MD4126C1 - N,N'-[4,4'-(perfluoro-1,4-phenylenedioxy)-bis(4,1-phenylene)]-bis[2-(pyridine-2-ilmethylene)hydrazinecarbothioamide] and use thereof as prostate cancer LNCaP cell proliferation inhibitor - Google Patents
N,N'-[4,4'-(perfluoro-1,4-phenylenedioxy)-bis(4,1-phenylene)]-bis[2-(pyridine-2-ilmethylene)hydrazinecarbothioamide] and use thereof as prostate cancer LNCaP cell proliferation inhibitor Download PDFInfo
- Publication number
- MD4126C1 MD4126C1 MDA20100129A MD20100129A MD4126C1 MD 4126 C1 MD4126 C1 MD 4126C1 MD A20100129 A MDA20100129 A MD A20100129A MD 20100129 A MD20100129 A MD 20100129A MD 4126 C1 MD4126 C1 MD 4126C1
- Authority
- MD
- Moldova
- Prior art keywords
- bis
- phenylenedioxy
- perfluoro
- prostate cancer
- ilmethylene
- Prior art date
Links
- 206010060862 Prostate cancer Diseases 0.000 title abstract 3
- 208000000236 Prostatic Neoplasms Diseases 0.000 title abstract 3
- -1 4,1-phenylene Chemical group 0.000 title abstract 2
- 230000004663 cell proliferation Effects 0.000 title abstract 2
- BRWIZMBXBAOCCF-UHFFFAOYSA-N hydrazinecarbothioamide Chemical compound NNC(N)=S BRWIZMBXBAOCCF-UHFFFAOYSA-N 0.000 title abstract 2
- 239000003112 inhibitor Substances 0.000 title abstract 2
- 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 abstract 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- CSDSSGBPEUDDEE-UHFFFAOYSA-N 2-formylpyridine Chemical compound O=CC1=CC=CC=N1 CSDSSGBPEUDDEE-UHFFFAOYSA-N 0.000 abstract 1
- OLYSJNQUDPLGNG-UHFFFAOYSA-N 4-[4-(4-aminophenoxy)-2,3,5,6-tetrafluorophenoxy]aniline Chemical compound C1=CC(N)=CC=C1OC(C(=C1F)F)=C(F)C(F)=C1OC1=CC=C(N)C=C1 OLYSJNQUDPLGNG-UHFFFAOYSA-N 0.000 abstract 1
- 230000001093 anti-cancer Effects 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 230000009615 deamination Effects 0.000 abstract 1
- 238000006481 deamination reaction Methods 0.000 abstract 1
- 229940042396 direct acting antivirals thiosemicarbazones Drugs 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 238000006698 hydrazinolysis reaction Methods 0.000 abstract 1
- 230000003993 interaction Effects 0.000 abstract 1
- 230000002265 prevention Effects 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
- 150000003584 thiosemicarbazones Chemical class 0.000 abstract 1
- 230000009466 transformation Effects 0.000 abstract 1
- 238000000844 transformation Methods 0.000 abstract 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
Abstract
The invention relates to organic chemistry, namely to the synthesis of biologically active compounds from the class of thiosemicarbazones and can be used in medicine for the prevention and treatment of prostate cancer.Summary of the invention consists in that it was synthesized a new compound proceeding from 4,4'-(perfluoro-1,4-phenylenedioxy)dianiline, which was subjected to the following series of transformations: conversion into bis-thiourea upon interaction with dimethylthiouram; deamination with sulfuric acid in bis-isothiocyanate; conversion upon hydrazinolysis into appropriate bis-thiosemicarbazide, which was further condensed with 2-formylpyridine. Finally, it is obtained N,N'-[4,4'-(perfluoro-1,4-phenylenedioxy)-bis(4,1-phenylene)]-bis[2-(pyridine-2-ilmethylene) hydrazinecarbothioamide] with the formula:The resulting bis-thiosemicarbazone possesses anticancer activity, which 1.5 times exceeds the activity of doxorubicine.The technical result of the invention is to expand the range of prostate cancer LNCaP cell proliferation inhibitors.