)乙氧基香豆素-3-羧酸一缩乙二醇呋咱；7-(2-Benzylamino)ethoxycoumarin-3-carboxylic acid ethylene glycol furazan;

7-(2-苯乙氨基)乙氧基香豆素-3-羧酸一缩乙二醇呋咱；7-(2-Phenylethylamino)ethoxycoumarin-3-carboxylic acid ethylene glycol furazan;

7-[2-(1-哌啶基)]乙氧基香豆素-3-羧酸一缩乙二醇呋咱；7-[2-(1-piperidinyl)]ethoxycoumarin-3-carboxylic acid ethylene glycol furazan;

7-[2-(1-吗啡啉基)]乙氧基香豆素-3-羧酸一缩乙二醇呋咱；7-[2-(1-morpholinyl)]ethoxycoumarin-3-carboxylic acid ethylene glycol furazan;

7-[2-(1-哌嗪基)]乙氧基香豆素-3-羧酸一缩乙二醇呋咱；7-[2-(1-piperazinyl)]ethoxycoumarin-3-carboxylic acid ethylene glycol furazan;

7-[2-((4-甲基)-1-哌嗪基)]乙氧基香豆素-3-羧酸一缩乙二醇呋咱；7-[2-((4-methyl)-1-piperazinyl)]ethoxycoumarin-3-carboxylic acid ethylene glycol furazan;

7-[2-(4-乙基-1-哌嗪基)]乙氧基香豆素-3-羧酸一缩乙二醇呋咱；7-[2-(4-Ethyl-1-piperazinyl)]ethoxycoumarin-3-carboxylic acid ethylene glycol furazan;

7-[2-(4-羟乙基-1-哌嗪基)]乙氧基香豆素-3-羧酸一缩乙二醇呋咱；7-[2-(4-Hydroxyethyl-1-piperazinyl)]ethoxycoumarin-3-carboxylic acid ethylene glycol furazan;

7-(2-氨基)乙氧基香豆素-3-羧酸1,4-丁炔二醇呋咱；7-(2-Amino)ethoxycoumarin-3-carboxylic acid 1,4-butynediol furazan;

7-(2-二甲氨基)乙氧基香豆素-3-羧酸1,4-丁炔二醇呋咱；7-(2-Dimethylamino)ethoxycoumarin-3-carboxylic acid 1,4-butynediol furazan;

7-(2-二乙氨基)乙氧基香豆素-3-羧酸1,4-丁炔二醇呋咱；7-(2-Diethylamino)ethoxycoumarin-3-carboxylic acid 1,4-butynediol furazan;

7-(2-苯氨基)乙氧基香豆素-3-羧酸1,4-丁炔二醇呋咱；7-(2-phenylamino)ethoxycoumarin-3-carboxylic acid 1,4-butynediol furazan;

7-(2-苄氨基)乙氧基香豆素-3-羧酸1,4-丁炔二醇呋咱；7-(2-Benzylamino)ethoxycoumarin-3-carboxylic acid 1,4-butynediol furazan;

7-(2-苯乙氨基)乙氧基香豆素-3-羧酸1,4-丁炔二醇呋咱；7-(2-Phenylethylamino)ethoxycoumarin-3-carboxylic acid 1,4-butynediol furazan;

7-[2-(1-哌啶基)]乙氧基香豆素-3-羧酸1,4-丁炔二醇呋咱；7-[2-(1-piperidinyl)]ethoxycoumarin-3-carboxylic acid 1,4-butynediol furazan;

7-[2-(1-吗啡啉基)]乙氧基香豆素-3-羧酸1,4-丁炔二醇呋咱；7-[2-(1-morpholinyl)]ethoxycoumarin-3-carboxylic acid 1,4-butynediol furazan;

7-[2-(1-哌嗪基)]乙氧基香豆素-3-羧酸1,4-丁炔二醇呋咱；7-[2-(1-piperazinyl)]ethoxycoumarin-3-carboxylic acid 1,4-butynediol furazan;

7-[2-(4-甲基-1-哌嗪基)]乙氧基香豆素-3-羧酸1,4-丁炔二醇呋咱；7-[2-(4-Methyl-1-piperazinyl)]ethoxycoumarin-3-carboxylic acid 1,4-butynediol furazan;

7-[2-(4-乙基-1-哌嗪基)]乙氧基香豆素-3-羧酸1,4-丁炔二醇呋咱；7-[2-(4-Ethyl-1-piperazinyl)]ethoxycoumarin-3-carboxylic acid 1,4-butynediol furazan;

7-[2-(4-羟乙基-1-哌嗪基)]乙氧基香豆素-3-羧酸1,4-丁炔二醇呋咱；7-[2-(4-Hydroxyethyl-1-piperazinyl)]ethoxycoumarin-3-carboxylic acid 1,4-butynediol furazan;

7-(2-氨基)乙氧基香豆素-3-羧酸对羟基苯乙醇呋咱；7-(2-Amino)ethoxycoumarin-3-carboxylic acid p-hydroxyphenethylfurazan;

7-(2-二甲氨基)乙氧基香豆素-3-羧酸对羟基苯乙醇呋咱；7-(2-Dimethylamino)ethoxycoumarin-3-carboxylic acid p-hydroxyphenethylfurazan;

7-(2-二乙氨基)乙氧基香豆素-3-羧酸对羟基苯乙醇呋咱；7-(2-Diethylamino)ethoxycoumarin-3-carboxylic acid p-hydroxyphenethylfurazan;

7-(2-苯氨基)乙氧基香豆素-3-羧酸对羟基苯乙醇呋咱；7-(2-phenylamino)ethoxycoumarin-3-carboxylic acid p-hydroxyphenylethylfurazan;

7-(2-苄氨基)乙氧基香豆素-3-羧酸对羟基苯乙醇呋咱；7-(2-Benzylamino)ethoxycoumarin-3-carboxylic acid p-hydroxyphenethylfurazan;

7-(2-苯乙氨基)乙氧基香豆素-3-羧酸对羟基苯乙醇呋咱；7-(2-Phenylethylamino)ethoxycoumarin-3-carboxylic acid p-hydroxyphenylethylfurazan;

7-[2-(1-哌啶基)]乙氧基香豆素-3-羧酸对羟基苯乙醇呋咱；7-[2-(1-piperidinyl)]ethoxycoumarin-3-carboxylic acid p-hydroxyphenethylfurazan;

7-[2-(1-吗啡啉基)]乙氧基香豆素-3-羧酸对羟基苯乙醇呋咱；7-[2-(1-morpholinyl)]ethoxycoumarin-3-carboxylic acid p-hydroxyphenethylfurazan;

7-[2-(1-哌嗪基)]乙氧基香豆素-3-羧酸对羟基苯乙醇呋咱；7-[2-(1-piperazinyl)]ethoxycoumarin-3-carboxylic acid p-hydroxyphenethylfurazan;

7-[2-(4-甲基-1-哌嗪基)]乙氧基香豆素-3-羧酸对羟基苯乙醇呋咱；7-[2-(4-Methyl-1-piperazinyl)]ethoxycoumarin-3-carboxylic acid p-hydroxyphenethylfurazan;

7-[2-(4-乙基-1-哌嗪基)]乙氧基香豆素-3-羧酸对羟基苯乙醇呋咱；7-[2-(4-Ethyl-1-piperazinyl)]ethoxycoumarin-3-carboxylic acid p-hydroxyphenethylfurazan;

7-[2-(4-羟乙基-1-哌嗪基)]乙氧基香豆素-3-羧酸对羟基苯乙醇呋咱；7-[2-(4-Hydroxyethyl-1-piperazinyl)]ethoxycoumarin-3-carboxylic acid p-hydroxyphenethylfurazan;

7-(2-氨基)乙氧基香豆素-3-羧酸氨基乙醇呋咱；7-(2-Amino)ethoxycoumarin-3-carboxylic acid aminoethanol furazan;

7-(2-二甲氨基)乙氧基香豆素-3-羧酸氨基乙醇呋咱；7-(2-Dimethylamino)ethoxycoumarin-3-carboxyaminoethanolfurazan;

7-(2-二乙氨基)乙氧基香豆素-3-羧酸氨基乙醇呋咱；7-(2-Diethylamino)ethoxycoumarin-3-carboxylic acid aminoethanol furazan;

7-(2-苯氨基)乙氧基香豆素-3-羧酸氨基乙醇呋咱；7-(2-phenylamino)ethoxycoumarin-3-carboxylic acid aminoethanol furazan;

7-(2-苄氨基)乙氧基香豆素-3-羧酸氨基乙醇呋咱；7-(2-Benzylamino)ethoxycoumarin-3-carboxyaminoethanolfurazan;

7-(2-苯乙氨基)乙氧基香豆素-3-羧酸氨基乙醇呋咱；7-(2-Phenylethylamino)ethoxycoumarin-3-carboxyaminoethanolfurazan;

7-[2-(1-哌啶基)]乙氧基香豆素-3-羧酸氨基乙醇呋咱；7-[2-(1-piperidinyl)]ethoxycoumarin-3-carboxylic acid aminoethanol furazan;

7-[2-(1-吗啡啉基)]乙氧基香豆素-3-羧酸氨基乙醇呋咱；7-[2-(1-morpholinyl)]ethoxycoumarin-3-carboxylic acid aminoethanol furazan;

7-[2-(1-哌嗪基)]乙氧基香豆素-3-羧酸氨基乙醇呋咱；7-[2-(1-piperazinyl)]ethoxycoumarin-3-carboxylic acid aminoethanol furazan;

7-[2-(4-甲基-1-哌嗪基)]乙氧基香豆素-3-羧酸氨基乙醇呋咱；7-[2-(4-Methyl-1-piperazinyl)]ethoxycoumarin-3-carboxylic acid aminoethanol furazan;

7-[2-(4-乙基-1-哌嗪基)]乙氧基香豆素-3-羧酸氨基乙醇呋咱；7-[2-(4-Ethyl-1-piperazinyl)]ethoxycoumarin-3-carboxyaminoethanolfurazan;

7-[2-(4-羟乙基-1-哌嗪基)]乙氧基香豆素-3-羧酸氨基乙醇呋咱；7-[2-(4-Hydroxyethyl-1-piperazinyl)]ethoxycoumarin-3-carboxylic acid aminoethanol furazan;

7-(2-氨基)乙氧基香豆素-3-羧酸氨基丙醇呋咱；7-(2-Amino)ethoxycoumarin-3-carboxylic acid aminopropanol furazan;

7-(2-二甲氨基)乙氧基香豆素-3-羧酸氨基丙醇呋咱；7-(2-Dimethylamino)ethoxycoumarin-3-carboxylic acid aminopropanol furazan;

7-(2-二乙氨基)乙氧基香豆素-3-羧酸氨基丙醇呋咱；7-(2-Diethylamino)ethoxycoumarin-3-carboxylic acid aminopropanol furazan;

7-(2-苯氨基)乙氧基香豆素-3-羧酸氨基丙醇呋咱；7-(2-phenylamino)ethoxycoumarin-3-carboxylic acid aminopropanol furazan;

7-(2-苄氨基)乙氧基香豆素-3-羧酸氨基丙醇呋咱；7-(2-Benzylamino)ethoxycoumarin-3-carboxylic acid aminopropanol furazan;

7-(2-苯乙氨基)乙氧基香豆素-3-羧酸氨基丙醇呋咱；7-(2-Phenylethylamino)ethoxycoumarin-3-carboxylic acid aminopropanol furazan;

7-[2-(1-哌啶基)]乙氧基香豆素-3-羧酸氨基丙醇呋咱；7-[2-(1-piperidinyl)]ethoxycoumarin-3-carboxylic acid aminopropanol furazan;

7-[2-(1-吗啡啉基)]乙氧基香豆素-3-羧酸氨基丙醇呋咱；7-[2-(1-morpholinyl)]ethoxycoumarin-3-carboxylic acid aminopropanol furazan;

7-[2-(1-哌嗪基)]乙氧基香豆素-3-羧酸氨基丙醇呋咱；7-[2-(1-piperazinyl)]ethoxycoumarin-3-carboxylic acid aminopropanol furazan;

7-[2-(4-甲基-1-哌嗪基)]乙氧基香豆素-3-羧酸氨基丙醇呋咱；7-[2-(4-Methyl-1-piperazinyl)]ethoxycoumarin-3-carboxylic acid aminopropanol furazan;

7-[2-(4-乙基-1-哌嗪基)]乙氧基香豆素-3-羧酸氨基丙醇呋咱；7-[2-(4-Ethyl-1-piperazinyl)]ethoxycoumarin-3-carboxylic acid aminopropanol furazan;

7-[2-(4-羟乙基-1-哌嗪基)]乙氧基香豆素-3-羧酸氨基丙醇呋咱；7-[2-(4-Hydroxyethyl-1-piperazinyl)]ethoxycoumarin-3-carboxylic acid aminopropanol furazan;

7-(2-氨基)乙氧基香豆素-3-羧酸异丙醇胺呋咱；7-(2-Amino)ethoxycoumarin-3-carboxylic acid isopropanolamide furazan;

7-(2-二甲氨基)乙氧基香豆素-3-羧酸异丙醇胺呋咱；7-(2-Dimethylamino)ethoxycoumarin-3-carboxylic acid isopropanolamide furazan;

7-(2-二乙氨基)乙氧基香豆素-3-羧酸异丙醇胺呋咱；7-(2-Diethylamino)ethoxycoumarin-3-carboxylic acid isopropanolamide furazan;

7-(2-苯氨基)乙氧基香豆素-3-羧酸异丙醇胺呋咱；7-(2-phenylamino)ethoxycoumarin-3-carboxylic acid isopropanolamine furazan;

7-(2-苄氨基)乙氧基香豆素-3-羧酸异丙醇胺呋咱；7-(2-Benzylamino)ethoxycoumarin-3-carboxylic acid isopropanolamide furazan;

7-(2-苯乙氨基)乙氧基香豆素-3-羧酸异丙醇胺呋咱；7-(2-Phenylethylamino)ethoxycoumarin-3-carboxylic acid isopropanolamide furazan;

7-[2-(1-哌啶基)]乙氧基香豆素-3-羧酸异丙醇胺呋咱；7-[2-(1-piperidinyl)]ethoxycoumarin-3-carboxylic acid isopropanolamide furazan;

7-[2-(1-吗啡啉基)]乙氧基香豆素-3-羧酸异丙醇胺呋咱；7-[2-(1-morpholinyl)]ethoxycoumarin-3-carboxylic acid isopropanolamide furazan;

7-[2-(1-哌嗪基)]乙氧基香豆素-3-羧酸异丙醇胺呋咱；7-[2-(1-piperazinyl)]ethoxycoumarin-3-carboxylic acid isopropanolamide furazan;

7-[2-(4-甲基-1-哌嗪基)]乙氧基香豆素-3-羧酸异丙醇胺呋咱；7-[2-(4-Methyl-1-piperazinyl)]ethoxycoumarin-3-carboxylic acid isopropanolamine furazan;

7-[2-(4-乙基-1-哌嗪基)]乙氧基香豆素-3-羧酸异丙醇胺呋咱；7-[2-(4-Ethyl-1-piperazinyl)]ethoxycoumarin-3-carboxylic acid isopropanolamine furazan;

7-[2-(4-羟乙基-1-哌嗪基)]乙氧基香豆素-3-羧酸异丙醇胺呋咱；7-[2-(4-Hydroxyethyl-1-piperazinyl)]ethoxycoumarin-3-carboxylic acid isopropanolamine furazan;

7-(3-氨基)丙氧基香豆素-3-羧酸1,2-乙二醇呋咱；7-(3-Amino)propoxycoumarin-3-carboxylic acid 1,2-ethylene glycol furazan;

7-(3-二甲氨基)丙氧基香豆素-3-羧酸1,2-乙二醇呋咱；7-(3-Dimethylamino)propoxycoumarin-3-carboxylic acid 1,2-ethylene glycol furazan;

7-(3-二乙氨基)丙氧基香豆素-3-羧酸1,2-乙二醇呋咱；7-(3-Diethylamino)propoxycoumarin-3-carboxylic acid 1,2-ethylene glycol furazan;

7-(3-苯氨基)丙氧基香豆素-3-羧酸1,2-乙二醇呋咱；7-(3-phenylamino)propoxycoumarin-3-carboxylic acid 1,2-ethylene glycol furazan;

7-(3-苄氨基)丙氧基香豆素-3-羧酸1,2-乙二醇呋咱；7-(3-Benzylamino)propoxycoumarin-3-carboxylic acid 1,2-ethylene glycol furazan;

7-(3-苯乙氨基)丙氧基香豆素-3-羧酸1,2-乙二醇呋咱；7-(3-Phenylethylamino)propoxycoumarin-3-carboxylic acid 1,2-ethylene glycol furazan;

7-[3-(1-哌啶基)]丙氧基香豆素-3-羧酸1,2-乙二醇呋咱；7-[3-(1-piperidinyl)]propoxycoumarin-3-carboxylic acid 1,2-ethylene glycol furazan;

7-[3-(1-吗啡啉基)]丙氧基香豆素-3-羧酸1,2-乙二醇呋咱；7-[3-(1-morpholinyl)]propoxycoumarin-3-carboxylic acid 1,2-ethylene glycol furazan;

7-[3-(1-哌嗪基)]丙氧基香豆素-3-羧酸1,2-乙二醇呋咱；7-[3-(1-piperazinyl)]propoxycoumarin-3-carboxylic acid 1,2-ethylene glycol furazan;

7-[3-(4-甲基-1-哌嗪基)]丙氧基香豆素-3-羧酸1,2-乙二醇呋咱；7-[3-(4-Methyl-1-piperazinyl)]propoxycoumarin-3-carboxylic acid 1,2-ethylene glycol furazan;

