JPS5923319B2 - organic germanium compounds - Google Patents
organic germanium compoundsInfo
- Publication number
- JPS5923319B2 JPS5923319B2 JP55135434A JP13543480A JPS5923319B2 JP S5923319 B2 JPS5923319 B2 JP S5923319B2 JP 55135434 A JP55135434 A JP 55135434A JP 13543480 A JP13543480 A JP 13543480A JP S5923319 B2 JPS5923319 B2 JP S5923319B2
- Authority
- JP
- Japan
- Prior art keywords
- organic germanium
- present
- compounds
- germanium compounds
- compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 150000002291 germanium compounds Chemical class 0.000 title description 9
- 239000000126 substance Substances 0.000 claims description 9
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 230000000844 anti-bacterial effect Effects 0.000 description 6
- -1 organogermanium compound Chemical class 0.000 description 5
- 150000003141 primary amines Chemical class 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 2
- VWHUZNBSDQCMRD-UHFFFAOYSA-N 3-trichlorogermylpropanoyl chloride Chemical compound ClC(=O)CC[Ge](Cl)(Cl)Cl VWHUZNBSDQCMRD-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- XRYJTKGEJGVBCC-UHFFFAOYSA-N 2-germylpropanoic acid Chemical compound CC([GeH3])C(O)=O XRYJTKGEJGVBCC-UHFFFAOYSA-N 0.000 description 1
- JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 description 1
- XJCVRTZCHMZPBD-UHFFFAOYSA-N 3-nitroaniline Chemical compound NC1=CC=CC([N+]([O-])=O)=C1 XJCVRTZCHMZPBD-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 244000063299 Bacillus subtilis Species 0.000 description 1
- 235000014469 Bacillus subtilis Nutrition 0.000 description 1
- 241000272201 Columbiformes Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- RTEXIPZMMDUXMR-UHFFFAOYSA-N benzene;ethyl acetate Chemical compound CCOC(C)=O.C1=CC=CC=C1 RTEXIPZMMDUXMR-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 229910052732 germanium Inorganic materials 0.000 description 1
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical group [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 125000000082 organogermanium group Chemical group 0.000 description 1
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Description
【発明の詳細な説明】
本発明は新規な有機ゲルマニウム化合物に関するもので
ある。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to novel organogermanium compounds.
従来種々の有機ゲルマニウム化合物が合成され、ゲルミ
ルプロピオン酸三二酸化物を用いた低毒性抗腫瘍剤に代
表されるように様々な用途で実用に供され、高い効果を
得ている。Conventionally, various organic germanium compounds have been synthesized and put to practical use in a variety of applications, such as low toxicity antitumor agents using germylpropionate sesquioxide, and have achieved high efficacy.
本発明の発明者も永く有機ゲルマニウム化合物の合成研
究に携わり、鋭意研究を重ねた結果、構造式
）ＧｅＣＨ２ＣＨ２Ｃ０Ｎ＜
で表わされる構造を主骨格に持つ新規な有機ゲルマニウ
ム化合物を見出した。The inventor of the present invention has been involved in research on the synthesis of organic germanium compounds for a long time, and as a result of intensive research, he discovered a novel organic germanium compound having a structure represented by the structural formula) GeCH2CH2C0N< as its main skeleton.
本発明は上記の新規な有機ゲルマニウム化合物に関する
もので、その構成は、一般構造式Ｘ３ＧｅＣＨ２ＣＨ２
ＣＯＮＨＲ
Ｚ（但し、Ｘはハロゲン原子、ＲはＯ、
Ｏ、ｏＺ〔ＺはＨ、一ＣＨ３又は
−ＯＣＨ３のうちの一を表わす〕、゜ＮＯ２□のうちの
一である）で表わされることを特徴とするものである。The present invention relates to the above-mentioned novel organogermanium compound, which has the general structural formula X3GeCH2CH2
CONHR Z (where, This is a characteristic feature.