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| MDA20100129A MD4126C1 (en) | 2010-11-15 | 2010-11-15 | N,N'-[4,4'-(perfluoro-1,4-phenylenedioxy)-bis(4,1-phenylene)]-bis[2-(pyridine-2-ilmethylene)hydrazinecarbothioamide] and use thereof as prostate cancer LNCaP cell proliferation inhibitor |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| MDA20100129A MD4126C1 (en) | 2010-11-15 | 2010-11-15 | N,N'-[4,4'-(perfluoro-1,4-phenylenedioxy)-bis(4,1-phenylene)]-bis[2-(pyridine-2-ilmethylene)hydrazinecarbothioamide] and use thereof as prostate cancer LNCaP cell proliferation inhibitor |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| MD4126B1 MD4126B1 (en) | 2011-09-30 |
| MD4126C1 true MD4126C1 (en) | 2012-04-30 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MDA20100129A MD4126C1 (en) | 2010-11-15 | 2010-11-15 | N,N'-[4,4'-(perfluoro-1,4-phenylenedioxy)-bis(4,1-phenylene)]-bis[2-(pyridine-2-ilmethylene)hydrazinecarbothioamide] and use thereof as prostate cancer LNCaP cell proliferation inhibitor |
Country Status (1)
| Country | Link |
|---|---|
| MD (1) | MD4126C1 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MD4215C1 (en) * | 2012-07-09 | 2013-11-30 | Государственный Университет Молд0 | Inhibitor of human myeloid leukemia based on N-(4-(5-(pyridin-2-yl)-4,5-dihydro-1H-pyrazol-3-yl)phenyl)-2-(pyridin-2-ylmethylen)-hydrazinecarbothioamide |
Citations (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5242883A (en) * | 1975-10-03 | 1977-04-04 | Otou Kenkyusho | Method of preparing thiosemicarbazones having carcinostatic activity |
| US5281715A (en) * | 1992-05-13 | 1994-01-25 | Yale University | 2-formylpyridine thiosemicarbazone compounds |
| US5767134A (en) * | 1997-05-15 | 1998-06-16 | Vion Pharmaceuticals, Inc. | Prodrug forms of ribonucleotide reductase inhibitors 3-AP and 3-AMP |
| US5869676A (en) * | 1997-05-15 | 1999-02-09 | Vion Pharmaceuticals, Inc. | Process for the synthesis of ribonucleotide reductase inhibitors 3-AP and 3-AMP |
| MD943G2 (en) * | 1997-07-10 | 1999-02-28 | Государственный Университет Молд0 | Process for obtaining isothiocyanate benzoic acids |
| MD1274G2 (en) * | 1999-01-20 | 2000-02-29 | Государственный Университет Молд0 | Process for oligo-4-(4-thiocarbazido)-styrene preparation |
| GB2392386A (en) * | 2002-08-29 | 2004-03-03 | Cxr Biosciences Ltd | Medical use of perfluoro compounds |
| US6794400B2 (en) * | 2001-06-01 | 2004-09-21 | Cytovia, Inc. | 4-substituted-1-(arylmethylidene)thiosemicarbazide, 4-substituted-1-(arylcarbonyl)thiosemicarbazide and analogs as activators of caspases and inducers of apoptosis and the use thereof |
| WO2007035489A2 (en) * | 2005-09-16 | 2007-03-29 | Government Of The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Methods of treating or preventing cancer using pyridine carboxaldehyde pyridine thiosemicarbazone radiosensitizing agents |
| MD3771G2 (en) * | 2008-04-30 | 2009-07-31 | Государственный Университет Молд0 | Inhibitors of 17β-HSD enzyme, stimulator for prostate cancer cell multiplication |
| MD3996C2 (en) * | 2009-05-25 | 2010-07-31 | Государственный Университет Молд0 | Perchlorates of 5-R-salicylidene-4-phenylthiosemicarbazonato(1-)-aquacopper(II) possessing properties of inhibitors of 17b-HSD enzyme activity (type 1) |
