MD4520C1 - N-(4-бутоксифенил)-2-(пиридин-2-илметилиден)гидразинкарботиоамид в качестве ингибитора роста клеток T-47D рака молочной железы - Google Patents
N-(4-бутоксифенил)-2-(пиридин-2-илметилиден)гидразинкарботиоамид в качестве ингибитора роста клеток T-47D рака молочной железы Download PDFInfo
- Publication number
- MD4520C1 MD4520C1 MDA20160141A MD20160141A MD4520C1 MD 4520 C1 MD4520 C1 MD 4520C1 MD A20160141 A MDA20160141 A MD A20160141A MD 20160141 A MD20160141 A MD 20160141A MD 4520 C1 MD4520 C1 MD 4520C1
- Authority
- MD
- Moldova
- Prior art keywords
- breast cancer
- butoxyphenyl
- pyridin
- ylmethylidene
- cancer cells
- Prior art date
Links
- 206010006187 Breast cancer Diseases 0.000 title claims abstract description 18
- 208000026310 Breast neoplasm Diseases 0.000 title claims abstract description 18
- UUOPJNVEEGYJRI-UHFFFAOYSA-N 1-(4-butoxyphenyl)-3-(pyridin-2-ylmethylideneamino)thiourea Chemical compound C(CCC)OC1=CC=C(C=C1)NC(=S)NN=CC1=NC=CC=C1 UUOPJNVEEGYJRI-UHFFFAOYSA-N 0.000 title claims abstract description 7
- 239000003966 growth inhibitor Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 16
- 239000003112 inhibitor Substances 0.000 claims abstract description 10
- 230000009702 cancer cell proliferation Effects 0.000 claims description 3
- 239000003814 drug Substances 0.000 abstract description 6
- 230000012010 growth Effects 0.000 abstract description 6
- 238000011282 treatment Methods 0.000 abstract description 3
- 150000002894 organic compounds Chemical class 0.000 abstract description 2
- 150000003583 thiosemicarbazides Chemical class 0.000 abstract description 2
- 229940127089 cytotoxic agent Drugs 0.000 abstract 1
- 239000002254 cytotoxic agent Substances 0.000 abstract 1
- 230000002265 prevention Effects 0.000 abstract 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- -1 N-(4-butoxyphenyl)-2-(pyridin-2-ylmethylidene)-hydrazine Chemical compound 0.000 description 8
- 239000000203 mixture Substances 0.000 description 6
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
- AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 description 4
- 230000001093 anti-cancer Effects 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 125000001309 chloro group Chemical group Cl* 0.000 description 4
- 229910052802 copper Inorganic materials 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 230000035755 proliferation Effects 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- BRWIZMBXBAOCCF-UHFFFAOYSA-N thiosemicarbazide group Chemical group NNC(=S)N BRWIZMBXBAOCCF-UHFFFAOYSA-N 0.000 description 4
- CSDSSGBPEUDDEE-UHFFFAOYSA-N 2-formylpyridine Chemical compound O=CC1=CC=CC=N1 CSDSSGBPEUDDEE-UHFFFAOYSA-N 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 230000003327 cancerostatic effect Effects 0.000 description 2
- 238000001516 cell proliferation assay Methods 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000001085 cytostatic effect Effects 0.000 description 2
- 229960004679 doxorubicin Drugs 0.000 description 2
- 239000012091 fetal bovine serum Substances 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 2
- 150000002540 isothiocyanates Chemical class 0.000 description 2
- 238000011321 prophylaxis Methods 0.000 description 2
- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 1
- QVAMIJSFEORYOS-UHFFFAOYSA-N 1-butoxy-4-isothiocyanatobenzene Chemical compound CCCCOC1=CC=C(N=C=S)C=C1 QVAMIJSFEORYOS-UHFFFAOYSA-N 0.000 description 1
- VOXZDWNPVJITMN-ZBRFXRBCSA-N 17β-estradiol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 VOXZDWNPVJITMN-ZBRFXRBCSA-N 0.000 description 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- UBRIHZOFEJHMIT-UHFFFAOYSA-N 4-butoxyaniline Chemical compound CCCCOC1=CC=C(N)C=C1 UBRIHZOFEJHMIT-UHFFFAOYSA-N 0.000 description 1
- 229920002307 Dextran Polymers 0.000 description 1
- 101000666730 Homo sapiens T-complex protein 1 subunit alpha Proteins 0.000 description 1
- 102000004877 Insulin Human genes 0.000 description 1
- 108090001061 Insulin Proteins 0.000 description 1
- ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 description 1
- 229930182816 L-glutamine Natural products 0.000 description 1
- 229930182555 Penicillin Natural products 0.000 description 1
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