而して、本発明の有機ゲルマニウム化合物は種種の方法
で合成することができるが、その一例を示せば次の通り
である。Ｘ３ＧｅＣＨ２ＣＨ２ＣＯＸ＋ ２ＮＨ２−Ｒ
Ｘ３ＧｅＣＨ２ＣＨ２ＣＯＮＨＲ＋ＲＮＨ３（Ｘ、Ｒは
前述の通り）即ち、溶媒中もしくは無溶媒で、種々の公
知の方法により合成したβ−トリハロゲノゲルミルプロ
ピオン酸クロライド、例えばβ一トリクロルゲルミルプ
ロピオン酸クロライドに対して、ＮＨ２一Ｒで示される
一級アミン、例えばシクロヘキシルアミン、アニリン、
０−トルイジン、Ｐ−トルイジン、０−アニシジン、Ｐ
−アニシジン、ｍ−ニトロアニリン、α−ナフチルアミ
ン、β−ナフチルアミンのうちの一を、約２倍量室温又
は冷却下に反応させて、数分乃至数時間後に遊離する塩
化水素と前記一級アミンにより生ずる該アミンの塩酸塩
奇除去し、更に溶媒を用いた場合はこれを減圧にて留去
すれば、一般式Ｘ３ＧｅＣＨ２ＣＨ２ＣＯＮＦＩＲで示
される目的物が得られるのである。The organic germanium compound of the present invention can be synthesized by various methods, one example of which is as follows. X3GeCH2CH2COX+ 2NH2-R
X3GeCH2CH2CONHR+RNH3 (X, R are as described above), i.e., β-trihalogenogermylpropionic acid chloride synthesized by various known methods in a solvent or without a solvent, such as β-trichlorogermylpropionic acid chloride, Primary amines represented by NH2R, such as cyclohexylamine, aniline,
0-toluidine, P-toluidine, 0-anisidine, P
- React approximately twice the amount of one of anisidine, m-nitroaniline, α-naphthylamine, and β-naphthylamine at room temperature or under cooling, and after several minutes to several hours, hydrogen chloride is liberated and the primary amine is generated. By removing the hydrochloride of the amine and further distilling off the solvent under reduced pressure, the desired product represented by the general formula X3GeCH2CH2CONFIR can be obtained.
而して、前記一級アミンに例えばシクロヘキシルアミン
を選んだ場合は、７８％の収率でβ一トリクロルゲルミ
ルプロピオン酸シクロヘキシルアミド（以下、物質Ａと
いう）が融点１１６〜１１８ミの結晶として得られ、こ
の化合物の元素分析値はＣ：３２．２０，Ｈ：４．９２
，Ｎ：４．０６（計算値Ｃ：３２．４３，Ｈ：４．８０
，Ｎ：４．２０）であり、核磁気共鳴スペクトルでは、
δ＝１．３，１．８にシクロヘキサン環の特徴あるプロ
トンが観測され、又、赤外線吸収スペクトルでは、図面
に示すように、１７３０ｃｍ−１にカルボニル基、３４
８０ＣＴｒ１−１，３２３０ｃｍ−１及び３１００ｃ！
ｎ−１にＮ−Ｈ結合に基く吸収が表われ、本発明の化合
物の一例の構造を確認することができる。又、一級アミ
ンにその余のものを用いた場合もＣｌ３ＧｅＣＨ２ＣＨ
２ＣＯＮＨＲで示される本発明の化合物が得られ、それ
らの構造も同様に確認された。上記方法で合成された本
発明の化合物はすべて脂溶性で、アルコール、アセトン
、ベンゼン、酢酸エステル等の溶媒に可溶であり、又、
ゲルマニウム原子に結合している三個のハロゲン原子は
極めて反応性に富み容易にアルキル化することができる
という性質を持つている。When, for example, cyclohexylamine is selected as the primary amine, β-trichlorogermylpropionic acid cyclohexylamide (hereinafter referred to as substance A) can be obtained as crystals with a melting point of 116 to 118 mm with a yield of 78%. , the elemental analysis values of this compound are C: 32.20, H: 4.92
, N: 4.06 (calculated value C: 32.43, H: 4.80
, N: 4.20), and in the nuclear magnetic resonance spectrum,
Characteristic protons of the cyclohexane ring were observed at δ = 1.3 and 1.8, and in the infrared absorption spectrum, as shown in the drawing, there was a carbonyl group at 1730 cm-1, 34
80CTr1-1, 3230cm-1 and 3100c!