7-[3-(4-乙基-1-哌嗪基)]丙氧基香豆素-3-羧酸1,2-乙二醇呋咱；7-[3-(4-Ethyl-1-piperazinyl)]propoxycoumarin-3-carboxylic acid 1,2-ethylene glycol furazan;

7-[3-(4-羟乙基-1-哌嗪基)]丙氧基香豆素-3-羧酸1,2-乙二醇呋咱；7-[3-(4-Hydroxyethyl-1-piperazinyl)]propoxycoumarin-3-carboxylic acid 1,2-ethylene glycol furazan;

7-(3-氨基)丙氧基香豆素-3-羧酸1,2-丙二醇呋咱；7-(3-Amino)propoxycoumarin-3-carboxylic acid 1,2-propanediol furazan;

7-(3-二甲氨基)丙氧基香豆素-3-羧酸1,2-丙二醇呋咱；7-(3-Dimethylamino)propoxycoumarin-3-carboxylic acid 1,2-propanediol furazan;

7-(3-二乙氨基)丙氧基香豆素-3-羧酸1,2-丙二醇呋咱；7-(3-Diethylamino)propoxycoumarin-3-carboxylic acid 1,2-propanediol furazan;

7-(3-苯氨基)丙氧基香豆素-3-羧酸1,2-丙二醇呋咱；7-(3-phenylamino)propoxycoumarin-3-carboxylic acid 1,2-propanediol furazan;

7-(3-苄氨基)丙氧基香豆素-3-羧酸1,2-丙二醇呋咱；7-(3-Benzylamino)propoxycoumarin-3-carboxylic acid 1,2-propanediol furazan;

7-(3-苯乙氨基)丙氧基香豆素-3-羧酸1,2-丙二醇呋咱；7-(3-Phenylethylamino)propoxycoumarin-3-carboxylic acid 1,2-propanediol furazan;

7-[3-(1-哌啶基)]丙氧基香豆素-3-羧酸1,2-丙二醇呋咱；7-[3-(1-piperidinyl)]propoxycoumarin-3-carboxylic acid 1,2-propanediol furazan;

7-[3-(1-吗啡啉基)]丙氧基香豆素-3-羧酸1,2-丙二醇呋咱；7-[3-(1-morpholinyl)]propoxycoumarin-3-carboxylic acid 1,2-propanediolfurazan;

7-[3-(1-哌嗪基)]丙氧基香豆素-3-羧酸1,2-丙二醇呋咱；7-[3-(1-piperazinyl)]propoxycoumarin-3-carboxylic acid 1,2-propanediol furazan;

7-[3-(4-甲基-1-哌嗪基)]丙氧基香豆素-3-羧酸1,2-丙二醇呋咱；7-[3-(4-Methyl-1-piperazinyl)]propoxycoumarin-3-carboxylic acid 1,2-propanediolfurazan;

7-[3-(4-乙基-1-哌嗪基)]丙氧基香豆素-3-羧酸1,2-丙二醇呋咱；7-[3-(4-Ethyl-1-piperazinyl)]propoxycoumarin-3-carboxylic acid 1,2-propanediolfurazan;

7-[3-(4-羟乙基-1-哌嗪基)]丙氧基香豆素-3-羧酸1,2-丙二醇呋咱；7-[3-(4-Hydroxyethyl-1-piperazinyl)]propoxycoumarin-3-carboxylic acid 1,2-propanediolfurazan;

7-(3-氨基)丙氧基香豆素-3-羧酸1,3-丙二醇呋咱；7-(3-Amino)propoxycoumarin-3-carboxylic acid 1,3-propanediol furazan;

7-(3-二甲氨基)丙氧基香豆素-3-羧酸1,3-丙二醇呋咱；7-(3-Dimethylamino)propoxycoumarin-3-carboxylic acid 1,3-propanediol furazan;

7-(3-二乙氨基)丙氧基香豆素-3-羧酸1,3-丙二醇呋咱；7-(3-Diethylamino)propoxycoumarin-3-carboxylic acid 1,3-propanediol furazan;

7-(3-苯氨基)丙氧基香豆素-3-羧酸1,3-丙二醇呋咱；7-(3-phenylamino)propoxycoumarin-3-carboxylic acid 1,3-propanediol furazan;

7-(3-苄氨基)丙氧基香豆素-3-羧酸1,3-丙二醇呋咱；7-(3-Benzylamino)propoxycoumarin-3-carboxylic acid 1,3-propanediol furazan;

7-(3-苯乙氨基)丙氧基香豆素-3-羧酸1,3-丙二醇呋咱；7-(3-Phenylethylamino)propoxycoumarin-3-carboxylic acid 1,3-propanediol furazan;

7-[3-(1-哌啶基)]丙氧基香豆素-3-羧酸1,3-丙二醇呋咱；7-[3-(1-piperidinyl)]propoxycoumarin-3-carboxylic acid 1,3-propanediol furazan;

7-[3-(1-吗啡啉基)]丙氧基香豆素-3-羧酸1,3-丙二醇呋咱；7-[3-(1-morpholinyl)]propoxycoumarin-3-carboxylic acid 1,3-propanediol furazan;

7-[3-(1-哌嗪基)]丙氧基香豆素-3-羧酸1,3-丙二醇呋咱；7-[3-(1-piperazinyl)]propoxycoumarin-3-carboxylic acid 1,3-propanediol furazan;

7-[3-(4-甲基-1-哌嗪基)]丙氧基香豆素-3-羧酸1,3-丙二醇呋咱；7-[3-(4-Methyl-1-piperazinyl)]propoxycoumarin-3-carboxylic acid 1,3-propanediolfurazan;

7-[3-(4-乙基-1-哌嗪基)]丙氧基香豆素-3-羧酸1,3-丙二醇呋咱；7-[3-(4-Ethyl-1-piperazinyl)]propoxycoumarin-3-carboxylic acid 1,3-propanediolfurazan;

7-[3-(4-羟乙基-1-哌嗪基)]丙氧基香豆素-3-羧酸1,3-丙二醇呋咱；7-[3-(4-Hydroxyethyl-1-piperazinyl)]propoxycoumarin-3-carboxylic acid 1,3-propanediol furazan;

7-(3-氨基)丙氧基香豆素-3-羧酸1,3-丁二醇呋咱；7-(3-Amino)propoxycoumarin-3-carboxylic acid 1,3-butanediol furazan;

7-(3-二甲氨基)丙氧基香豆素-3-羧酸1,3-丁二醇呋咱；7-(3-Dimethylamino)propoxycoumarin-3-carboxylic acid 1,3-butanediol furazan;

7-(3-二乙氨基)丙氧基香豆素-3-羧酸1,3-丁二醇呋咱；7-(3-Diethylamino)propoxycoumarin-3-carboxylic acid 1,3-butanediol furazan;

7-(3-苯氨基)丙氧基香豆素-3-羧酸1,3-丁二醇呋咱；7-(3-phenylamino)propoxycoumarin-3-carboxylic acid 1,3-butanediol furazan;

7-(3-苄氨基)丙氧基香豆素-3-羧酸1,3-丁二醇呋咱；7-(3-Benzylamino)propoxycoumarin-3-carboxylic acid 1,3-butanediol furazan;

7-(3-苯乙氨基)丙氧基香豆素-3-羧酸1,3-丁二醇呋咱；7-(3-Phenylethylamino)propoxycoumarin-3-carboxylic acid 1,3-butanediol furazan;

7-[3-(1-哌啶基)]丙氧基香豆素-3-羧酸1,3-丁二醇呋咱；7-[3-(1-piperidinyl)]propoxycoumarin-3-carboxylic acid 1,3-butanediol furazan;

7-[3-(1-吗啡啉基)]丙氧基香豆素-3-羧酸1,3-丁二醇呋咱；7-[3-(1-morpholinyl)]propoxycoumarin-3-carboxylic acid 1,3-butanediol furazan;

7-[3-(1-哌嗪基)]丙氧基香豆素-3-羧酸1,3-丁二醇呋咱；7-[3-(1-piperazinyl)]propoxycoumarin-3-carboxylic acid 1,3-butanediol furazan;

7-[3-(4-甲基-1-哌嗪基)]丙氧基香豆素-3-羧酸1,3-丁二醇呋咱；7-[3-(4-Methyl-1-piperazinyl)]propoxycoumarin-3-carboxylic acid 1,3-butanediol furazan;

7-[3-(4-乙基-1-哌嗪基)]丙氧基香豆素-3-羧酸1,3-丁二醇呋咱；7-[3-(4-Ethyl-1-piperazinyl)]propoxycoumarin-3-carboxylic acid 1,3-butanediol furazan;

7-[3-(4-羟乙基-1-哌嗪基)]丙氧基香豆素-3-羧酸1,3-丁二醇呋咱；7-[3-(4-Hydroxyethyl-1-piperazinyl)]propoxycoumarin-3-carboxylic acid 1,3-butanediol furazan;

7-(3-氨基)丙氧基香豆素-3-羧酸1,4-丁二醇呋咱；7-(3-Amino)propoxycoumarin-3-carboxylic acid 1,4-butanediol furazan;

7-(3-二甲氨基)丙氧基香豆素-3-羧酸1,4-丁二醇呋咱；7-(3-Dimethylamino)propoxycoumarin-3-carboxylic acid 1,4-butanediol furazan;

7-(3-二乙氨基)丙氧基香豆素-3-羧酸1,4-丁二醇呋咱；7-(3-Diethylamino)propoxycoumarin-3-carboxylic acid 1,4-butanediol furazan;

7-(3-苯氨基)丙氧基香豆素-3-羧酸1,4-丁二醇呋咱；7-(3-phenylamino)propoxycoumarin-3-carboxylic acid 1,4-butanediol furazan;

7-(3-苄氨基)丙氧基香豆素-3-羧酸1,4-丁二醇呋咱；7-(3-Benzylamino)propoxycoumarin-3-carboxylic acid 1,4-butanediol furazan;

7-(3-苯乙氨基)丙氧基香豆素-3-羧酸1,4-丁二醇呋咱；7-(3-Phenylethylamino)propoxycoumarin-3-carboxylic acid 1,4-butanediol furazan;

7-[3-(1-哌啶基)]丙氧基香豆素-3-羧酸1,4-丁二醇呋咱；7-[3-(1-piperidinyl)]propoxycoumarin-3-carboxylic acid 1,4-butanediol furazan;

7-[3-(1-吗啡啉基)]丙氧基香豆素-3-羧酸1,4-丁二醇呋咱；7-[3-(1-morpholinyl)]propoxycoumarin-3-carboxylic acid 1,4-butanediol furazan;

7-[3-(1-哌嗪基)]丙氧基香豆素-3-羧酸1,4-丁二醇呋咱；7-[3-(1-piperazinyl)]propoxycoumarin-3-carboxylic acid 1,4-butanediol furazan;

7-[3-(4-甲基-1-哌嗪基)]丙氧基香豆素-3-羧酸1,4-丁二醇呋咱；7-[3-(4-Methyl-1-piperazinyl)]propoxycoumarin-3-carboxylic acid 1,4-butanediol furazan;

7-[3-(4-乙基-1-哌嗪基)]丙氧基香豆素-3-羧酸1,4-丁二醇呋咱；7-[3-(4-Ethyl-1-piperazinyl)]propoxycoumarin-3-carboxylic acid 1,4-butanediol furazan;

7-[3-(4-羟乙基-1-哌嗪基)]丙氧基香豆素-3-羧酸1,4-丁二醇呋咱；7-[3-(4-Hydroxyethyl-1-piperazinyl)]propoxycoumarin-3-carboxylic acid 1,4-butanediol furazan;

7-(3-氨基)丙氧基香豆素-3-羧酸一缩乙二醇呋咱；7-(3-Amino)propoxycoumarin-3-carboxylic acid ethylene glycol furazan;

7-(3-二甲氨基)丙氧基香豆素-3-羧酸一缩乙二醇呋咱；7-(3-Dimethylamino)propoxycoumarin-3-carboxylic acid ethylene glycol furazan;

7-(3-二乙氨基)丙氧基香豆素-3-羧酸一缩乙二醇呋咱；7-(3-Diethylamino)propoxycoumarin-3-carboxylic acid ethylene glycol furazan;

7-(3-苯氨基)丙氧基香豆素-3-羧酸一缩乙二醇呋咱；7-(3-phenylamino)propoxycoumarin-3-carboxylic acid ethylene glycol furazan;

7-(3-苄氨基)丙氧基香豆素-3-羧酸一缩乙二醇呋咱；7-(3-Benzylamino)propoxycoumarin-3-carboxylic acid ethylene glycol furazan;

7-(3-苯乙氨基)丙氧基香豆素-3-羧酸一缩乙二醇呋咱；7-(3-Phenylethylamino)propoxycoumarin-3-carboxylic acid ethylene glycol furazan;

7-[3-(1-哌啶基)]丙氧基香豆素-3-羧酸一缩乙二醇呋咱；7-[3-(1-piperidinyl)]propoxycoumarin-3-carboxylic acid ethylene glycol furazan;

7-[3-(1-吗啡啉基)]丙氧基香豆素-3-羧酸一缩乙二醇呋咱；7-[3-(1-morpholinyl)]propoxycoumarin-3-carboxylic acid ethylene glycol furazan;

7-[3-(1-哌嗪基)]丙氧基香豆素-3-羧酸一缩乙二醇呋咱；7-[3-(1-piperazinyl)]propoxycoumarin-3-carboxylic acid ethylene glycol furazan;

7-[3-(4-甲基-1-哌嗪基)]丙氧基香豆素-3-羧酸一缩乙二醇呋咱；7-[3-(4-Methyl-1-piperazinyl)]propoxycoumarin-3-carboxylic acid ethylene glycol furazan;

7-[3-(4-乙基-1-哌嗪基)]丙氧基香豆素-3-羧酸一缩乙二醇呋咱；7-[3-(4-Ethyl-1-piperazinyl)]propoxycoumarin-3-carboxylic acid ethylene glycol furazan;

7-[3-(4-羟乙基-1-哌嗪基)]丙氧基香豆素-3-羧酸一缩乙二醇呋咱；7-[3-(4-Hydroxyethyl-1-piperazinyl)]propoxycoumarin-3-carboxylic acid ethylene glycol furazan;

7-(3-氨基)丙氧基香豆素-3-羧酸1,4-丁炔二醇呋咱；7-(3-Amino)propoxycoumarin-3-carboxylic acid 1,4-butynediol furazan;

7-(3-二甲氨基)丙氧基香豆素-3-羧酸1,4-丁炔二醇呋咱；7-(3-Dimethylamino)propoxycoumarin-3-carboxylic acid 1,4-butynediol furazan;

7-(3-二乙氨基)丙氧基香豆素-3-羧酸1,4-丁炔二醇呋咱；7-(3-Diethylamino)propoxycoumarin-3-carboxylic acid 1,4-butynediol furazan;

7-(3-苯氨基)丙氧基香豆素-3-羧酸1,4-丁炔二醇呋咱；7-(3-phenylamino)propoxycoumarin-3-carboxylic acid 1,4-butynediol furazan;

7-(3-苄氨基)丙氧基香豆素-3-羧酸1,4-丁炔二醇呋咱；7-(3-Benzylamino)propoxycoumarin-3-carboxylic acid 1,4-butynediol furazan;

7-(3-苯乙氨基)丙氧基香豆素-3-羧酸1,4-丁炔二醇呋咱；7-(3-Phenylethylamino)propoxycoumarin-3-carboxylic acid 1,4-butynediol furazan;

7-[3-(1-哌啶基)]丙氧基香豆素-3-羧酸1,4-丁炔二醇呋咱；7-[3-(1-piperidinyl)]propoxycoumarin-3-carboxylic acid 1,4-butynediol furazan;

7-[3-(1-吗啡啉基)]丙氧基香豆素-3-羧酸1,4-丁炔二醇呋咱；7-[3-(1-morpholinyl)]propoxycoumarin-3-carboxylic acid 1,4-butynediol furazan;

7-[3-(1-哌嗪基)]丙氧基香豆素-3-羧酸1,4-丁炔二醇呋咱；7-[3-(1-piperazinyl)]propoxycoumarin-3-carboxylic acid 1,4-butynediol furazan;

7-[3-(4-甲基-1-哌嗪基)]丙氧基香豆素-3-羧酸1,4-丁炔二醇呋咱；7-[3-(4-Methyl-1-piperazinyl)]propoxycoumarin-3-carboxylic acid 1,4-butynediol furazan;

7-[3-(4-乙基-1-哌嗪基)]丙氧基香豆素-3-羧酸1,4-丁炔二醇呋咱；7-[3-(4-Ethyl-1-piperazinyl)]propoxycoumarin-3-carboxylic acid 1,4-butynediol furazan;

7-[3-(4-羟乙基-1-哌嗪基)]丙氧基香豆素-3-羧酸1,4-丁炔二醇呋咱；7-[3-(4-Hydroxyethyl-1-piperazinyl)]propoxycoumarin-3-carboxylic acid 1,4-butynediol furazan;

7-(3-氨基)丙氧基香豆素-3-羧酸对羟基苯乙醇呋咱；7-(3-Amino)propoxycoumarin-3-carboxylic acid p-hydroxyphenethylfurazan;

7-(3-二甲氨基)丙氧基香豆素-3-羧酸对羟基苯乙醇呋咱；7-(3-Dimethylamino)propoxycoumarin-3-carboxylic acid p-hydroxyphenethylfurazan;

7-(3-二乙氨基)丙氧基香豆素-3-羧酸对羟基苯乙醇呋咱；7-(3-Diethylamino)propoxycoumarin-3-carboxylic acid p-hydroxyphenethylfurazan;