- 239000012979 RPMI medium Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 102100038410 T-complex protein 1 subunit alpha Human genes 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000004113 cell culture Methods 0.000 description 1
- 230000010261 cell growth Effects 0.000 description 1
- 239000006285 cell suspension Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000000973 chemotherapeutic effect Effects 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000000824 cytostatic agent Substances 0.000 description 1
- 230000009615 deamination Effects 0.000 description 1
- 238000006481 deamination reaction Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229960005309 estradiol Drugs 0.000 description 1
- 229930182833 estradiol Natural products 0.000 description 1
- 229940011871 estrogen Drugs 0.000 description 1
- 239000000262 estrogen Substances 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 229940125396 insulin Drugs 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- KNDXZFMNQKSIHU-UHFFFAOYSA-N methyl 2,3,5,6-tetrachloro-4-methylsulfanylcarbonylbenzoate Chemical compound COC(=O)C1=C(Cl)C(Cl)=C(C(=O)SC)C(Cl)=C1Cl KNDXZFMNQKSIHU-UHFFFAOYSA-N 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 238000010183 spectrum analysis Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- SRVJKTDHMYAMHA-WUXMJOGZSA-N thioacetazone Chemical compound CC(=O)NC1=CC=C(\C=N\NC(N)=S)C=C1 SRVJKTDHMYAMHA-WUXMJOGZSA-N 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Изобретение относится к химии и медицине, а именно к биологически активному органическому соединению класса тиосемикарбазидов и может найти применение в медицине в качестве цитостатического препарата при профилактике и лечении рака молочной железы.Сущность изобретения заключается в применении нового соединения N-(4-бутоксифенил)-2-(пиридин-2-илметилиден)гидразинкарботиоамид формулы:в качестве ингибитора роста и размножения клеток T-47D рака молочной железы, который при концентрации 10-7 моль/л ингибирует рост и размножение 44,2% клеток T-47D рака молочной железы.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| MDA20160141A MD4520C1 (ru) | 2016-12-16 | 2016-12-16 | N-(4-бутоксифенил)-2-(пиридин-2-илметилиден)гидразинкарботиоамид в качестве ингибитора роста клеток T-47D рака молочной железы |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| MDA20160141A MD4520C1 (ru) | 2016-12-16 | 2016-12-16 | N-(4-бутоксифенил)-2-(пиридин-2-илметилиден)гидразинкарботиоамид в качестве ингибитора роста клеток T-47D рака молочной железы |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| MD4520B1 MD4520B1 (ru) | 2017-10-31 |
| MD4520C1 true MD4520C1 (ru) | 2018-05-31 |
Family
ID=60243236
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MDA20160141A MD4520C1 (ru) | 2016-12-16 | 2016-12-16 | N-(4-бутоксифенил)-2-(пиридин-2-илметилиден)гидразинкарботиоамид в качестве ингибитора роста клеток T-47D рака молочной железы |
Country Status (1)
| Country | Link |
|---|---|
| MD (1) | MD4520C1 (ru) |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5281715A (en) * | 1992-05-13 | 1994-01-25 | Yale University | 2-formylpyridine thiosemicarbazone compounds |
| EP2240175B1 (en) * | 2008-02-11 | 2013-01-02 | The Government of the United States of America as represented by the Secretary of the Department of Health and Human Services | Compounds with mdr1-inverse activity |
| MD3995C2 (ru) * | 2009-05-11 | 2010-07-31 | Государственный Университет Молд0 | Использование ди(µ-Oфенокси)-ди{[2-(4-аминобензолсульфамидо)-5-этил-1,3,4-тиадиазол]-3,5-дибромсалицилидентиосемикарбазоната(-1) меди} в качестве ингибитора роста и размножения клеток Т-47D рака молочной железы |
| WO2012033601A1 (en) * | 2010-08-20 | 2012-03-15 | The United States Of America, As Represented By The Secretary, Department Of Health & Human Services | Thiosemicarbazones with mdr1 - inverse activity |
| MD4132C1 (ru) * | 2010-12-13 | 2012-05-31 | Государственный Университет Молд0 | Ди(µ-S)-бис{хлоро-[фенил(пиридин-2-ил)метанон-тиосемикарбазонато(1-)]медь} проявляющий свойство ингибитора пролиферации клеток T-47D рака молочной железы |
| MD4215C1 (ru) * | 2012-07-09 | 2013-11-30 | Государственный Университет Молд0 | Ингибитор миелоидой лейкемии человека на основе N-(4-(5-( пиридин-2-ил)-4,5-дигидро-1Н-пиразол-3-ил)фенил)-2-(пиридин-2-илметилен)-гидразинкарботиоамида |