Absorption based on the N-H bond appears at n-1, and the structure of an example of the compound of the present invention can be confirmed. Also, when other primary amines are used, Cl3GeCH2CH
Compounds of the invention designated 2CONHR were obtained and their structures were likewise confirmed. The compounds of the present invention synthesized by the above method are all fat-soluble and soluble in solvents such as alcohol, acetone, benzene, and acetate, and
The three halogen atoms bonded to the germanium atom are extremely reactive and can be easily alkylated.
更に本発明の物質はすべて高い抗菌性を有しており、例
えば、前記物質Ａはこれを平板法により検定したところ
、ＢａｃｉｌｌｕｓｓｕｂｔｉｌｉｓＰＣＩ２ｌ９や、
ＰｓｅｕｄＯｍＯｕａｓａｅｒｕｇｉｎＯｓａＰ−３を
始めとして数種の検定菌に対し強い抗菌力を示し、その
他の化合物も広くて強力な抗菌スペクトルを有している
ことが明らかとなつた。Furthermore, all the substances of the present invention have high antibacterial properties; for example, when the substance A was assayed by the plate method, it was found that Bacillus subtilis PCI2l9,
It has become clear that it exhibits strong antibacterial activity against several types of test bacteria, including PseudOmOuasaeruginOsaP-3, and that other compounds also have a broad and strong antibacterial spectrum.
次に本発明の実施の一例を示せば次の通りである。Next, an example of implementing the present invention will be described as follows.
β一トリクロルゲルミルプロピオン酸シクロヘキシルア
ミド（物質Ａ）の製造例気密容器内においてｎ−ヘキサ
ン等の溶媒に溶解したβ一トリクロルゲルミルプロピオ
ン酸クロライド２．７ｇ（０．０１モノ（ハ）を氷冷下
の温度に保ちｎ−ヘキサンに溶解したシクロヘキシルア
ミン２．２ｇ（０．０２２モル）を撹拌しながら滴加し
、さらに３０分撹拌を続け反応を完結させる。Production example of β-trichlorogermylpropionic acid cyclohexylamide (substance A) In an airtight container, 2.7 g of β-trichlorogermylpropionic acid chloride (0.01 mono(c)) dissolved in a solvent such as n-hexane was poured into ice. While keeping the temperature cool, 2.2 g (0.022 mol) of cyclohexylamine dissolved in n-hexane is added dropwise with stirring, and stirring is continued for an additional 30 minutes to complete the reaction.
反応液に水を加えて未反応のシクロヘキシルアミン及び
シクロヘキシルアミンの塩酸化を水層に移行させた後反
応生成物をベンゼ７→酢酸エチルエステルで抽出する。
ベンゼン一酢酸エチルエステルを留去し残渣に少量のア
セトンを加えたところ、本発明の化合物β一トリクロル
ゲルミルプロピオン酸シクロヘキシルアミド（Ｃｌ３Ｇ
ｅＣ鳩Ｃ↓ＣＯＮＨ−（４１］１１）の結晶２．６ｇ（
収率７８％）が得られた。この物質Ａの融点は１１６〜
１１８らでその構造は機器分析の結果により前述の通り
確められた。更に一級アミンにシクロヘキシルアミン以
外のものを用いた場合も、前記実施例と全く同様の製造
方法により表１に示すように本発明の化合物である物質
Ｂ−１が得られ、表２に示すような機器分析の結果から
その構造が確認された。而して、本発明の有機ゲルマニ
ウム化合物は前述のように通り抗菌性を有するが、その
実験例を示せば次の通りである。Water is added to the reaction solution to transfer unreacted cyclohexylamine and hydrochloride of cyclohexylamine to the aqueous layer, and then the reaction product is extracted with benzene 7→ethyl acetate.