7-(3-苯氨基)丙氧基香豆素-3-羧酸对羟基苯乙醇呋咱；7-(3-phenylamino)propoxycoumarin-3-carboxylic acid p-hydroxyphenylethylfurazan;

7-(3-苄氨基)丙氧基香豆素-3-羧酸对羟基苯乙醇呋咱；7-(3-Benzylamino)propoxycoumarin-3-carboxylic acid p-hydroxyphenethylfurazan;

7-(3-苯乙氨基)丙氧基香豆素-3-羧酸对羟基苯乙醇呋咱；7-(3-phenylethylamino)propoxycoumarin-3-carboxylic acid p-hydroxyphenylethylfurazan;

7-[3-(1-哌啶基)]丙氧基香豆素-3-羧酸对羟基苯乙醇呋咱；7-[3-(1-piperidinyl)]propoxycoumarin-3-carboxylic acid p-hydroxyphenethylfurazan;

7-[3-(1-吗啡啉基)]丙氧基香豆素-3-羧酸对羟基苯乙醇呋咱；7-[3-(1-morpholinyl)]propoxycoumarin-3-carboxylic acid p-hydroxyphenethylfurazan;

7-[3-(1-哌嗪基)]丙氧基香豆素-3-羧酸对羟基苯乙醇呋咱；7-[3-(1-piperazinyl)]propoxycoumarin-3-carboxylic acid p-hydroxyphenethylfurazan;

7-[3-(4-甲基-1-哌嗪基)]丙氧基香豆素-3-羧酸对羟基苯乙醇呋咱；7-[3-(4-Methyl-1-piperazinyl)]propoxycoumarin-3-carboxylic acid p-hydroxyphenethylfurazan;

7-[3-(4-乙基-1-哌嗪基)]丙氧基香豆素-3-羧酸对羟基苯乙醇呋咱；7-[3-(4-Ethyl-1-piperazinyl)]propoxycoumarin-3-carboxylic acid p-hydroxyphenethylfurazan;

7-[3-(4-羟乙基-1-哌嗪基)]丙氧基香豆素-3-羧酸对羟基苯乙醇呋咱；7-[3-(4-Hydroxyethyl-1-piperazinyl)]propoxycoumarin-3-carboxylic acid p-hydroxyphenethylfurazan;

7-(3-氨基)丙氧基香豆素-3-羧酸氨基乙醇呋咱；7-(3-Amino)propoxycoumarin-3-carboxylic acid aminoethanol furazan;

7-(3-二甲氨基)丙氧基香豆素-3-羧酸氨基乙醇呋咱；7-(3-Dimethylamino)propoxycoumarin-3-carboxylic acid aminoethanol furazan;

7-(3-二乙氨基)丙氧基香豆素-3-羧酸氨基乙醇呋咱；7-(3-Diethylamino)propoxycoumarin-3-carboxylic acid aminoethanol furazan;

7-(3-苯氨基)丙氧基香豆素-3-羧酸氨基乙醇呋咱；7-(3-phenylamino)propoxycoumarin-3-carboxylic acid aminoethanol furazan;

7-(3-苄氨基)丙氧基香豆素-3-羧酸氨基乙醇呋咱；7-(3-Benzylamino)propoxycoumarin-3-carboxylic acid aminoethanol furazan;

7-(3-苯乙氨基)丙氧基香豆素-3-羧酸氨基乙醇呋咱；7-(3-Phenylethylamino)propoxycoumarin-3-carboxylic acid aminoethanol furazan;

7-[3-(1-哌啶基)]丙氧基香豆素-3-羧酸氨基乙醇呋咱；7-[3-(1-piperidinyl)]propoxycoumarin-3-carboxylic acid aminoethanol furazan;

7-[3-(1-吗啡啉基)]丙氧基香豆素-3-羧酸氨基乙醇呋咱；7-[3-(1-morpholinyl)]propoxycoumarin-3-carboxyaminoethanolfurazan;

7-[3-(1-哌嗪基)]丙氧基香豆素-3-羧酸氨基乙醇呋咱；7-[3-(1-piperazinyl)]propoxycoumarin-3-carboxylic acid aminoethanol furazan;

7-[3-(4-甲基-1-哌嗪基)]丙氧基香豆素-3-羧酸氨基乙醇呋咱；7-[3-(4-Methyl-1-piperazinyl)]propoxycoumarin-3-carboxylic acid aminoethanol furazan;

7-[3-(4-乙基-1-哌嗪基)]丙氧基香豆素-3-羧酸氨基乙醇呋咱；7-[3-(4-Ethyl-1-piperazinyl)]propoxycoumarin-3-carboxyaminoethanolfurazan;

7-[3-(4-羟乙基-1-哌嗪基)]丙氧基香豆素-3-羧酸氨基乙醇呋咱；7-[3-(4-Hydroxyethyl-1-piperazinyl)]propoxycoumarin-3-carboxylic acid aminoethanol furazan;

7-(3-氨基)丙氧基香豆素-3-羧酸氨基丙醇呋咱；7-(3-Amino)propoxycoumarin-3-carboxylic acid aminopropanol furazan;

7-(3-二甲氨基)丙氧基香豆素-3-羧酸氨基丙醇呋咱；7-(3-Dimethylamino)propoxycoumarin-3-carboxylic acid aminopropanol furazan;

7-(3-二乙氨基)丙氧基香豆素-3-羧酸氨基丙醇呋咱；7-(3-Diethylamino)propoxycoumarin-3-carboxylic acid aminopropanol furazan;

7-(3-苯氨基)丙氧基香豆素-3-羧酸氨基丙醇呋咱；7-(3-phenylamino)propoxycoumarin-3-carboxylic acid aminopropanol furazan;

7-(3-苄氨基)丙氧基香豆素-3-羧酸氨基丙醇呋咱；7-(3-Benzylamino)propoxycoumarin-3-carboxylic acid aminopropanol furazan;

7-(3-苯乙氨基)丙氧基香豆素-3-羧酸氨基丙醇呋咱；7-(3-Phenylethylamino)propoxycoumarin-3-carboxylic acid aminopropanol furazan;

7-[3-(1-哌啶基)]丙氧基香豆素-3-羧酸氨基丙醇呋咱；7-[3-(1-piperidinyl)]propoxycoumarin-3-carboxylic acid aminopropanol furazan;

7-[3-(1-吗啡啉基)]丙氧基香豆素-3-羧酸氨基丙醇呋咱；7-[3-(1-morpholinyl)]propoxycoumarin-3-carboxylic acid aminopropanol furazan;

7-[3-(1-哌嗪基)]丙氧基香豆素-3-羧酸氨基丙醇呋咱；7-[3-(1-piperazinyl)]propoxycoumarin-3-carboxylic acid aminopropanol furazan;

7-[3-(4-甲基-1-哌嗪基)]丙氧基香豆素-3-羧酸氨基丙醇呋咱；7-[3-(4-Methyl-1-piperazinyl)]propoxycoumarin-3-carboxylic acid aminopropanol furazan;

7-[3-(4-乙基-1-哌嗪基)]丙氧基香豆素-3-羧酸氨基丙醇呋咱；7-[3-(4-Ethyl-1-piperazinyl)]propoxycoumarin-3-carboxylic acid aminopropanol furazan;

7-[3-(4-羟乙基-1-哌嗪基)]丙氧基香豆素-3-羧酸氨基丙醇呋咱；7-[3-(4-Hydroxyethyl-1-piperazinyl)]propoxycoumarin-3-carboxylic acid aminopropanol furazan;

7-(3-氨基)丙氧基香豆素-3-羧酸异丙醇胺呋咱；7-(3-Amino)propoxycoumarin-3-carboxylic acid isopropanolamide furazan;

7-(3-二甲氨基)丙氧基香豆素-3-羧酸异丙醇胺呋咱；7-(3-Dimethylamino)propoxycoumarin-3-carboxylic acid isopropanolamide furazan;

7-(3-二乙氨基)丙氧基香豆素-3-羧酸异丙醇胺呋咱；7-(3-Diethylamino)propoxycoumarin-3-carboxylic acid isopropanolamine furazan;

7-(3-苯氨基)丙氧基香豆素-3-羧酸异丙醇胺呋咱；7-(3-phenylamino)propoxycoumarin-3-carboxylic acid isopropanolamine furazan;

7-(3-苄氨基)丙氧基香豆素-3-羧酸异丙醇胺呋咱；7-(3-Benzylamino)propoxycoumarin-3-carboxylic acid isopropanolamide furazan;

7-(3-苯乙氨基)丙氧基香豆素-3-羧酸异丙醇胺呋咱；7-(3-Phenylethylamino)propoxycoumarin-3-carboxylic acid isopropanolamide furazan;

7-[3-(1-哌啶基)]丙氧基香豆素-3-羧酸异丙醇胺呋咱；7-[3-(1-piperidinyl)]propoxycoumarin-3-carboxylic acid isopropanolamide furazan;

7-[3-(1-吗啡啉基)]丙氧基香豆素-3-羧酸异丙醇胺呋咱；7-[3-(1-morpholinyl)]propoxycoumarin-3-carboxylic acid isopropanolamide furazan;

7-[3-(1-哌嗪基)]丙氧基香豆素-3-羧酸异丙醇胺呋咱；7-[3-(1-piperazinyl)]propoxycoumarin-3-carboxylic acid isopropanolamide furazan;

7-[3-(4-甲基-1-哌嗪基)]丙氧基香豆素-3-羧酸异丙醇胺呋咱；7-[3-(4-Methyl-1-piperazinyl)]propoxycoumarin-3-carboxylic acid isopropanolamide furazan;

7-[3-(4-乙基-1-哌嗪基)]丙氧基香豆素-3-羧酸异丙醇胺呋咱；7-[3-(4-Ethyl-1-piperazinyl)]propoxycoumarin-3-carboxylic acid isopropanolamine furazan;

7-[3-(4-羟乙基-1-哌嗪基)]丙氧基香豆素-3-羧酸异丙醇胺呋咱；7-[3-(4-Hydroxyethyl-1-piperazinyl)]propoxycoumarin-3-carboxylic acid isopropanolamine furazan;

7-(4-氨基)丁氧基香豆素-3-羧酸1,2-乙二醇呋咱；7-(4-Amino)butoxycoumarin-3-carboxylic acid 1,2-ethylene glycol furazan;

7-(4-二甲氨基)丁氧基香豆素-3-羧酸1,2-乙二醇呋咱；7-(4-Dimethylamino)butoxycoumarin-3-carboxylic acid 1,2-ethylene glycol furazan;

7-(4-二乙氨基)丁氧基香豆素-3-羧酸1,2-乙二醇呋咱；7-(4-Diethylamino)butoxycoumarin-3-carboxylic acid 1,2-ethylene glycol furazan;

7-(4-苯氨基)]丁氧基香豆素-3-羧酸1,2-乙二醇呋咱；7-(4-phenylamino)]butoxycoumarin-3-carboxylic acid 1,2-ethylene glycol furazan;

7-(4-苄氨基)]丁氧基香豆素-3-羧酸1,2-乙二醇呋咱；7-(4-Benzylamino)]butoxycoumarin-3-carboxylic acid 1,2-ethylene glycol furazan;

7-(4-苯乙氨基)]丁氧基香豆素-3-羧酸1,2-乙二醇呋咱；7-(4-phenylethylamino)]butoxycoumarin-3-carboxylic acid 1,2-ethylene glycol furazan;

7-[4-(1-哌啶基)]丁氧基香豆素-3-羧酸1,2-乙二醇呋咱；7-[4-(1-piperidinyl)]butoxycoumarin-3-carboxylic acid 1,2-ethylene glycol furazan;

7-[4-(1-吗啡啉基)]丁氧基香豆素-3-羧酸1,2-乙二醇呋咱；7-[4-(1-morpholinyl)]butoxycoumarin-3-carboxylic acid 1,2-ethylene glycol furazan;

7-[4-(1-哌嗪基)]丁氧基香豆素-3-羧酸1,2-乙二醇呋咱；7-[4-(1-piperazinyl)]butoxycoumarin-3-carboxylic acid 1,2-ethylene glycol furazan;

7-[4-(4-甲基-1-哌嗪基)]丁氧基香豆素-3-羧酸1,2-乙二醇呋咱；7-[4-(4-Methyl-1-piperazinyl)]butoxycoumarin-3-carboxylic acid 1,2-ethylene glycol furazan;

7-[4-(4-乙基-1-哌嗪基)]丁氧基香豆素-3-羧酸1,2-乙二醇呋咱；7-[4-(4-Ethyl-1-piperazinyl)]butoxycoumarin-3-carboxylic acid 1,2-ethylene glycol furazan;

7-[4-(4-羟乙基-1-哌嗪基)]丁氧基香豆素-3-羧酸1,2-乙二醇呋咱；7-[4-(4-Hydroxyethyl-1-piperazinyl)]butoxycoumarin-3-carboxylic acid 1,2-ethylene glycol furazan;

7-(4-氨基)丁氧基香豆素-3-羧酸1,2-丙二醇呋咱；7-(4-Amino)butoxycoumarin-3-carboxylic acid 1,2-propanediol furazan;

7-(4-二甲氨基)丁氧基香豆素-3-羧酸1,2-丙二醇呋咱；7-(4-Dimethylamino)butoxycoumarin-3-carboxylic acid 1,2-propanediol furazan;

7-(4-二乙氨基)丁氧基香豆素-3-羧酸1,2-丙二醇呋咱；7-(4-diethylamino)butoxycoumarin-3-carboxylic acid 1,2-propanediol furazan;

7-(4-苯氨基)]丁氧基香豆素-3-羧酸1,2-丙二醇呋咱；7-(4-phenylamino)]butoxycoumarin-3-carboxylic acid 1,2-propanediol furazan;

7-(4-苄氨基)]丁氧基香豆素-3-羧酸1,2-丙二醇呋咱；7-(4-Benzylamino)]butoxycoumarin-3-carboxylic acid 1,2-propanediol furazan;

7-(4-苯乙氨基)]丁氧基香豆素-3-羧酸1,2-丙二醇呋咱；7-(4-phenylethylamino)]butoxycoumarin-3-carboxylic acid 1,2-propanediol furazan;

7-[4-(1-哌啶基)]丁氧基香豆素-3-羧酸1,2-丙二醇呋咱；7-[4-(1-piperidinyl)]butoxycoumarin-3-carboxylic acid 1,2-propanediolfurazan;

7-[4-(1-吗啡啉基)]丁氧基香豆素-3-羧酸1,2-丙二醇呋咱；7-[4-(1-morpholinyl)]butoxycoumarin-3-carboxylic acid 1,2-propanediol furazan;

7-[4-(1-哌嗪基)]丁氧基香豆素-3-羧酸1,2-丙二醇呋咱；7-[4-(1-piperazinyl)]butoxycoumarin-3-carboxylic acid 1,2-propanediol furazan;

7-[4-(4-甲基-1-哌嗪基)]丁氧基香豆素-3-羧酸1,2-丙二醇呋咱；7-[4-(4-Methyl-1-piperazinyl)]butoxycoumarin-3-carboxylic acid 1,2-propanediolfurazan;

7-[4-(4-乙基-1-哌嗪基)]丁氧基香豆素-3-羧酸1,2-丙二醇呋咱；7-[4-(4-Ethyl-1-piperazinyl)]butoxycoumarin-3-carboxylic acid 1,2-propanediol furazan;

7-[4-(4-羟乙基-1-哌嗪基)]丁氧基香豆素-3-羧酸1,2-丙二醇呋咱；7-[4-(4-Hydroxyethyl-1-piperazinyl)]butoxycoumarin-3-carboxylic acid 1,2-propanediol furazan;

7-(4-氨基)丁氧基香豆素-3-羧酸1,3-丙二醇呋咱；7-(4-Amino)butoxycoumarin-3-carboxylic acid 1,3-propanediol furazan;

7-(4-二甲氨基)丁氧基香豆素-3-羧酸1,3-丙二醇呋咱；7-(4-Dimethylamino)butoxycoumarin-3-carboxylic acid 1,3-propanediol furazan;

7-(4-二乙氨基)丁氧基香豆素-3-羧酸1,3-丙二醇呋咱；7-(4-Diethylamino)butoxycoumarin-3-carboxylic acid 1,3-propanediol furazan;

7-(4-苯氨基)]丁氧基香豆素-3-羧酸1,3-丙二醇呋咱；7-(4-phenylamino)]butoxycoumarin-3-carboxylic acid 1,3-propanediol furazan;

7-(4-苄氨基)]丁氧基香豆素-3-羧酸1,3-丙二醇呋咱；7-(4-Benzylamino)]butoxycoumarin-3-carboxylic acid 1,3-propanediol furazan;

7-(4-苯乙氨基)]丁氧基香豆素-3-羧酸1,3-丙二醇呋咱；7-(4-phenylethylamino)]butoxycoumarin-3-carboxylic acid 1,3-propanediol furazan;

7-[4-(1-哌啶基)]丁氧基香豆素-3-羧酸1,3-丙二醇呋咱；7-[4-(1-piperidinyl)]butoxycoumarin-3-carboxylic acid 1,3-propanediol furazan;

7-[4-(1-吗啡啉基)]丁氧基香豆素-3-羧酸1,3-丙二醇呋咱；7-[4-(1-morpholinyl)]butoxycoumarin-3-carboxylic acid 1,3-propanediol furazan;

7-[4-(1-哌嗪基)]丁氧基香豆素-3-羧酸1,3-丙二醇呋咱；7-[4-(1-piperazinyl)]butoxycoumarin-3-carboxylic acid 1,3-propanediol furazan;