| MD4349C1 (ru) * | 2014-06-23 | 2015-12-31 | Государственный Университет Молд0 | Соединение N-(3-метоксифенил)-2-(пиридин-2-илметилен)-гидразинкарботиоамид - ингибитор пролиферации клеток MeW-164 меланомы человека |
| MD4407C1 (ru) * | 2015-04-29 | 2016-10-31 | Государственный Университет Молд0 | Ингибитор клеток HL-60 миелоидной лейкемии человека на основе гидрата хлорида бис[N-(проп-2-ен-1-ил)-2-(пиридин-2-илметилиден)-гидразинкарботиоамид]-никеля(II) |
-
2016
- 2016-12-16 MD MDA20160141A patent/MD4520C1/ru not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| MD4520B1 (ru) | 2017-10-31 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Hanif et al. | Design, spectral characterization and biological studies of transition metal (II) complexes with triazole Schiff bases | |
| Yernale et al. | Indole core-based Copper (II), Cobalt (II), Nickel (II) and Zinc (II) complexes: Synthesis, spectral and biological study | |
| Han et al. | Scutellarin derivatives as apoptosis inducers: Design, synthesis and biological evaluation | |
| Chohan et al. | Antibacterial and antifungal metal based triazole Schiff bases | |
| Tahir et al. | DNA-binding studies and biological activities of new nitrosubstituted acyl thioureas | |
| Mehta et al. | Synthesis of 1, 3, 5-trisubstituted pyrazoline derivatives and their applications | |
| Zhang et al. | Novel camphor-based pyrimidine derivatives induced cancer cell death through a ROS-mediated mitochondrial apoptosis pathway | |
| Rahman et al. | Morpholine or methylpiperazine and salicylaldimine based heteroleptic square planner platinum (II) complexes: In vitro anticancer study and growth retardation effect on E. coli | |
| Al-Asadi | Synthesis, DFT calculation and biological activity of some organotellurium compounds containing azomethine group | |
| Guimaraes et al. | Naphthoquinone-based hydrazone hybrids: synthesis and potent activity against cancer cell lines | |
| Galassi et al. | Synthesis and characterization of azolate gold (I) phosphane complexes as thioredoxin reductase inhibiting antitumor agents | |
| Karataş et al. | Water-soluble silver (I) complexes with N-donor benzimidazole ligands containing an imidazolium core: Stability and preliminary biological studies | |
| Turomsha et al. | Copper (ii) complexes of sterically hindered phenolic Schiff bases: synthesis, characterization, interaction with biomolecules, and antioxidant and antimicrobial activity | |
| Chohan et al. | Metal‐based isatin‐bearing sulfonamides: their synthesis, characterization and biological properties | |
| MD4132C1 (ru) | Ди(µ-S)-бис{хлоро-[фенил(пиридин-2-ил)метанон-тиосемикарбазонато(1-)]медь} проявляющий свойство ингибитора пролиферации клеток T-47D рака молочной железы | |
| MD4215C1 (ru) | Ингибитор миелоидой лейкемии человека на основе N-(4-(5-( пиридин-2-ил)-4,5-дигидро-1Н-пиразол-3-ил)фенил)-2-(пиридин-2-илметилен)-гидразинкарботиоамида | |
| Chakraborty et al. | Tunable and improved antiproliferative activity of Pt (II)‐based organometallics bearing alkynyls and 1, 2, 3‐triazole moieties | |
| Sahu et al. | Synthesis, characterization and biological activity of 2-methyl-3-aminoquinazolin-4 (3H)-ones Schiff bases | |
| MD4520C1 (ru) | N-(4-бутоксифенил)-2-(пиридин-2-илметилиден)гидразинкарботиоамид в качестве ингибитора роста клеток T-47D рака молочной железы | |
| CN105198937A (zh) | 一种含有3,5-二氯水杨醛缩4-硝基邻氨基酚Schiff碱与吡啶的钴配合物及其制备方法和应用 | |
| Ndifon et al. | Synthesis, Structure, Hirshfeld surface analysis and Anti-oxidant studies on 2-(4-dimethylamino) benzylidene) hydrazine-1-carbothioamide | |
| CN108017608A (zh) | 一类黄酮衍生物及其制备方法和用途 | |
| CN107337633B (zh) | 含吡啶盐的戊二烯酮类化合物及其制备方法及应用 | |
| Küçükbay et al. | Synthesis and antimicrobial activities of some transition metal benzimidazole complexes | |
| Al-Khazraji | Synthesis, Characterization, and Evaluation of MCF-7 (Breast Cancer) for Schiff, Mannich Bases, and Their Complexes |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FG4A | Patent for invention issued | ||
| KA4A | Patent for invention lapsed due to non-payment of fees (with right of restoration) | ||
| MM4A | Patent for invention definitely lapsed due to non-payment of fees |