When benzene monoacetic acid ethyl ester was distilled off and a small amount of acetone was added to the residue, the compound of the present invention, β-trichlorogermylpropionic acid cyclohexylamide (Cl3G
2.6 g of crystals of eC pigeon C↓CONH-(41]11) (
A yield of 78%) was obtained. The melting point of this substance A is 116~
118 et al., whose structure was confirmed by the results of instrumental analysis as described above. Furthermore, even when a primary amine other than cyclohexylamine is used, substance B-1, which is a compound of the present invention, is obtained as shown in Table 1 by the same manufacturing method as in the above example, and as shown in Table 2. The structure was confirmed from the results of extensive instrumental analysis. The organic germanium compound of the present invention has antibacterial properties as described above, and experimental examples thereof are as follows.
本発明有機ゲルマニウム化合物Ａ−１の抗菌スベクトル
の検定化合物Ａ−Ｚを各々滅菌水１Ｔｔｅ．に懸濁し、
濾紙製デイスクに染み込ませて十分乾燥した後、検定プ
レート（検定菌重層）上に置き、２４時間後に阻止円の
直径を測定したところ下記表３に示すような結果が得ら
れた。Antibacterial vector testing of the organic germanium compound A-1 of the present invention Compounds A-Z were each added to 1 Tte. of sterilized water. suspended in
After it was soaked into a filter paper disc and sufficiently dried, it was placed on a test plate (overlayered with test bacteria), and the diameter of the inhibition circle was measured 24 hours later, and the results shown in Table 3 below were obtained.
本発明の有機ゲルマニウム化合物は上述の通りであつて
、簡単な方法で収率良く合成され、且つ、高い抗菌性を
有しているので、その利用性は極めて大なるものがある
。The organic germanium compound of the present invention, as described above, can be synthesized in a simple manner with good yield and has high antibacterial properties, so its utility is extremely great.
図面は本発明有機ゲルマニウム化合物のうち、トリクロ
ルゲルミルプロピオン酸シクロヘキシルアミドＣｌ３Ｇ
ｅＣＨ２ＣＨ２ＣＯＮＨ−Ｃ６Ｈｌｌの赤外線吸収スペ
クトルを示したものである。The drawing shows trichlorogermylpropionic acid cyclohexylamide Cl3G among the organic germanium compounds of the present invention.
It shows the infrared absorption spectrum of eCH2CH2CONH-C6Hll.
Claims (1)
があります▼、▲数式、化学式、表等があります▼、▲
数式、化学式、表等があります▼〔ＺはＨ、−ＣＨ＿３
又は−ＯＣＨ＿３のうちの一を表わす〕、▲数式、化学
式、表等があります▼▲数式、化学式、表等があります
▼のうちの一である）で表わされることを特徴とする有
機ゲルマニウム化合物。[Scope of Claims] 1 General structural formula
There are mathematical formulas, chemical formulas, tables, etc. ▼ [Z is H, -CH_3
or -OCH_3], ▲ has a mathematical formula, chemical formula, table, etc. ▼ ▲ has a mathematical formula, chemical formula, table, etc. ▼ is one of the following).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP55135434A JPS5923319B2 (en) | 1980-09-29 | 1980-09-29 | organic germanium compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP55135434A JPS5923319B2 (en) | 1980-09-29 | 1980-09-29 | organic germanium compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5759899A JPS5759899A (en) | 1982-04-10 |
| JPS5923319B2 true JPS5923319B2 (en) | 1984-06-01 |
Family
ID=15151624
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP55135434A Expired JPS5923319B2 (en) | 1980-09-29 | 1980-09-29 | organic germanium compounds |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5923319B2 (en) |
-
1980
- 1980-09-29 JP JP55135434A patent/JPS5923319B2/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5759899A (en) | 1982-04-10 |
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