7-[4-(4-甲基-1-哌嗪基)]丁氧基香豆素-3-羧酸1,3-丙二醇呋咱；7-[4-(4-Methyl-1-piperazinyl)]butoxycoumarin-3-carboxylic acid 1,3-propanediolfurazan;

7-[4-(4-乙基-1-哌嗪基)]丁氧基香豆素-3-羧酸1,3-丙二醇呋咱；7-[4-(4-Ethyl-1-piperazinyl)]butoxycoumarin-3-carboxylic acid 1,3-propanediol furazan;

7-[4-(4-羟乙基-1-哌嗪基)]丁氧基香豆素-3-羧酸1,3-丙二醇呋咱；7-[4-(4-Hydroxyethyl-1-piperazinyl)]butoxycoumarin-3-carboxylic acid 1,3-propanediol furazan;

7-(4-氨基)丁氧基香豆素-3-羧酸1,3-丁二醇呋咱；7-(4-Amino)butoxycoumarin-3-carboxylic acid 1,3-butanediol furazan;

7-(4-二甲氨基)丁氧基香豆素-3-羧酸1,3-丁二醇呋咱；7-(4-Dimethylamino)butoxycoumarin-3-carboxylic acid 1,3-butanediol furazan;

7-(4-二乙氨基)丁氧基香豆素-3-羧酸1,3-丁二醇呋咱；7-(4-Diethylamino)butoxycoumarin-3-carboxylic acid 1,3-butanediol furazan;

7-(4-苯氨基)]丁氧基香豆素-3-羧酸1,3-丁二醇呋咱；7-(4-phenylamino)]butoxycoumarin-3-carboxylic acid 1,3-butanediol furazan;

7-(4-苄氨基)]丁氧基香豆素-3-羧酸1,3-丁二醇呋咱；7-(4-Benzylamino)]butoxycoumarin-3-carboxylic acid 1,3-butanediol furazan;

7-(4-苯乙氨基)]丁氧基香豆素-3-羧酸1,3-丁二醇呋咱；7-(4-phenylethylamino)]butoxycoumarin-3-carboxylic acid 1,3-butanediol furazan;

7-[4-(1-哌啶基)]丁氧基香豆素-3-羧酸1,3-丁二醇呋咱；7-[4-(1-piperidinyl)]butoxycoumarin-3-carboxylic acid 1,3-butanediolfurazan;

7-[4-(1-吗啡啉基)]丁氧基香豆素-3-羧酸1,3-丁二醇呋咱；7-[4-(1-morpholinyl)]butoxycoumarin-3-carboxylic acid 1,3-butanediolfurazan;

7-[4-(1-哌嗪基)]丁氧基香豆素-3-羧酸1,3-丁二醇呋咱；7-[4-(1-piperazinyl)]butoxycoumarin-3-carboxylic acid 1,3-butanediolfurazan;

7-[4-(4-甲基-1-哌嗪基)]丁氧基香豆素-3-羧酸1,3-丁二醇呋咱；7-[4-(4-Methyl-1-piperazinyl)]butoxycoumarin-3-carboxylic acid 1,3-butanediolfurazan;

7-[4-(4-乙基-1-哌嗪基)]丁氧基香豆素-3-羧酸1,3-丁二醇呋咱；7-[4-(4-Ethyl-1-piperazinyl)]butoxycoumarin-3-carboxylic acid 1,3-butanediolfurazan;

7-[4-(4-羟乙基-1-哌嗪基)]丁氧基香豆素-3-羧酸1,3-丁二醇呋咱；7-[4-(4-Hydroxyethyl-1-piperazinyl)]butoxycoumarin-3-carboxylic acid 1,3-butanediol furazan;

7-(4-氨基)丁氧基香豆素-3-羧酸1,4-丁二醇呋咱；7-(4-Amino)butoxycoumarin-3-carboxylic acid 1,4-butanediol furazan;

7-(4-二甲氨基)丁氧基香豆素-3-羧酸1,4-丁二醇呋咱；7-(4-Dimethylamino)butoxycoumarin-3-carboxylic acid 1,4-butanediol furazan;

7-(4-二乙氨基)丁氧基香豆素-3-羧酸1,4-丁二醇呋咱；7-(4-diethylamino)butoxycoumarin-3-carboxylic acid 1,4-butanediol furazan;

7-(4-苯氨基)]丁氧基香豆素-3-羧酸1,4-丁二醇呋咱；7-(4-phenylamino)]butoxycoumarin-3-carboxylic acid 1,4-butanediol furazan;

7-(4-苄氨基)]丁氧基香豆素-3-羧酸1,4-丁二醇呋咱；7-(4-Benzylamino)]butoxycoumarin-3-carboxylic acid 1,4-butanediol furazan;

7-(4-苯乙氨基)]丁氧基香豆素-3-羧酸1,4-丁二醇呋咱；7-(4-phenylethylamino)]butoxycoumarin-3-carboxylic acid 1,4-butanediolfurazan;

7-[4-(1-哌啶基)]丁氧基香豆素-3-羧酸1,4-丁二醇呋咱；7-[4-(1-piperidinyl)]butoxycoumarin-3-carboxylic acid 1,4-butanediolfurazan;

7-[4-(1-吗啡啉基)]丁氧基香豆素-3-羧酸1,4-丁二醇呋咱；7-[4-(1-morpholinyl)]butoxycoumarin-3-carboxylic acid 1,4-butanediol furazan;

7-[4-(1-哌嗪基)]丁氧基香豆素-3-羧酸1,4-丁二醇呋咱；7-[4-(1-piperazinyl)]butoxycoumarin-3-carboxylic acid 1,4-butanediolfurazan;

7-[4-(4-甲基-1-哌嗪基)]丁氧基香豆素-3-羧酸1,4-丁二醇呋咱；7-[4-(4-Methyl-1-piperazinyl)]butoxycoumarin-3-carboxylic acid 1,4-butanediolfurazan;

7-[4-(4-乙基-1-哌嗪基)]丁氧基香豆素-3-羧酸1,4-丁二醇呋咱；7-[4-(4-Ethyl-1-piperazinyl)]butoxycoumarin-3-carboxylic acid 1,4-butanediolfurazan;

7-[4-(4-羟乙基-1-哌嗪基)]丁氧基香豆素-3-羧酸1,4-丁二醇呋咱；7-[4-(4-Hydroxyethyl-1-piperazinyl)]butoxycoumarin-3-carboxylic acid 1,4-butanediol furazan;

7-(4-氨基)丁氧基香豆素-3-羧酸一缩乙二醇呋咱；7-(4-Amino)butoxycoumarin-3-carboxylic acid ethylene glycol furazan;

7-(4-二甲氨基)丁氧基香豆素-3-羧酸一缩乙二醇呋咱；7-(4-Dimethylamino)butoxycoumarin-3-carboxylic acid ethylene glycol furazan;

7-(4-二乙氨基)丁氧基香豆素-3-羧酸一缩乙二醇呋咱；7-(4-Diethylamino)butoxycoumarin-3-carboxylic acid ethylene glycol furazan;

7-(4-苯氨基)]丁氧基香豆素-3-羧酸一缩乙二醇呋咱；7-(4-phenylamino)]butoxycoumarin-3-carboxylic acid ethylene glycol furazan;

7-(4-苄氨基)]丁氧基香豆素-3-羧酸一缩乙二醇呋咱；7-(4-Benzylamino)]butoxycoumarin-3-carboxylic acid ethylene glycol furazan;

7-(4-苯乙氨基)]丁氧基香豆素-3-羧酸一缩乙二醇呋咱；7-(4-phenylethylamino)]butoxycoumarin-3-carboxylic acid ethylene glycol furazan;

7-[4-(1-哌啶基)]丁氧基香豆素-3-羧酸一缩乙二醇呋咱；7-[4-(1-piperidinyl)]butoxycoumarin-3-carboxylic acid ethylene glycol furazan;

7-[4-(1-吗啡啉基)]丁氧基香豆素-3-羧酸一缩乙二醇呋咱；7-[4-(1-morpholinyl)]butoxycoumarin-3-carboxylic acid ethylene glycol furazan;

7-[4-(1-哌嗪基)]丁氧基香豆素-3-羧酸一缩乙二醇呋咱；7-[4-(1-piperazinyl)]butoxycoumarin-3-carboxylic acid ethylene glycol furazan;

7-[4-(4-甲基-1-哌嗪基)]丁氧基香豆素-3-羧酸一缩乙二醇呋咱；7-[4-(4-Methyl-1-piperazinyl)]butoxycoumarin-3-carboxylic acid ethylene glycol furazan;

7-[4-(4-乙基-1-哌嗪基)]丁氧基香豆素-3-羧酸一缩乙二醇呋咱；7-[4-(4-Ethyl-1-piperazinyl)]butoxycoumarin-3-carboxylic acid ethylene glycol furazan;

7-[4-(4-羟乙基-1-哌嗪基)]丁氧基香豆素-3-羧酸一缩乙二醇呋咱；7-[4-(4-Hydroxyethyl-1-piperazinyl)]butoxycoumarin-3-carboxylic acid ethylene glycol furazan;

7-(4-氨基)丁氧基香豆素-3-羧酸1,4-丁炔二醇呋咱；7-(4-Amino)butoxycoumarin-3-carboxylic acid 1,4-butynediol furazan;

7-(4-二甲氨基)丁氧基香豆素-3-羧酸1,4-丁炔二醇呋咱；7-(4-Dimethylamino)butoxycoumarin-3-carboxylic acid 1,4-butynediol furazan;

7-(4-二乙氨基)丁氧基香豆素-3-羧酸1,4-丁炔二醇呋咱；7-(4-Diethylamino)butoxycoumarin-3-carboxylic acid 1,4-butynediol furazan;

7-(4-苯氨基)]丁氧基香豆素-3-羧酸1,4-丁炔二醇呋咱；7-(4-phenylamino)]butoxycoumarin-3-carboxylic acid 1,4-butynediol furazan;

7-(4-苄氨基)]丁氧基香豆素-3-羧酸1,4-丁炔二醇呋咱；7-(4-Benzylamino)]butoxycoumarin-3-carboxylic acid 1,4-butynediol furazan;

7-(4-苯乙氨基)]丁氧基香豆素-3-羧酸1,4-丁炔二醇呋咱；7-(4-phenylethylamino)]butoxycoumarin-3-carboxylic acid 1,4-butynediol furazan;

7-[4-(1-哌啶基)]丁氧基香豆素-3-羧酸1,4-丁炔二醇呋咱；7-[4-(1-piperidinyl)]butoxycoumarin-3-carboxylic acid 1,4-butynediol furazan;

7-[4-(1-吗啡啉基)]丁氧基香豆素-3-羧酸1,4-丁炔二醇呋咱；7-[4-(1-morpholinyl)]butoxycoumarin-3-carboxylic acid 1,4-butynediol furazan;

7-[4-(1-哌嗪基)]丁氧基香豆素-3-羧酸1,4-丁炔二醇呋咱；7-[4-(1-piperazinyl)]butoxycoumarin-3-carboxylic acid 1,4-butynediol furazan;

7-[4-(4-甲基-1-哌嗪基)]丁氧基香豆素-3-羧酸1,4-丁炔二醇呋咱；7-[4-(4-Methyl-1-piperazinyl)]butoxycoumarin-3-carboxylic acid 1,4-butynediol furazan;

7-[4-(4-乙基-1-哌嗪基)]丁氧基香豆素-3-羧酸1,4-丁炔二醇呋咱；7-[4-(4-Ethyl-1-piperazinyl)]butoxycoumarin-3-carboxylic acid 1,4-butynediol furazan;

7-[4-(4-羟乙基-1-哌嗪基)]丁氧基香豆素-3-羧酸1,4-丁炔二醇呋咱；7-[4-(4-Hydroxyethyl-1-piperazinyl)]butoxycoumarin-3-carboxylic acid 1,4-butynediol furazan;

7-(4-氨基)丁氧基香豆素-3-羧酸对羟基苯乙醇呋咱；7-(4-Amino)butoxycoumarin-3-carboxylic acid p-hydroxyphenethylfurazan;

7-(4-二甲氨基)丁氧基香豆素-3-羧酸对羟基苯乙醇呋咱；7-(4-Dimethylamino)butoxycoumarin-3-carboxylic acid p-hydroxyphenethylfurazan;

7-(4-二乙氨基)丁氧基香豆素-3-羧酸对羟基苯乙醇呋咱；7-(4-Diethylamino)butoxycoumarin-3-carboxylic acid p-hydroxyphenethylfurazan;

7-(4-苯氨基)]丁氧基香豆素-3-羧酸对羟基苯乙醇呋咱；7-(4-phenylamino)]butoxycoumarin-3-carboxylic acid p-hydroxyphenylethylfurazan;

7-(4-苄氨基)]丁氧基香豆素-3-羧酸对羟基苯乙醇呋咱；7-(4-Benzylamino)]butoxycoumarin-3-carboxylic acid p-hydroxyphenethylfurazan;

7-(4-苯乙氨基)]丁氧基香豆素-3-羧酸对羟基苯乙醇呋咱；7-(4-phenylethylamino)]butoxycoumarin-3-carboxylic acid p-hydroxyphenylethylfurazan;

7-[4-(1-哌啶基)]丁氧基香豆素-3-羧酸对羟基苯乙醇呋咱；7-[4-(1-piperidinyl)]butoxycoumarin-3-carboxylic acid p-hydroxyphenethylfurazan;

7-[4-(1-吗啡啉基)]丁氧基香豆素-3-羧酸对羟基苯乙醇呋咱；7-[4-(1-morpholinyl)]butoxycoumarin-3-carboxylic acid p-hydroxyphenethylfurazan;

7-[4-(1-哌嗪基)]丁氧基香豆素-3-羧酸对羟基苯乙醇呋咱；7-[4-(1-piperazinyl)]butoxycoumarin-3-carboxylic acid p-hydroxyphenethylfurazan;

7-[4-(4-甲基-1-哌嗪基)]丁氧基香豆素-3-羧酸对羟基苯乙醇呋咱；7-[4-(4-Methyl-1-piperazinyl)]butoxycoumarin-3-carboxylic acid p-hydroxyphenethylfurazan;

7-[4-(4-乙基-1-哌嗪基)]丁氧基香豆素-3-羧酸对羟基苯乙醇呋咱；7-[4-(4-Ethyl-1-piperazinyl)]butoxycoumarin-3-carboxylic acid p-hydroxyphenethylfurazan;

7-[4-(4-羟乙基-1-哌嗪基)]丁氧基香豆素-3-羧酸对羟基苯乙醇呋咱；7-[4-(4-Hydroxyethyl-1-piperazinyl)]butoxycoumarin-3-carboxylic acid p-hydroxyphenethylfurazan;

7-(4-氨基)丁氧基香豆素-3-羧酸氨基乙醇呋咱；7-(4-Amino)butoxycoumarin-3-carboxylic acid aminoethanol furazan;

7-(4-二甲氨基)丁氧基香豆素-3-羧酸氨基乙醇呋咱；7-(4-Dimethylamino)butoxycoumarin-3-carboxylic acid aminoethanol furazan;

7-(4-二乙氨基)丁氧基香豆素-3-羧酸氨基乙醇呋咱；7-(4-Diethylamino)butoxycoumarin-3-carboxylic acid aminoethanol furazan;

7-(4-苯氨基)]丁氧基香豆素-3-羧酸氨基乙醇呋咱；7-(4-phenylamino)]butoxycoumarin-3-carboxyaminoethanolfurazan;

7-(4-苄氨基)]丁氧基香豆素-3-羧酸氨基乙醇呋咱；7-(4-Benzylamino)]butoxycoumarin-3-carboxyaminoethanolfurazan;

7-(4-苯乙氨基)]丁氧基香豆素-3-羧酸氨基乙醇呋咱；7-(4-phenylethylamino)]butoxycoumarin-3-carboxyaminoethanolfurazan;

7-[4-(1-哌啶基)]丁氧基香豆素-3-羧酸氨基乙醇呋咱；7-[4-(1-piperidinyl)]butoxycoumarin-3-carboxylic acid aminoethanol furazan;

7-[4-(1-吗啡啉基)]丁氧基香豆素-3-羧酸氨基乙醇呋咱；7-[4-(1-morpholinyl)]butoxycoumarin-3-carboxylic acid aminoethanol furazan;

7-[4-(1-哌嗪基)]丁氧基香豆素-3-羧酸氨基乙醇呋咱；7-[4-(1-piperazinyl)]butoxycoumarin-3-carboxylic acid aminoethanol furazan;

7-[4-(4-甲基-1-哌嗪基)]丁氧基香豆素-3-羧酸氨基乙醇呋咱；7-[4-(4-Methyl-1-piperazinyl)]butoxycoumarin-3-carboxyaminoethanolfurazan;

7-[4-(4-乙基-1-哌嗪基)]丁氧基香豆素-3-羧酸氨基乙醇呋咱；7-[4-(4-Ethyl-1-piperazinyl)]butoxycoumarin-3-carboxylic acid aminoethanol furazan;

7-[4-(4-羟乙基-1-哌嗪基)]丁氧基香豆素-3-羧酸氨基乙醇呋咱；7-[4-(4-Hydroxyethyl-1-piperazinyl)]butoxycoumarin-3-carboxylic acid aminoethanol furazan;

7-(4-氨基)丁氧基香豆素-3-羧酸氨基丙醇呋咱；7-(4-Amino)butoxycoumarin-3-carboxylic acid aminopropanol furazan;

7-(4-二甲氨基)丁氧基香豆素-3-羧酸氨基丙醇呋咱；7-(4-Dimethylamino)butoxycoumarin-3-carboxylic acid aminopropanol furazan;

7-(4-二乙氨基)丁氧基香豆素-3-羧酸氨基丙醇呋咱；7-(4-Diethylamino)butoxycoumarin-3-carboxylic acid aminopropanol furazan;

7-(4-苯氨基)]丁氧基香豆素-3-羧酸氨基丙醇呋咱；7-(4-phenylamino)]butoxycoumarin-3-carboxylic acid aminopropanol furazan;

7-(4-苄氨基)]丁氧基香豆素-3-羧酸氨基丙醇呋咱；7-(4-Benzylamino)]butoxycoumarin-3-carboxylic acid aminopropanol furazan;

7-(4-苯乙氨基)]丁氧基香豆素-3-羧酸氨基丙醇呋咱；7-(4-Phenylethylamino)]butoxycoumarin-3-carboxylic acid aminopropanol furazan;

7-[4-(1-哌啶基)]丁氧基香豆素-3-羧酸氨基丙醇呋咱；7-[4-(1-piperidinyl)]butoxycoumarin-3-carboxylic acid aminopropanol furazan;

7-[4-(1-吗啡啉基)]丁氧基香豆素-3-羧酸氨基丙醇呋咱；7-[4-(1-morpholinyl)]butoxycoumarin-3-carboxylic acid aminopropanol furazan;

7-[4-(1-哌嗪基)]丁氧基香豆素-3-羧酸氨基丙醇呋咱；7-[4-(1-piperazinyl)]butoxycoumarin-3-carboxylic acid aminopropanol furazan;

7-[4-(4-甲基-1-哌嗪基)]丁氧基香豆素-3-羧酸氨基丙醇呋咱；7-[4-(4-Methyl-1-piperazinyl)]butoxycoumarin-3-carboxylic acid aminopropanol furazan;

7-[4-(4-乙基-1-哌嗪基)]丁氧基香豆素-3-羧酸氨基丙醇呋咱；7-[4-(4-Ethyl-1-piperazinyl)]butoxycoumarin-3-carboxylic acid aminopropanol furazan;

7-[4-(4-羟乙基-1-哌嗪基)]丁氧基香豆素-3-羧酸氨基丙醇呋咱；7-[4-(4-Hydroxyethyl-1-piperazinyl)]butoxycoumarin-3-carboxylic acid aminopropanol furazan;

7-(4-氨基)丁氧基香豆素-3-羧酸异丙醇胺呋咱；7-(4-Amino)butoxycoumarin-3-carboxylic acid isopropanolamide furazan;

7-(4-二甲氨基)丁氧基香豆素-3-羧酸异丙醇胺呋咱；7-(4-Dimethylamino)butoxycoumarin-3-carboxylic acid isopropanolamide furazan;

7-(4-二乙氨基)丁氧基香豆素-3-羧酸异丙醇胺呋咱；7-(4-Diethylamino)butoxycoumarin-3-carboxylic acid isopropanolamine furazan;

7-(4-苯氨基)]丁氧基香豆素-3-羧酸异丙醇胺呋咱；7-(4-phenylamino)]butoxycoumarin-3-carboxylic acid isopropanolamine furazan;

7-(4-苄氨基)]丁氧基香豆素-3-羧酸氨基丙醇呋咱；7-(4-Benzylamino)]butoxycoumarin-3-carboxylic acid aminopropanol furazan;

7-(4-苯乙氨基)]丁氧基香豆素-3-羧酸异丙醇胺呋咱；7-(4-phenylethylamino)]butoxycoumarin-3-carboxylic acid isopropanolamine furazan;

7-[4-(1-哌啶基)]丁氧基香豆素-3-羧酸异丙醇胺呋咱；7-[4-(1-piperidinyl)]butoxycoumarin-3-carboxylic acid isopropanolamide furazan;

7-[4-(1-吗啡啉基)]丁氧基香豆素-3-羧酸异丙醇胺呋咱；7-[4-(1-morpholinyl)]butoxycoumarin-3-carboxylic acid isopropanolamide furazan;

7-[4-(1-哌嗪基)]丁氧基香豆素-3-羧酸异丙醇胺呋咱；7-[4-(1-piperazinyl)]butoxycoumarin-3-carboxylic acid isopropanolamide furazan;

7-[4-((4-甲基)-1-哌嗪基)]丁氧基香豆素-3-羧酸异丙醇胺呋咱；7-[4-((4-methyl)-1-piperazinyl)]butoxycoumarin-3-carboxylic acid isopropanolamine furazan;

7-[4-(4-乙基-1-哌嗪基)]丁氧基香豆素-3-羧酸异丙醇胺呋咱；7-[4-(4-Ethyl-1-piperazinyl)]butoxycoumarin-3-carboxylic acid isopropanolamine furazan;

7-[4-(4-羟乙基-1-哌嗪基)]丁氧基香豆素-3-羧酸异丙醇胺呋咱；7-[4-(4-Hydroxyethyl-1-piperazinyl)]butoxycoumarin-3-carboxylic acid isopropanolamine furazan;

具体地讲，通式I、Ⅱ中所示的NO供体型香豆素衍生物进一步优选自下列化合物：Specifically, the NO-donating coumarin derivatives shown in the general formulas I and II are further preferably selected from the following compounds:

香豆素-3-羧酸-1,3-丙二醇呋咱(I1)(化合物编号：I1，下同)；Coumarin-3-carboxylic acid-1,3-propanediol furazan (I 1 ) (compound number: I 1 , the same below);

香豆素-3-羧酸-1,4-丁二醇呋咱(I2)；Coumarin-3-carboxylic acid-1,4-butanediol furazan (I 2 );

香豆素-3-羧酸一缩乙二醇呋咱(I3)；Coumarin-3-carboxylic acid ethylene glycol furazan (I 3 );

香豆素-3-羧酸-1,4-丁炔二醇呋咱(I4)；Coumarin-3-carboxylic acid-1,4-butynediol furazan (I 4 );

香豆素-3-羧酸对羟基苯乙醇呋咱(I5)；Coumarin-3-carboxylic acid p-hydroxyphenylethylfurazan (I 5 );

香豆素-3-羧氨基乙醇呋咱(I6)；Coumarin-3-carboxyaminoethanolfurazan (I 6 );

香豆素-3-羧酸氨基丙醇呋咱(I7)；Coumarin-3-carboxyaminopropanolfurazan (I 7 );

7-(3-二乙氨基)丙氧基香豆素-3-羧酸1,3-丙二醇呋咱(Ⅱ1)；7-(3-Diethylamino)propoxycoumarin-3-carboxylic acid 1,3-propanediol furazan (Ⅱ 1 );

7-(3-苄氨基)丙氧基香豆素-3-羧酸1,3-丙二醇呋咱(Ⅱ2)；7-(3-Benzylamino)propoxycoumarin-3-carboxylic acid 1,3-propanediol furazan (Ⅱ 2 );

7-[3-(1-吗啡啉基)]丙氧基香豆素-3-羧酸1,3-丙二醇呋咱(Ⅱ3)；7-[3-(1-morpholinyl)]propoxycoumarin-3-carboxylic acid 1,3-propanediol furazan (Ⅱ 3 );

7-[3-(4-甲基-1-哌嗪基)]丙氧基香豆素-3-羧酸1,3-丙二醇呋咱(Ⅱ4)；7-[3-(4-methyl-1-piperazinyl)]propoxycoumarin-3-carboxylic acid 1,3-propanediol furazan (Ⅱ 4 );

7-[3-(4-乙基-1-哌嗪基)]丙氧基香豆素-3-羧酸1,3-丙二醇呋咱(Ⅱ5)；7-[3-(4-Ethyl-1-piperazinyl)]propoxycoumarin-3-carboxylic acid 1,3-propanediol furazan (Ⅱ 5 );

7-[3-(4-羟乙基-1-哌嗪基)]丙氧基香豆素-3-羧酸1,3-丙二醇呋咱(Ⅱ6)；7-[3-(4-Hydroxyethyl-1-piperazinyl)]propoxycoumarin-3-carboxylic acid 1,3-propanediol furazan (Ⅱ 6 );

7-(3-二乙氨基)丙氧基香豆素-3-羧酸1,4-丁二醇呋咱(Ⅱ7)；7-(3-Diethylamino)propoxycoumarin-3-carboxylic acid 1,4-butanediol furazan (Ⅱ 7 );

7-(3-苄氨基)丙氧基香豆素-3-羧酸1,4-丁二醇呋咱(Ⅱ8)；7-(3-Benzylamino)propoxycoumarin-3-carboxylic acid 1,4-butanediol furazan (Ⅱ 8 );

7-[3-(1-哌啶基)]丙氧基香豆素-3-羧酸1,4-丁二醇呋咱(Ⅱ9)；7-[3-(1-piperidinyl)]propoxycoumarin-3-carboxylic acid 1,4-butanediol furazan (Ⅱ 9 );

7-[3-(1-吗啡啉基)]丙氧基香豆素-3-羧酸1,4-丁二醇呋咱(Ⅱ10)；7-[3-(1-morpholinyl)]propoxycoumarin-3-carboxylic acid 1,4-butanediol furazan (Ⅱ 10 );

7-[3-(4-乙基-1-哌嗪基)]丙氧基香豆素-3-羧酸1,4-丁二醇呋咱(Ⅱ11)；7-[3-(4-Ethyl-1-piperazinyl)]propoxycoumarin-3-carboxylic acid 1,4-butanediol furazan (Ⅱ 11 );

7-[3-(4-羟乙基-1-哌嗪基)]丙氧基香豆素-3-羧酸1,4-丁二醇呋咱(Ⅱ12)；7-[3-(4-Hydroxyethyl-1-piperazinyl)]propoxycoumarin-3-carboxylic acid 1,4-butanediol furazan (Ⅱ 12 );

7-(3-二乙氨基)丙氧基香豆素-3-羧酸一缩乙二醇呋咱(Ⅱ13)；7-(3-Diethylamino)propoxycoumarin-3-carboxylic acid ethylene glycol furazan (Ⅱ 13 );

7-(3-苄氨基)丙氧基香豆素-3-羧酸一缩乙二醇呋咱(Ⅱ14)；7-(3-Benzylamino)propoxycoumarin-3-carboxylic acid ethylene glycol furazan (Ⅱ 14 );

7-[3-(1-哌啶基)]丙氧基香豆素-3-羧酸一缩乙二醇呋咱(Ⅱ15)；7-[3-(1-piperidinyl)]propoxycoumarin-3-carboxylic acid ethylene glycol furazan (Ⅱ 15 );

7-[3-(1-吗啡啉基)]丙氧基香豆素-3-羧酸一缩乙二醇呋咱(Ⅱ16)；7-[3-(1-morpholinyl)]propoxycoumarin-3-carboxylic acid ethylene glycol furazan (Ⅱ 16 );

7-[3-(4-乙基-1-哌嗪基)]丙氧基香豆素-3-羧酸一缩乙二醇呋咱(Ⅱ17)；7-[3-(4-Ethyl-1-piperazinyl)]propoxycoumarin-3-carboxylic acid ethylene glycol furazan (Ⅱ 17 );

7-[3-(4-羟乙基-1-哌嗪基)]丙氧基香豆素-3-羧酸一缩乙二醇呋咱(Ⅱ18)；7-[3-(4-Hydroxyethyl-1-piperazinyl)]propoxycoumarin-3-carboxylic acid ethylene glycol furazan (Ⅱ 18 );

7-(3-二乙氨基)丙氧基香豆素-3-羧酸1,4-丁炔二醇呋咱(Ⅱ19)；7-(3-diethylamino)propoxycoumarin-3-carboxylic acid 1,4-butynediol furazan (Ⅱ 19 );

7-(3-苄氨基)丙氧基香豆素-3-羧酸1,4-丁炔二醇呋咱(Ⅱ20)；7-(3-Benzylamino)propoxycoumarin-3-carboxylic acid 1,4-butynediol furazan (Ⅱ 20 );

7-[3-(1-哌啶基)]丙氧基香豆素-3-羧酸1,4-丁炔二醇呋咱(Ⅱ21)；7-[3-(1-piperidinyl)]propoxycoumarin-3-carboxylic acid 1,4-butynediol furazan (Ⅱ 21 );

7-[3-(1-吗啡啉基)]丙氧基香豆素-3-羧酸1,4-丁炔二醇呋咱(Ⅱ22)；7-[3-(1-morpholinyl)]propoxycoumarin-3-carboxylic acid 1,4-butynediol furazan (Ⅱ 22 );

7-[3-(4-乙基-1-哌嗪基)]丙氧基香豆素-3-羧酸1,4-丁炔二醇呋咱(Ⅱ23)；7-[3-(4-Ethyl-1-piperazinyl)]propoxycoumarin-3-carboxylic acid 1,4-butynediol furazan (Ⅱ 23 );

7-[3-(4-羟乙基-1-哌嗪基)]丙氧基香豆素-3-羧酸1,4-丁炔二醇呋咱(Ⅱ24)；7-[3-(4-Hydroxyethyl-1-piperazinyl)]propoxycoumarin-3-carboxylic acid 1,4-butynediol furazan (Ⅱ 24 );

7-[3-(1-吗啡啉基)]丙氧基香豆素-3-羧酸对羟基苯乙醇呋咱(Ⅱ25)；7-[3-(1-morpholinyl)]propoxycoumarin-3-carboxylic acid p-hydroxyphenethylfurazan (Ⅱ 25 );

7-[3-(4-乙基-1-哌嗪基)]丙氧基香豆素-3-羧酸对羟基苯乙醇呋咱(Ⅱ26)；7-[3-(4-Ethyl-1-piperazinyl)]propoxycoumarin-3-carboxylic acid p-hydroxyphenethylfurazan (Ⅱ 26 );

7-[3-(4-羟乙基-1-哌嗪基)]丙氧基香豆素-3-羧酸对羟基苯乙醇呋咱(Ⅱ27)；7-[3-(4-Hydroxyethyl-1-piperazinyl)]propoxycoumarin-3-carboxylic acid p-hydroxyphenethylfurazan (Ⅱ 27 );

7-(3-二乙氨基)丙氧基香豆素-3-羧酸氨基乙醇呋咱(Ⅱ28)；7-(3-diethylamino)propoxycoumarin-3-carboxylic acid aminoethanol furazan (Ⅱ 28 );

7-(3-苯乙氨基)丙氧基香豆素-3-羧酸氨基乙醇呋咱(Ⅱ29)；7-(3-phenylethylamino)propoxycoumarin-3-carboxylic acid aminoethanol furazan (Ⅱ 29 );

7-[3-(1-吗啡啉基)]丙氧基香豆素-3-羧酸氨基乙醇呋咱(Ⅱ30)；7-[3-(1-morpholinyl)]propoxycoumarin-3-carboxylic acid aminoethanol furazan (Ⅱ 30 );

7-[3-(4-乙基-1-哌嗪基)]丙氧基香豆素-3-羧酸氨基乙醇呋咱(Ⅱ31)；7-[3-(4-Ethyl-1-piperazinyl)]propoxycoumarin-3-carboxylic acid aminoethanol furazan (Ⅱ 31 );

7-[3-(4-羟乙基-1-哌嗪基)]丙氧基香豆素-3-羧酸氨基乙醇呋咱(Ⅱ32)；7-[3-(4-Hydroxyethyl-1-piperazinyl)]propoxycoumarin-3-carboxylic acid aminoethanol furazan (Ⅱ 32 );

7-[3-(1-吗啡啉基)]丙氧基香豆素-3-羧酸氨基丙醇呋咱(Ⅱ33)；7-[3-(1-morpholinyl)]propoxycoumarin-3-carboxylic acid aminopropanol furazan (Ⅱ 33 );

7-[3-(1-哌嗪基)]丙氧基香豆素-3-羧酸氨基丙醇呋咱(Ⅱ34)；7-[3-(1-piperazinyl)]propoxycoumarin-3-carboxylic acid aminopropanol furazan (Ⅱ 34 );

7-[3-(4-乙基-1-哌嗪基)]丙氧基香豆素-3-羧酸氨基丙醇呋咱(Ⅱ35)；7-[3-(4-Ethyl-1-piperazinyl)]propoxycoumarin-3-carboxylic acid aminopropanol furazan (Ⅱ 35 );

7-[3-(4-羟乙基-1-哌嗪基)]丙氧基香豆素-3-羧酸氨基丙醇呋咱(Ⅱ36)；7-[3-(4-Hydroxyethyl-1-piperazinyl)]propoxycoumarin-3-carboxylic acid aminopropanol furazan (Ⅱ 36 );

7-[4-(1-吗啡啉基)]丁氧基香豆素-3-羧酸1,3-丙二醇呋咱(Ⅱ37)；7-[4-(1-morpholinyl)]butoxycoumarin-3-carboxylic acid 1,3-propanediol furazan (Ⅱ 37 );

7-[4-(4-乙基-1-哌嗪基)]丁氧基香豆素-3-羧酸1,3-丙二醇呋咱(Ⅱ38)；7-[4-(4-Ethyl-1-piperazinyl)]butoxycoumarin-3-carboxylic acid 1,3-propanediol furazan (Ⅱ 38 );

7-[4-(1-吗啡啉基)]丁氧基香豆素-3-羧酸1,4-丁二醇呋咱(Ⅱ39)；7-[4-(1-morpholinyl)]butoxycoumarin-3-carboxylic acid 1,4-butanediol furazan (Ⅱ 39 );

7-[4-((4-乙基)-1-哌嗪基)]丁氧基香豆素-3-羧酸1,4-丁二醇呋咱(Ⅱ40)；7-[4-((4-Ethyl)-1-piperazinyl)]butoxycoumarin-3-carboxylic acid 1,4-butanediol furazan (II 40 );

7-[4-(1-吗啡啉基)]丁氧基香豆素-3-羧酸一缩乙二醇呋咱(Ⅱ41)；7-[4-(1-morpholinyl)]butoxycoumarin-3-carboxylic acid ethylene glycol furazan (Ⅱ 41 );

7-[4-(4-乙基-1-哌嗪基)]丁氧基香豆素-3-羧酸一缩乙二醇呋咱(Ⅱ42)；7-[4-(4-Ethyl-1-piperazinyl)]butoxycoumarin-3-carboxylic acid ethylene glycol furazan (Ⅱ 42 );

7-[4-(1-吗啡啉基)]丁氧基香豆素-3-羧酸1,4-丁炔二醇呋咱(Ⅱ43)；7-[4-(1-morpholinyl)]butoxycoumarin-3-carboxylic acid 1,4-butynediol furazan (Ⅱ 43 );

7-[4-((4-乙基)-1-哌嗪基)]丁氧基香豆素-3-羧酸1,4-丁炔二醇呋咱(Ⅱ44)；7-[4-((4-Ethyl)-1-piperazinyl)]butoxycoumarin-3-carboxylic acid 1,4-butynediol furazan (II 44 );

7-[4-(1-吗啡啉基)]丁氧基香豆素-3-羧酸对羟基苯乙醇呋咱(Ⅱ45)；7-[4-(1-morpholinyl)]butoxycoumarin-3-carboxylic acid p-hydroxyphenethylfurazan (Ⅱ 45 );

7-[4-(4-乙基-1-哌嗪基)]丁氧基香豆素-3-羧酸对羟基苯乙醇呋咱(Ⅱ46)；7-[4-(4-Ethyl-1-piperazinyl)]butoxycoumarin-3-carboxylic acid p-hydroxyphenethylfurazan (Ⅱ 46 );

7-[4-(1-吗啡啉基)]丁氧基香豆素-3-羧酸氨基乙醇呋咱(Ⅱ47)；7-[4-(1-morpholinyl)]butoxycoumarin-3-carboxylic acid aminoethanol furazan (Ⅱ 47 );

7-[4-(4-乙基-1-哌嗪基)]丁氧基香豆素-3-羧酸氨基乙醇呋咱(Ⅱ48)；7-[4-(4-Ethyl-1-piperazinyl)]butoxycoumarin-3-carboxylic acid aminoethanol furazan (Ⅱ 48 );

本发明优选化合物及其与可药用酸的加合盐构成了本发明的完整部分；在可药用酸中有盐酸，氢溴酸，硫酸，磷酸，乙酸，乳酸，丙二酸，琥珀酸，富马酸，酒石酸，马来酸，柠檬酸，抗坏血酸，甲磺酸等。Preferred compounds of the invention and their addition salts with pharmaceutically acceptable acids form an integral part of the invention; among the pharmaceutically acceptable acids are hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid, acetic acid, lactic acid, malonic acid, succinic acid , fumaric acid, tartaric acid, maleic acid, citric acid, ascorbic acid, methanesulfonic acid, etc.

本发明的另一目的在于提供本发明通式I、Ⅱ所述化合物的制备方法。Another object of the present invention is to provide the preparation method of the compound described in the general formula I and II of the present invention.

通式I中所示的NO供体型香豆素衍生物通过下列方式制备：The NO donor type coumarin derivatives shown in general formula I are prepared in the following manner:

以水杨醛(1)为原料，经Knovengel反应得到香豆素-3-羧酸乙酯(2)，再经水解、酸化得香豆素-3-羧酸(3)，香豆素-3-羧酸与SOCl2反应制得相应的酰氯(4)，在三乙胺催化下，与由苯硫酚为原料制得的相应的羟烷基或氨烷基呋咱(5)反应，得到目标物(I)；合成路线如下：Using salicylaldehyde (1) as raw material, coumarin-3-carboxylic acid ethyl ester (2) was obtained by Knovengel reaction, and then hydrolyzed and acidified to obtain coumarin-3-carboxylic acid (3), coumarin-3- 3 -carboxylic acid reacts with SOCl to prepare the corresponding acid chloride (4), under the catalysis of triethylamine, reacts with the corresponding hydroxyalkyl or aminoalkylfurazan (5) prepared from thiophenol as raw material, Obtain object (I); Synthetic route is as follows:

其中，X、R的定义如前所述。Wherein, the definitions of X and R are as described above.

通式Ⅱ中所示的NO供体型香豆素衍生物通过下列方式制备：The NO donor type coumarin derivatives shown in the general formula II are prepared in the following manner:

以间二苯酚(1)为原料，经Vilsmeier-Haack反应得7-羟基苯甲醛(2)，经Knoevenagel 反应得到7-羟基香豆素-3-羧酸乙酯(3)，化合物(3)与二溴烷烃反应，得到中间体(4)。化合物(4)再与相应的胺类化合物(HR1)反应得到化合物(6)，化合物(6)经水解、酸化得到化合物(7)，在EDCI作用下，与由苯硫酚为原料制得的相应的羟烷基或氨烷基呋咱(5)反应，转化为目标物(Ⅱ)；合成路线如下：With resorcinol (1) as raw material, 7-hydroxybenzaldehyde (2) is obtained through Vilsmeier-Haack reaction, and 7-hydroxycoumarin-3-carboxylic acid ethyl ester (3) is obtained through Knoevenagel reaction, compound (3) Reaction with dibromoalkane affords intermediate (4). Compound (4) reacts with the corresponding amine compound (HR 1 ) to obtain compound (6). Compound (6) is hydrolyzed and acidified to obtain compound (7). The corresponding hydroxyalkyl or aminoalkyl furazan (5) reaction is converted into the target compound (II); the synthetic route is as follows:

其中，X、R、R1和n的定义如前所述。Wherein, X, R, R 1 and n are as defined above.

这些中间体或目标化合物均可按照常规分离技术加以纯化，并且根据需要将其转化为与可药用酸成盐。These intermediates or target compounds can be purified according to conventional separation techniques, and converted into salts with pharmaceutically acceptable acids as required.

本发明的进一步目的是提供本发明通式I、Ⅱ化合物在制备治疗肿瘤药物中的应用，尤其是治疗肝癌、乳腺癌、宫颈癌、肺癌和结肠癌药物中的应用。A further object of the present invention is to provide the application of the compounds of general formula I and II of the present invention in the preparation of drugs for treating tumors, especially the application of drugs for treating liver cancer, breast cancer, cervical cancer, lung cancer and colon cancer.

下面是本发明部分化合物的药理试验及结果：Below are the pharmacological tests and the results of some compounds of the present invention:

体外抗癌活性测试In vitro anticancer activity test

采用四甲基氮唑蓝比色法(MTT)评价本发明的化合物对7种人癌细胞株的抗增殖活性。 MTT法已广泛用于大规模的抗肿瘤药物筛选、细胞毒性试验以及肿瘤放射敏感测定等。The anti-proliferation activity of the compound of the present invention on 7 kinds of human cancer cell lines was evaluated by tetramethylazolium blue colorimetric method (MTT). MTT method has been widely used in large-scale antitumor drug screening, cytotoxicity test and tumor radiosensitivity determination.

细胞株：人肝癌细胞HepG-2、人宫颈癌细胞HeLa、人结肠癌细胞HCT116和SW620、人乳腺癌细胞MCF-7和人肺癌A549。Cell lines: human liver cancer cell HepG-2, human cervical cancer cell HeLa, human colon cancer cell HCT116 and SW620, human breast cancer cell MCF-7 and human lung cancer A549.

实验方法：将化合物用DMSO溶解，用PBS稀释至所需浓度。取处于指数生长期、生长状态良好的细胞一瓶，加入0.25％胰蛋白酶消化，使贴壁细胞脱落，制成每毫升含2×104-4×104个细胞的悬液。取细胞悬液接种于96孔板上，每孔180μL，置恒温CO2培养箱中培养24小时。换液，加入受试液，每孔20μL，培养48小时。将四甲基氮唑蓝加入96孔板中，每孔20μL，培养箱中反应4小时。吸去上清液，加入DMSO，每孔150μL，平板摇床上振摇5分钟。用酶联免疫检测仪在波长为490nm处测定每孔的吸收度，计算细胞抑制率。Experimental method: the compound was dissolved in DMSO and diluted to the desired concentration with PBS. Take a bottle of cells in exponential growth phase and in good growth state, add 0.25% trypsin to digest, make the adherent cells fall off, and make a suspension containing 2×10 4 -4×10 4 cells per ml. The cell suspension was inoculated on a 96-well plate, 180 μL per well, and cultured in a constant temperature CO 2 incubator for 24 hours. Change the medium, add the test solution, 20 μL per well, and incubate for 48 hours. Tetramethylazolium blue was added to a 96-well plate, 20 μL per well, and reacted in an incubator for 4 hours. Aspirate the supernatant, add DMSO, 150 μL per well, and shake on a plate shaker for 5 minutes. The absorbance of each well was measured at a wavelength of 490nm by an enzyme-linked immunosorbent detector, and the cell inhibition rate was calculated.

应用SPSS(Staffstical Package for the Social Science)17.0通过机率单位加权回归法(Bliss 法)计算IC50。部分实验结果如表4,表5所示。IC 50 was calculated by the probability unit weighted regression method (Bliss method) using SPSS (Staffstical Package for the Social Science) 17.0. Some experimental results are shown in Table 4 and Table 5.

表1本发明的化合物对肿瘤细胞增殖的抑制活性(10μmol/L时的抑制率，％)The compound of the present invention of table 1 is to the inhibitory activity of tumor cell proliferation (inhibition rate when 10 μ mol/L, %)

药理学数据显示，本发明涉及的NO供体型香豆素衍生物能够不同程度地抑制肿瘤细胞的增殖，且大多数化合物具有很强的抑制肿瘤细胞增殖作用。Pharmacological data show that the NO-donating coumarin derivatives involved in the present invention can inhibit the proliferation of tumor cells to varying degrees, and most of the compounds have a strong inhibitory effect on tumor cell proliferation.

具体实施方式：detailed description:

下面通过实施例具体说明本发明的内容。在本发明中，以下所述的实例是为了更好的阐述本发明，并不是用来限制本发明的范围。The content of the present invention is specifically described below by way of examples. In the present invention, the examples described below are for better illustrating the present invention, and are not intended to limit the scope of the present invention.

实施例1Example 1

香豆素-3-羧酸(3)的合成Synthesis of Coumarin-3-Carboxylic Acid (3)

在干燥的100mL圆底烧瓶中，加入4.2mL(0.04mol)水杨醛、8.5mL(0.056mol)丙二酸二乙酯、25mL无水乙醇、2滴冰醋酸和0.5mL六氢吡啶，加热回流2h。冷却后将反应物倒入水中，于冰水中结晶。抽滤得粗品香豆素-3-甲酸乙酯，重结晶得白色晶体7.5g，收率85.4％，m.p.92.0-93.0℃。In a dry 100mL round bottom flask, add 4.2mL (0.04mol) salicylaldehyde, 8.5mL (0.056mol) diethyl malonate, 25mL absolute ethanol, 2 drops of glacial acetic acid and 0.5mL hexahydropyridine, and heat Reflux for 2h. After cooling, the reactant was poured into water and crystallized in ice water. The crude ethyl coumarin-3-carboxylate was obtained by suction filtration, and 7.5 g of white crystals were obtained by recrystallization, with a yield of 85.4%, m.p.92.0-93.0°C.

在100mL圆底烧瓶中，加入25mL 95％的乙醇和NaOH溶液(8g固体NaOH溶于50mL 水中)，6g(0.028mol)香豆素-3-甲酸乙酯，加热回流15min。在搅拌下将反应混合物倒入70mL盐酸水溶液中，即析出晶体。抽滤的粗品香豆素-3-甲酸，50％乙醇重结晶，得白色晶体香豆素-3-羧酸5.2g，收率95％，m.p.193.2-194.7℃。In a 100mL round bottom flask, add 25mL of 95% ethanol and NaOH solution (8g of solid NaOH dissolved in 50mL of water), 6g (0.028mol) of ethyl coumarin-3-carboxylate, and heat to reflux for 15min. The reaction mixture was poured into 70 mL aqueous hydrochloric acid solution with stirring, and crystals were precipitated. Suction-filtered crude coumarin-3-carboxylic acid was recrystallized from 50% ethanol to obtain 5.2 g of white crystal coumarin-3-carboxylic acid, yield 95%, m.p.193.2-194.7°C.

香豆素-3-甲酰氯(4)Coumarin-3-carbonyl chloride (4)

将香豆素-3-羧酸(4g,21.0mmol)溶于15mL氯化亚砜中，滴加4滴吡啶，70℃回流搅拌6h 后，减压蒸去过量的氯化亚砜，得浅黄色固体1.8g。粗品经石油醚重结晶后得白色固体3.25g，收率82％，m.p.143.6～145.3℃。Dissolve coumarin-3-carboxylic acid (4g, 21.0mmol) in 15mL of thionyl chloride, add 4 drops of pyridine dropwise, reflux and stir at 70°C for 6h, evaporate excess thionyl chloride under reduced pressure to obtain shallow Yellow solid 1.8 g. The crude product was recrystallized from petroleum ether to obtain 3.25 g of a white solid, with a yield of 82%, m.p.143.6-145.3°C.

1,4-丁炔二醇呋咱(5)的合成Synthesis of 1,4-Butynediol Furazan (5)

将苯硫酚(12.1g,0.11mol)，氢氧化钠(4.4g,0.11mol)溶于50mL95％乙醇中，加入由氯乙酸(11.4g,0.12mol)和碳酸钠(6.35g，0.06mol)配成的100mL水溶液，室温搅拌3h，回流1 h。冷却至室温后加入6mol/L盐酸调pH＝2,减压蒸去乙醇，有白色沉淀生成，过滤，得16.4 g白色棒状晶体2-苯硫基乙酸，收率89％，mp：60.1～62.0℃。Thiophenol (12.1g, 0.11mol), sodium hydroxide (4.4g, 0.11mol) were dissolved in 50mL95% ethanol, and chloroacetic acid (11.4g, 0.12mol) and sodium carbonate (6.35g, 0.06mol) were added Dubbed 100mL aqueous solution, stirred at room temperature for 3h, and refluxed for 1h. After cooling to room temperature, add 6mol/L hydrochloric acid to adjust the pH to 2, distill off the ethanol under reduced pressure, a white precipitate is formed, filter to obtain 16.4 g of white rod-shaped crystals of 2-phenylthioacetic acid, the yield is 89%, mp: 60.1～62.0 ℃.

将2-苯硫基乙酸(16.0g,0.1mol)溶于65mL冰醋酸中，加入30％的过氧化氢(20mL，0.2 mol)，室温搅拌2.5h，得无色澄清溶液，滴加95％的发烟硝酸(40mL,0.9mol)升温至90℃反应 30min，冷却至室温,有白色针状晶体3，4-二苯磺酰基-1，2，5-噁二唑-2-氧化物析出，过滤干燥得14g，两步收率76％,mp：154.2～156.0℃。Dissolve 2-phenylthioacetic acid (16.0g, 0.1mol) in 65mL of glacial acetic acid, add 30% hydrogen peroxide (20mL, 0.2mol), stir at room temperature for 2.5h to obtain a colorless and clear solution, add dropwise 95% Fuming nitric acid (40mL, 0.9mol) was heated to 90°C for 30min, cooled to room temperature, white needle-like crystals of 3,4-diphenylsulfonyl-1,2,5-oxadiazole-2-oxide were precipitated , filtered and dried to obtain 14g, two-step yield 76%, mp: 154.2～156.0℃.

将呋咱(1g,2.7mmol)、1,4-丁炔二醇(0.86g,10.0mmol)溶于10ml四氢呋喃中，冰浴下缓慢滴加25％氢氧化钠水溶液(0.5mL,3.0mmol)，冰浴搅拌，TLC跟踪。约30mim后TLC(EA:PE＝1:2, V:V)显示反应已基本完全，加入100mL水，乙酸乙酯萃取(4*30mL)，有机相合并后用饱和氯化钠溶液洗涤1次，无水硫酸钠干燥2h。浓缩，柱层析(流动相为DCM:PE＝2:1,V:V)，浓缩，得白色固体0.54g，收率69％，m.p.116.1～118.0℃。Furazan (1g, 2.7mmol) and 1,4-butynediol (0.86g, 10.0mmol) were dissolved in 10ml of tetrahydrofuran, and 25% aqueous sodium hydroxide solution (0.5mL, 3.0mmol) was slowly added dropwise under ice-cooling , stirring in an ice bath, followed by TLC. After about 30mim, TLC (EA:PE=1:2, V:V) shows that the reaction is almost complete, add 100mL water, extract with ethyl acetate (4*30mL), combine the organic phases and wash once with saturated sodium chloride solution , dried over anhydrous sodium sulfate for 2h. Concentration, column chromatography (mobile phase: DCM:PE = 2:1, V:V), concentration gave 0.54 g of white solid, yield 69%, m.p.116.1-118.0°C.

香豆素-3-羧酸-1,4-丁炔二醇呋咱(I4)的合成Synthesis of Coumarin-3-Carboxylic Acid-1,4-Butynediol Furazan (I 4 )

将1,4-丁炔二醇呋咱(310mg,1.0mmol)、三乙胺(0.83mL,6.0mmol)溶于20mL DCM中，在冰盐浴中缓慢滴加香豆素-3-甲酰氯(312mg,1.5mmol)的二氯甲烷溶液，滴毕转至室温搅拌， TLC跟踪反应进程。约2h后TLC(EA:PE＝1:2,V:V)显示反应基本完全，加水100mL，DCM 萃取(3*20mL)，有机相合并后用饱和氯化钠溶液萃取1次，无水硫酸钠干燥2h，浓缩至干。柱层析(流动相为EA:PE＝1:4，V:V)，减压蒸去流动相，得白色固体380mg，收率79％，m.p. 135.1～138.1℃；ES-MS(m/z):505.1[M+Na]+；IR(KBr,cm-1):2914.23,1762.89,1609.79, 1556.82；1H NMR(400MHz,CDCl3)δ：8.64(s,1H),8.10(s,2H),7.79(s,1H),7.68(s,4H), 7.40(s,2H),5.16(s,2H),5.04(s,2H)；Dissolve 1,4-butynediol furazan (310mg, 1.0mmol) and triethylamine (0.83mL, 6.0mmol) in 20mL DCM, slowly add coumarin-3-formyl chloride dropwise in an ice-salt bath (312mg, 1.5mmol) in dichloromethane solution, after the dropwise transfer to room temperature to stir, TLC tracking the reaction progress. After about 2 hours, TLC (EA:PE=1:2, V:V) showed that the reaction was almost complete. Add 100mL of water, extract with DCM (3*20mL), combine the organic phases and extract once with saturated sodium chloride solution, and anhydrous sulfuric acid Sodium drying 2h, concentrated to dryness. Column chromatography (mobile phase is EA:PE=1:4, V:V), and the mobile phase was evaporated under reduced pressure to obtain 380 mg of white solid, yield 79%, mp 135.1～138.1°C; ES-MS (m/z ):505.1[M+Na] + ; IR(KBr,cm -1 ):2914.23, 1762.89, 1609.79, 1556.82; 1 H NMR(400MHz, CDCl 3 )δ: 8.64(s,1H), 8.10(s,2H ),7.79(s,1H),7.68(s,4H), 7.40(s,2H),5.16(s,2H),5.04(s,2H);

实施例2Example 2

参照实施例1的方法，制备香豆素-3-甲酰氯及3,4-二苯磺酰基-1,2,5-噁二唑-2-氧化物。Referring to the method of Example 1, coumarin-3-formyl chloride and 3,4-diphenylsulfonyl-1,2,5-oxadiazole-2-oxide were prepared.

氨基乙醇呋咱(5)的制备Preparation of Aminoethanol Furazan (5)

将NaH(142mg,5.9mmol)、氨基乙醇(0.2ml,3.33mmol)加入50ml圆底烧瓶中，避光、冰盐浴搅拌滴加已溶于THF的呋咱，即3,4-二苯磺酰基-1,2,5-噁二唑-2-氧化物 (0.5g,1.37mmol)，保持冰浴反应。TLC检测至反应完全。向反应液中加入水，EtOAc萃取后，有机层用饱和NaCl洗，TLC检测有机层点较单一。无水Na2SO4干燥后，减压浓缩至干，称重 239mg。收率62％。Add NaH (142mg, 5.9mmol) and aminoethanol (0.2ml, 3.33mmol) into a 50ml round bottom flask, keep away from light, stir in an ice-salt bath, add furazan dissolved in THF, that is, 3,4-dibenzenesulfonate Acyl-1,2,5-oxadiazole-2-oxide (0.5g, 1.37mmol), keep the reaction on ice bath. TLC detected that the reaction was complete. Water was added to the reaction solution, and after extraction with EtOAc, the organic layer was washed with saturated NaCl, and TLC detected that the organic layer had a single spot. After drying over anhydrous Na 2 SO 4 , it was concentrated to dryness under reduced pressure and weighed 239 mg. Yield 62%.

香豆素-3-羧酸-乙醇胺呋咱(I6)的合成Synthesis of Coumarin-3-Carboxylic Acid-Ethanolamine Furazan (I 6 )

将乙醇胺呋咱(285mg,1.0mmol)、三乙胺(0.83ml,6.0mmol)溶于20mL DCM中，在冰盐浴中缓慢滴加香豆素-3-甲酰氯(312mg,1.2mmol)的DCM溶液，滴毕转至室温搅拌，TLC跟踪反应进程。约2h后TLC(MeOH:DCM＝1:20,V:V)显示反应基本完全，加水100mL，DCM 萃取(3*20mL)，有机相合并后用饱和氯化钠溶液萃取1次，无水硫酸钠干燥2h，浓缩至干。柱层析，流动相为MeOH:DCM＝1:30，减压蒸去流动相，得浅黄色固体320mg，收率68％，m.p.142.3～145.7℃。ES-MS(m/z):498.3[M+Na]+；IR(KBr,cm-1)3273.41,3022.18,2924.72, 1710.34,1650.40,1632.58；1H NMR(400MHz,CDCl3)δ9.05(s,1H),9.00(s,1H),8.07(d,J＝ 6.0Hz,2H),7.74-7.63(m,5H),7.42(d,J＝7.0Hz,2H),4.55(s,2H),3.70(s,2H).Dissolve ethanolamine furazan (285mg, 1.0mmol) and triethylamine (0.83ml, 6.0mmol) in 20mL DCM, and slowly add coumarin-3-formyl chloride (312mg, 1.2mmol) dropwise in an ice-salt bath The DCM solution was stirred at room temperature after dropping, and the reaction progress was tracked by TLC. After about 2 hours, TLC (MeOH:DCM=1:20, V:V) showed that the reaction was almost complete. Add 100mL of water, extract with DCM (3*20mL), combine the organic phases and extract once with saturated sodium chloride solution, and anhydrous sulfuric acid Sodium drying 2h, concentrated to dryness. Column chromatography, the mobile phase was MeOH:DCM=1:30, the mobile phase was evaporated under reduced pressure to obtain 320 mg of light yellow solid, the yield was 68%, and the mp was 142.3-145.7°C. ES-MS (m/z): 498.3[M+Na] + ; IR (KBr, cm -1 ) 3273.41, 3022.18, 2924.72, 1710.34, 1650.40, 1632.58; 1 H NMR (400MHz, CDCl 3 ) δ9.05( s,1H),9.00(s,1H),8.07(d,J＝6.0Hz,2H),7.74-7.63(m,5H),7.42(d,J＝7.0Hz,2H),4.55(s,2H ),3.70(s,2H).

实施例3Example 3

参照实施例1合成1,4-丁炔二醇呋咱。Referring to Example 1, 1,4-butynediol furoxan was synthesized.

2,4-二羟基苯甲醛的合成Synthesis of 2,4-Dihydroxybenzaldehyde

在500mL三口烧瓶中加入DMF(19mL,210mmol)和乙腈(100mL)，室温下充分搅拌。在冰浴条件下缓慢滴加三氯氧磷(19mL,250mmol)，1h滴加完毕，再在室温下搅拌1h。将1,3-苯二酚(21g,190mmol)溶于乙腈中，再缓慢滴加到反应溶液中，有白色沉淀生成，滴加完毕后溶液在冰浴下搅拌4h，室温下搅拌2h。抽滤，用冰丙酮洗涤滤饼，所得固体在50℃中真空干燥至衡重。将固体转移至500mL圆底烧瓶中，加入400mL水，50℃加热搅拌30min，再室温搅拌2h，有粉红色针状固体析出。粗品经硫代硫酸钠脱色，50％乙醇重结晶后得白色针状晶体18.5g，收率70.2％，m.p.134.2～135.8℃。Add DMF (19mL, 210mmol) and acetonitrile (100mL) into a 500mL three-necked flask, and stir well at room temperature. Phosphorus oxychloride (19 mL, 250 mmol) was slowly added dropwise in an ice bath, and the addition was completed after 1 h, and then stirred at room temperature for 1 h. Dissolve 1,3-benzenediol (21g, 190mmol) in acetonitrile, and slowly add it dropwise to the reaction solution, a white precipitate is formed. After the dropwise addition, the solution is stirred for 4 hours in an ice bath and 2 hours at room temperature. Filter with suction, wash the filter cake with ice acetone, and vacuum-dry the obtained solid at 50°C to constant weight. Transfer the solid to a 500mL round bottom flask, add 400mL of water, heat and stir at 50°C for 30min, then stir at room temperature for 2h, a pink needle-like solid precipitates. The crude product was decolorized by sodium thiosulfate and recrystallized from 50% ethanol to obtain 18.5 g of white needle-like crystals, yield 70.2%, m.p.134.2-135.8°C.

7-羟基香豆素-3-甲酸乙酯的合成Synthesis of Ethyl 7-Hydroxycoumarin-3-carboxylate

在250mL圆底烧瓶中加入2,4-二羟基苯甲醛(10g,72.5mmol)及30mL无水乙醇，搅拌使之充分溶解。加入丙二酸二乙酯(17.2mL,101.9mmol)、六氢吡啶(0.57mL,5.76mmol)、冰乙酸(0.16mL,2.88mmol)，90℃加热搅拌，TLC跟踪反应进程。约15h后TLC(EA：PE＝1:2)显示反应基本完全。将反应液降至室温，加入200mL冰水，于-20℃下放置过夜。抽滤，得黄色固体12.4g，收率73％。粗品用95％乙醇重结晶，得浅黄色针状固体10.8g，收率64％，m.p.191.7～192.5℃。Add 2,4-dihydroxybenzaldehyde (10 g, 72.5 mmol) and 30 mL of absolute ethanol into a 250 mL round-bottomed flask, and stir to fully dissolve it. Add diethyl malonate (17.2mL, 101.9mmol), hexahydropyridine (0.57mL, 5.76mmol), glacial acetic acid (0.16mL, 2.88mmol), heat and stir at 90°C, and track the reaction progress by TLC. After about 15 h, TLC (EA:PE=1:2) showed that the reaction was almost complete. The reaction solution was cooled down to room temperature, 200 mL of ice water was added, and left overnight at -20°C. After suction filtration, 12.4 g of a yellow solid was obtained, with a yield of 73%. The crude product was recrystallized with 95% ethanol to obtain 10.8 g of light yellow needle-like solid, yield 64%, m.p.191.7-192.5°C.

7-(3-溴丙氧基)香豆素-3-甲酸乙酯的合成Synthesis of Ethyl 7-(3-Bromopropoxy)coumarin-3-carboxylate

将7-羟基香豆素-3-甲酸乙酯(2g,8.55mmol)、无水碳酸钾(1.77g,12.8mmol)溶于20mL DMF中，75℃下搅拌30min。加入1,3-二溴丙烷(2.6mL,25.6mmol)，继续于75℃下搅拌反应，TLC跟踪反应进程。约30min后TLC(EA:PE＝1:2,V:V)显示反应基本完全。冷却至室温，加入DCM 200mL，用水洗涤(5*30mL)，有机相用饱和氯化钠溶液洗涤1次，无水硫酸钠干燥2h。减压浓缩至干，柱层析(流动相为EA:PE＝1:4,V:V)。减压蒸去溶剂，得白色固体2.53g，收率81％，m.p.152.3～152.9℃Dissolve ethyl 7-hydroxycoumarin-3-carboxylate (2g, 8.55mmol) and anhydrous potassium carbonate (1.77g, 12.8mmol) in 20mL DMF, and stir at 75°C for 30min. Add 1,3-dibromopropane (2.6mL, 25.6mmol), continue to stir the reaction at 75°C, and follow the progress of the reaction by TLC. After about 30 min, TLC (EA:PE=1:2, V:V) showed that the reaction was almost complete. Cool to room temperature, add 200 mL of DCM, wash with water (5*30 mL), wash the organic phase once with saturated sodium chloride solution, and dry over anhydrous sodium sulfate for 2 h. Concentrate to dryness under reduced pressure, and perform column chromatography (mobile phase is EA:PE=1:4, V:V). The solvent was distilled off under reduced pressure to obtain 2.53 g of white solid, yield 81%, m.p.152.3～152.9°C

7-[(3-吗啉-1基)丙氧基]香豆素-3-甲酸的合成Synthesis of 7-[(3-morpholin-1 yl)propoxy]coumarin-3-carboxylic acid

将7-(3-溴丙氧基)香豆素-3-甲酸乙酯(354mg,1.0mmol)、无水碳酸钾(276mg,2.0mmol)、吗啉(0.26mL,3.0mmol)溶于10mL DMF中，85℃回流搅拌，TLC跟踪反应进程。约1h后 TLC(MeOH：DCM＝1:30,V:V)显示反应基本完全，将反应混合物倾入100mL DCM中，用水洗涤(4*30mL)，有机相合并后用饱和氯化钠溶液洗涤1次，无水硫酸钠干燥2h，减压浓缩至干。柱层析(流动相为EA:PE＝1:1,V:V)。减压蒸去溶剂，得浅黄色固体260mg，收率72％。将产物在30％NaOH的乙醇溶液中水解30min，再经6mmol/L盐酸酸化，减压蒸干溶剂，加丙酮溶解、过滤，得黄色固体210mg，粗品不经纯化直接投入后续反应中。Dissolve ethyl 7-(3-bromopropoxy)coumarin-3-carboxylate (354mg, 1.0mmol), anhydrous potassium carbonate (276mg, 2.0mmol), morpholine (0.26mL, 3.0mmol) in 10mL In DMF, stir under reflux at 85°C, and follow the progress of the reaction by TLC. After about 1h, TLC (MeOH:DCM=1:30, V:V) showed that the reaction was almost complete, the reaction mixture was poured into 100mL DCM, washed with water (4*30mL), the organic phase was combined and washed with saturated sodium chloride solution 1 time, dried over anhydrous sodium sulfate for 2h, and concentrated to dryness under reduced pressure. Column chromatography (mobile phase is EA:PE=1:1, V:V). The solvent was distilled off under reduced pressure to obtain 260 mg of light yellow solid with a yield of 72%. The product was hydrolyzed in 30% NaOH ethanol solution for 30 min, then acidified with 6 mmol/L hydrochloric acid, evaporated to dryness under reduced pressure, dissolved in acetone, and filtered to obtain 210 mg of a yellow solid, which was directly put into the subsequent reaction without purification.

7-[(3-吗啉-1-基)丙氧基]香豆素-3-羧酸1,4-丁炔二醇呋咱(Ⅱ22)7-[(3-morpholin-1-yl)propoxy]coumarin-3-carboxylic acid 1,4-butynediol furazan (Ⅱ 22 )

将7-[(3-吗啉-1-基)丙氧基]香豆素-3-甲酸(330mg,0.10mmol)、1,4-丁炔二醇呋咱 (460mg,0.15mmol)、DMAP(60mg,0.05mmol)、TBAB(320mg,0.10mmol)溶于10mL DCM中，于冰浴下缓慢滴加EDCI(190mg,0.10mmol)的DCM溶液，滴毕转至室温搅拌，TLC跟踪反应进程。24小时后TLC(EA:PE＝1:1,V:V)显示反应基本完全。停止搅拌，将反应液倾入100ml 水中，DCM萃取(3*20mL)，有机相合并后用饱和氯化钠溶液洗涤1次，减压浓缩。柱层析(流动相为EA:PE＝1:1,V:V)，减压蒸去溶剂，得黄色固体385mg，收率62％。ES-MS(m/z): 626.6[M+H]+；IR(KBr,cm-1):3512.33,2936.21,1760.60,1629.26,1555.59；1H NMR(400MHz, CDCl3)δ8.61(d,J＝21.3Hz,1H),8.09(d,J＝2.5Hz,2H),7.78(d,J＝2.7Hz,1H),7.66(s,2H), 7.55(s,1H),6.91(d,J＝4.4Hz,1H),6.81(s,1H),5.14(s,2H),5.00(s,2H),4.08(s,2H),3.74(s, 4H),2.48(s,4H),2.40(s,2H),1.87(s,2H),1.59(s,2H),1.53(s,2H).7-[(3-morpholin-1-yl)propoxy]coumarin-3-carboxylic acid (330mg, 0.10mmol), 1,4-butynediol furazan (460mg, 0.15mmol), DMAP (60mg, 0.05mmol) and TBAB (320mg, 0.10mmol) were dissolved in 10mL of DCM, and the DCM solution of EDCI (190mg, 0.10mmol) was slowly added dropwise under an ice bath, and stirred at room temperature after dropping, followed by TLC. After 24 hours TLC (EA:PE=1:1, V:V) showed that the reaction was almost complete. Stirring was stopped, the reaction solution was poured into 100ml of water, extracted with DCM (3*20mL), the organic phases were combined, washed once with saturated sodium chloride solution, and concentrated under reduced pressure. After column chromatography (mobile phase: EA:PE=1:1, V:V), the solvent was evaporated under reduced pressure to obtain 385 mg of a yellow solid with a yield of 62%. ES-MS(m/z): 626.6[M+H] + ; IR(KBr,cm -1 ):3512.33,2936.21,1760.60,1629.26,1555.59; 1 H NMR(400MHz, CDCl3)δ8.61(d, J＝21.3Hz, 1H), 8.09(d, J＝2.5Hz, 2H), 7.78(d, J＝2.7Hz, 1H), 7.66(s, 2H), 7.55(s, 1H), 6.91(d, J＝4.4Hz,1H),6.81(s,1H),5.14(s,2H),5.00(s,2H),4.08(s,2H),3.74(s,4H),2.48(s,4H), 2.40(s,2H),1.87(s,2H),1.59(s,2H),1.53(s,2H).

实施例4Example 4

参照实施例1合成1,4-丁炔二醇呋咱，参照实施例3合成7-羟基香豆素-3-甲酸乙酯。1,4-butynediol furazan was synthesized with reference to Example 1, and ethyl 7-hydroxycoumarin-3-carboxylate was synthesized with reference to Example 3.

7-(4-溴丁氧基)香豆素-3-甲酸乙酯的合成Synthesis of Ethyl 7-(4-Bromobutoxy)coumarin-3-carboxylate

将7-羟基香豆素-3-甲酸乙酯(2g,8.55mmol)、无水碳酸钾(1.77g,12.8mmol)溶于20mL DMF中，75℃下搅拌30min。加入1,4-二溴丁烷(3.06mL,25.6mmol)，继续于75℃下搅拌反应，TLC跟踪反应进程。约30min后TLC(EA:PE＝1:2,V:V)显示反应基本完全。冷却至室温，加入DCM 200mL，用水洗涤(5*30mL)，有机相用饱和氯化钠溶液洗涤1次，无水硫酸钠干燥2h。减压浓缩至干，柱层析(流动相为EA:PE＝1:4)。减压蒸去溶剂，得白色固体2.6g，收率81％，m.p.140.6～141.0℃。Dissolve ethyl 7-hydroxycoumarin-3-carboxylate (2g, 8.55mmol) and anhydrous potassium carbonate (1.77g, 12.8mmol) in 20mL DMF, and stir at 75°C for 30min. Add 1,4-dibromobutane (3.06mL, 25.6mmol), continue to stir the reaction at 75°C, and track the reaction progress by TLC. After about 30 min, TLC (EA:PE=1:2, V:V) showed that the reaction was almost complete. Cool to room temperature, add 200 mL of DCM, wash with water (5*30 mL), wash the organic phase once with saturated sodium chloride solution, and dry over anhydrous sodium sulfate for 2 h. Concentrate to dryness under reduced pressure, and perform column chromatography (mobile phase is EA:PE=1:4). The solvent was distilled off under reduced pressure to obtain 2.6 g of white solid, yield 81%, m.p.140.6-141.0°C.

7-[4-(4-乙基-1-哌嗪基)]丁氧基香豆素-3-羧酸的合成Synthesis of 7-[4-(4-ethyl-1-piperazinyl)]butoxycoumarin-3-carboxylic acid

将香豆素-C4-溴代中间体(369mg,0.1mmol)、无水碳酸钾(276mg,2.0mmol)溶于10mL DMF中，加入N-乙基哌嗪(0.52mL,3.0mmol)，50℃搅拌，TLC跟踪反应进程。约1h后 TLC(MeOH:DCM＝1:20)显示反应基本完全，将反应混合物倾入100mL水中，DCM萃取 (3*40mL)，有机相合并后用饱和氯化钠溶液洗涤1次，无水硫酸钠干燥2h，减压浓缩至干。柱层析(流动相为MeOH:DCM＝1:20)。减压蒸去溶剂，得黄色油状物284mg，收率71％。将产物在30％NaOH的乙醇溶液中水解30min，再经6mmol/L盐酸酸化，减压蒸干溶剂，加丙酮溶解、过滤，得黄色固体210mg，粗品不经纯化直接投入后续反应中。Dissolve coumarin-C4-bromo intermediate (369mg, 0.1mmol), anhydrous potassium carbonate (276mg, 2.0mmol) in 10mL DMF, add N-ethylpiperazine (0.52mL, 3.0mmol), 50 ℃ stirring, TLC tracking reaction progress. After about 1h, TLC (MeOH:DCM=1:20) showed that the reaction was almost complete. The reaction mixture was poured into 100mL water, extracted with DCM (3*40mL), the organic phases were combined, washed once with saturated sodium chloride solution, and anhydrous Dry over sodium sulfate for 2h, and concentrate to dryness under reduced pressure. Column chromatography (mobile phase is MeOH:DCM=1:20). The solvent was distilled off under reduced pressure to obtain 284 mg of a yellow oily substance, with a yield of 71%. The product was hydrolyzed in 30% NaOH ethanol solution for 30 min, then acidified with 6 mmol/L hydrochloric acid, evaporated to dryness under reduced pressure, dissolved in acetone, and filtered to obtain 210 mg of a yellow solid, which was directly put into the subsequent reaction without purification.

7-[4-(4-乙基-1-哌嗪基)]丁氧基香豆素-3-羧酸1,4-丁炔二醇呋咱(Ⅱ44)的合成Synthesis of 7-[4-(4-ethyl-1-piperazinyl)]butoxycoumarin-3-carboxylic acid 1,4-butynediol furazan (Ⅱ 44 )

将7-[4-(4-乙基-1-哌嗪基)]丁氧基香豆素-3-羧酸(370mg,0.10mmol)、1,4-丁炔二醇呋咱 (460mg,0.15mmol)、DMAP(60mg,0.05mmol)、TBAB(320mg,0.10mmol)溶于10mLDCM中，于冰浴下缓慢滴加EDCI(190mg,0.10mmol)的DCM溶液，滴毕转至室温搅拌，TLC跟踪反应进程。24小时后TLC(MeOH:DCM＝1:10,V:V)显示反应基本完全。停止搅拌，将反应液倾入100ml水中，DCM萃取(3*20mL)，有机相合并后用饱和氯化钠溶液洗涤1次，减压浓缩。柱层析(流动相为MeOH:DCM＝1:20,V:V)，减压蒸去溶剂，得黄色固体430mg，收率65％。7-[4-(4-Ethyl-1-piperazinyl)]butoxycoumarin-3-carboxylic acid (370mg, 0.10mmol), 1,4-butynediol furazan (460mg, 0.15mmol), DMAP (60mg, 0.05mmol), and TBAB (320mg, 0.10mmol) were dissolved in 10mL DCM, and slowly added dropwise a DCM solution of EDCI (190mg, 0.10mmol) in an ice bath. Track reaction progress. After 24 hours TLC (MeOH:DCM=1:10, V:V) showed that the reaction was almost complete. Stirring was stopped, the reaction solution was poured into 100ml of water, extracted with DCM (3*20mL), the organic phases were combined, washed once with saturated sodium chloride solution, and concentrated under reduced pressure. After column chromatography (mobile phase: MeOH:DCM=1:20, V:V), the solvent was evaporated under reduced pressure to obtain 430 mg of a yellow solid with a yield of 65%.

ES-MS(m/z):667.7[M+H]+；IR(KBr,cm-1)3523.18,3064.77,1750.15,1694.57,1620.86, 1563.35；1H NMR(400MHz,DMSO-d6)δ8.84(s,1H),7.92(s,2H),7.60(s,1H),7.48(s,1H), 7.32(s,1H),7.06(s,2H),5.08(s,1H),4.14(s,2H),3.50(s,4H),3.18(s,3H),3.06(s,1H),2.84(s, 2H),2.71(s,2H),1.76(s,2H),1.58(s,3H),1.31(s,2H),1.19(s,2H),0.94(s,3H).ES-MS (m/z): 667.7[M+H] + ; IR (KBr, cm -1 ) 3523.18, 3064.77, 1750.15, 1694.57, 1620.86, 1563.35; 1 H NMR (400MHz, DMSO-d 6 ) δ8. 84(s,1H),7.92(s,2H),7.60(s,1H),7.48(s,1H), 7.32(s,1H),7.06(s,2H),5.08(s,1H),4.14 (s,2H),3.50(s,4H),3.18(s,3H),3.06(s,1H),2.84(s,2H),2.71(s,2H),1.76(s,2H),1.58( s,3H),1.31(s,2H),1.19(s,2H),0.94(s,3H).

Claims (10)

1.通式I所示的NO供体型香豆素衍生物：1. NO donor type coumarin derivatives shown in general formula I: 其中：in: X代表-O-或-NH-；X stands for -O- or -NH-; R代表-(CH2)n-，其中n＝1～6、-CH(CH3)CH2-、-CH(CH3)(CH2)2-、-(CH2)2O(CH2)2-、-Ph(CH2)2-、-(CH2)2NH(CH2)2-、-CH2CH＝CHCH2-或-CH2C≡CCH2-。R represents -(CH 2 )n-, where n=1~6, -CH(CH 3 )CH 2 -, -CH(CH 3 )(CH 2 ) 2 -, -(CH 2 ) 2 O(CH 2 ) 2 -, -Ph(CH 2 ) 2 -, -(CH 2 ) 2 NH(CH 2 ) 2 -, -CH 2 CH═CHCH 2 - or -CH 2 C≡CCH 2 -. 2.通式II所示的NO供体型香豆素衍生物或其药学上可接受的盐：2. NO-donating coumarin derivatives represented by general formula II or pharmaceutically acceptable salts thereof: 其中：in: n＝1～6；n=1～6; X为-O-或-NH-；X is -O- or -NH-; R代表-(CH2)n-，其中n＝1～6、-CH(CH3)CH2-、-CH(CH3)(CH2)2-、-(CH2)2O(CH2)2-、-Ph(CH2)2-、-(CH2)2NH(CH2)2-、-CH2CH＝CHCH2-或-CH2C≡CCH2-；R represents -(CH 2 )n-, where n=1~6, -CH(CH 3 )CH 2 -, -CH(CH 3 )(CH 2 ) 2 -, -(CH 2 ) 2 O(CH 2 ) 2 -, -Ph(CH 2 ) 2 -, -(CH 2 ) 2 NH(CH 2 ) 2 -, -CH 2 CH=CHCH 2 - or -CH 2 C≡CCH 2 -; R1代表NR1R2；R 1 represents NR 1 R 2 ; R1和R2可相同或不同，并且彼此独立地代表氢原子、C1-C6烷基、苯基、苄基、苯乙基或R1和R2与其所连接的氮原子一起形成五至七元脂肪杂环或芳杂环，该环基可任意地由下述相同或不同的取代基单取代至五取代，所述取代基包括：C1-C6烷基、C1-C6烷氧基、羟基或羟基-(C1-C6)烷基。R 1 and R 2 may be the same or different, and independently of each other represent a hydrogen atom, C 1 -C 6 alkyl, phenyl, benzyl, phenethyl or R 1 and R 2 together with the nitrogen atom to which they are attached form a five to a seven-membered aliphatic heterocyclic ring or aromatic heterocyclic ring, the ring group can be optionally substituted by the following substituents of the same or different substituents, the substituents include: C 1 -C 6 alkyl, C 1 -C 6Alkoxy , hydroxy or hydroxy-(C 1 -C 6 )alkyl. 3.根据权利要求1所述的通式I化合物，其特征在于：3. the compound of general formula I according to claim 1, characterized in that: X为-O-或-NH-；R代表-(CH2)n-，其中n＝2～6、-CH(CH3)CH2-、-CH(CH3)(CH2)2-、-(CH2)2O(CH2)2-、-Ph(CH2)2-、-CH2CH＝CHCH2-或-CH2C≡CCH2-。X is -O- or -NH-; R represents -(CH 2 )n-, where n=2~6, -CH(CH 3 )CH 2 -, -CH(CH 3 )(CH 2 ) 2 -, -(CH 2 ) 2 O(CH 2 ) 2 -, -Ph(CH 2 ) 2 -, -CH 2 CH═CHCH 2 - or -CH 2 C≡CCH 2 -. 4.根据权利要求2所述的通式Ⅱ化合物或其药学上可接受的盐，其特征在于：4. The compound of general formula II or a pharmaceutically acceptable salt thereof according to claim 2, characterized in that: n＝2～6；X为-O-或-NH-；R代表-(CH2)n-，其中n＝2～6、-CH(CH3)CH2-、-CH(CH3)(CH2)2-、-(CH2)2O(CH2)2-、-Ph(CH2)2-、-CH2CH＝CHCH2-或-CH2C≡CCH2-；R1代表氨基、二甲胺基、二乙胺基、二丙胺基、二正丁胺基、苯胺基、苄胺基、苯乙胺基、吡咯基、哌啶基、吗啡啉基、咪唑基、哌嗪基、4-甲基哌啶基、N-甲基哌嗪基、N-乙基哌嗪基或4-羟乙基哌嗪基。n=2~6; X is -O- or -NH-; R represents -(CH 2 )n-, where n=2~6, -CH(CH 3 )CH 2 -, -CH(CH 3 )( CH 2 ) 2 -, -(CH 2 ) 2 O(CH 2 ) 2 -, -Ph(CH 2 ) 2 -, -CH 2 CH=CHCH 2 - or -CH 2 C≡CCH 2 -; R 1 represents Amino, dimethylamino, diethylamino, dipropylamino, di-n-butylamino, anilino, benzylamino, phenethylamino, pyrrolyl, piperidinyl, morpholinyl, imidazolyl, piperazine , 4-methylpiperidinyl, N-methylpiperazinyl, N-ethylpiperazinyl or 4-hydroxyethylpiperazinyl. 5.根据权利要求1所述的通式I化合物，其特征在于：5. the compound of general formula I according to claim 1, characterized in that: X代表-O-或-NH-；R代表-(CH2)n-，其中n＝2～6、-CH(CH3)CH2-、-CH(CH3)(CH2)2-、-(CH2)2O(CH2)2-、-Ph(CH2)2-或-CH2C≡CCH2-。X represents -O- or -NH-; R represents -(CH 2 )n-, where n=2~6, -CH(CH 3 )CH 2 -, -CH(CH 3 )(CH 2 ) 2 -, -(CH 2 ) 2 O(CH 2 ) 2 -, -Ph(CH 2 ) 2 - or -CH 2 C≡CCH 2 -. 6.根据权利要求2所述的通式Ⅱ化合物或其药学上可接受的盐，其特征在于：6. The compound of general formula II or a pharmaceutically acceptable salt thereof according to claim 2, characterized in that: n＝2～4；X代表-O-或-NH-；R代表-(CH2)n-，其中n＝2～6、-CH(CH3)CH2-、-CH(CH3)(CH2)2-、-(CH2)2O(CH2)2-、-Ph(CH2)2-或-CH2C≡CCH2-；R1代表氨基、二甲胺基、二乙胺基、苯胺基、苄胺基、苯乙胺基、哌啶基、吗啡啉基、哌嗪基、N-甲基哌嗪基、N-乙基哌嗪基或4-羟乙基哌嗪基。n=2～4; X represents -O- or -NH-; R represents -(CH 2 )n-, wherein n=2～6, -CH(CH 3 )CH 2 -, -CH(CH 3 )( CH 2 ) 2 -, -(CH 2 ) 2 O(CH 2 ) 2 -, -Ph(CH 2 ) 2 - or -CH 2 C≡CCH 2 -; R 1 represents amino, dimethylamino, diethyl Amine, anilino, benzylamino, phenethylamino, piperidinyl, morpholinyl, piperazinyl, N-methylpiperazinyl, N-ethylpiperazinyl or 4-hydroxyethylpiperazine base. 7.权利要求1所述的通式I化合物的制备方法，其特征在于：7. the preparation method of general formula I compound described in claim 1 is characterized in that: 以水杨醛(1)为原料，经Knovengel反应得到香豆素-3-羧酸乙酯(2)，再经水解、酸化得香豆素-3-羧酸(3)，香豆素-3-羧酸与SOCl2反应制得相应的酰氯(4)，在三乙胺催化下，与由苯硫酚为原料制得的相应的羟烷基或氨烷基呋咱(5)反应，得到目标物(I)；合成路线如下：Using salicylaldehyde (1) as raw material, coumarin-3-carboxylic acid ethyl ester (2) was obtained by Knovengel reaction, and then hydrolyzed and acidified to obtain coumarin-3-carboxylic acid (3), coumarin-3- 3 -carboxylic acid reacts with SOCl to prepare the corresponding acid chloride (4), under the catalysis of triethylamine, reacts with the corresponding hydroxyalkyl or aminoalkylfurazan (5) prepared from thiophenol as raw material, Obtain object (I); Synthetic route is as follows: 其中，X、R的定义如权利要求1所述。Wherein, the definitions of X and R are as described in claim 1. 8.权利要求2所述的通式Ⅱ化合物的制备方法，其特征在于：8. the preparation method of the compound of general formula II described in claim 2 is characterized in that: 以间二苯酚(1)为原料，经Vilsmeier-Haack反应得7-羟基苯甲醛(2)，经Knoevenagel反应得到7-羟基香豆素-3-羧酸乙酯(3)，化合物(3)与二溴烷烃反应，得到中间体(4)。化合物(4)再与相应的胺类化合物(HR1)反应得到化合物(6)，化合物(6)经水解、酸化得到化合物(7)，在EDCI作用下，与由苯硫酚为原料制得的相应的羟烷基或氨烷基呋咱(5)反应，转化为目标物(Ⅱ)；合成路线如下：With resorcinol (1) as raw material, 7-hydroxybenzaldehyde (2) is obtained through Vilsmeier-Haack reaction, and 7-hydroxycoumarin-3-carboxylic acid ethyl ester (3) is obtained through Knoevenagel reaction, compound (3) Reaction with dibromoalkane affords intermediate (4). Compound (4) reacts with the corresponding amine compound (HR 1 ) to obtain compound (6). Compound (6) is hydrolyzed and acidified to obtain compound (7). The corresponding hydroxyalkyl or aminoalkyl furazan (5) reaction is converted into the target compound (II); the synthetic route is as follows: 其中，n，R1、X和R的定义如权利要求2所述。Wherein, n, R 1 , X and R are as defined in claim 2. 9.一种药物组合物，其中含有治疗有效量的权利要求1所述的通式I化合物或权利要求2所述的通式Ⅱ化合物或其药学上可接受的盐。9. A pharmaceutical composition, which contains a therapeutically effective amount of the compound of formula I as claimed in claim 1 or the compound of formula II as claimed in claim 2 or a pharmaceutically acceptable salt thereof. 10.权利要求1所述的通式I化合物或权利要求2所述的通式Ⅱ化合物或其药学上可接受的盐在制备治疗肿瘤的药物中的用途，其中肿瘤疾病是肝癌、乳腺癌、宫颈癌、肺癌、结肠癌。10. Use of the compound of general formula I described in claim 1 or the compound of general formula II described in claim 2 or a pharmaceutically acceptable salt thereof in the preparation of a drug for treating tumors, wherein the tumor disease is liver cancer, breast cancer, Cervical cancer, lung cancer, colon cancer.
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