-
2010
- 2010-11-15 MD MDA20100129A patent/MD4126C1/en not_active IP Right Cessation
Patent Citations (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5242883A (en) * | 1975-10-03 | 1977-04-04 | Otou Kenkyusho | Method of preparing thiosemicarbazones having carcinostatic activity |
| US5281715A (en) * | 1992-05-13 | 1994-01-25 | Yale University | 2-formylpyridine thiosemicarbazone compounds |
| RU2198875C2 (en) * | 1997-05-15 | 2003-02-20 | Вион Фармасьютикалз, Инк. | Methods of synthesis of pyridine-2-carboxaldehyde thiosemicarbazones and intermediate pyridine-2-carboxaldehydes |
| US5869676A (en) * | 1997-05-15 | 1999-02-09 | Vion Pharmaceuticals, Inc. | Process for the synthesis of ribonucleotide reductase inhibitors 3-AP and 3-AMP |
| US5767134A (en) * | 1997-05-15 | 1998-06-16 | Vion Pharmaceuticals, Inc. | Prodrug forms of ribonucleotide reductase inhibitors 3-AP and 3-AMP |
| RU2199531C2 (en) * | 1997-05-15 | 2003-02-27 | Вион Фармасьютикалз, Инк. | Pyridine-2-carboxaldehyde thiosemicarbazones and pharmaceutical composition based on thereof |
| MD943G2 (en) * | 1997-07-10 | 1999-02-28 | Государственный Университет Молд0 | Process for obtaining isothiocyanate benzoic acids |
| MD1274G2 (en) * | 1999-01-20 | 2000-02-29 | Государственный Университет Молд0 | Process for oligo-4-(4-thiocarbazido)-styrene preparation |
| US6794400B2 (en) * | 2001-06-01 | 2004-09-21 | Cytovia, Inc. | 4-substituted-1-(arylmethylidene)thiosemicarbazide, 4-substituted-1-(arylcarbonyl)thiosemicarbazide and analogs as activators of caspases and inducers of apoptosis and the use thereof |
| GB2392386A (en) * | 2002-08-29 | 2004-03-03 | Cxr Biosciences Ltd | Medical use of perfluoro compounds |
| WO2007035489A2 (en) * | 2005-09-16 | 2007-03-29 | Government Of The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Methods of treating or preventing cancer using pyridine carboxaldehyde pyridine thiosemicarbazone radiosensitizing agents |
| MD3771G2 (en) * | 2008-04-30 | 2009-07-31 | Государственный Университет Молд0 | Inhibitors of 17β-HSD enzyme, stimulator for prostate cancer cell multiplication |
| MD3996C2 (en) * | 2009-05-25 | 2010-07-31 | Государственный Университет Молд0 | Perchlorates of 5-R-salicylidene-4-phenylthiosemicarbazonato(1-)-aquacopper(II) possessing properties of inhibitors of 17b-HSD enzyme activity (type 1) |
Non-Patent Citations (6)
| Title |
|---|
| 3-Aminopyridine-2-carboxaldehyde thiosemicarbazone (The page was last modified on 29 November 2010), (regăsit în Internet la 2011.07.21, url: http://en.wikipedia.org/wiki/Triapine) * |
| Brockman R.W. et al: "Observations on the Antileukemic Activity of Pyridine-2-Carboxaldehyde Thiosemicarbazones and Thiocarbazone", Cancer Res. 1956 vol.16, p.167 * |
| Giorgio Pelosi. Thiosemicarbazone Metal Complexes: from Structure to Activity. The Open Crystallography Journal, 2010, 3, 16-28 (Referinţele de pe pag. 16-17) * |
| Laplante Y., Poirer D. Proliferative effect of androst-4-ene-3,17-dione and its metabolites in the androgen-sensitive LNCaP cell line. Steroids, 2008, vol. 73, Nr. 3, p. 266-271 * |
| Prostate cancer (The page was last modified on 19 July 2011) (regăsit în Internet la 2011.07.21, url: http://en.wikipedia.org/wiki/Prostate_cancer ) * |
| Машковский М.Д. Лекарственные средства. Новая волна, Москва, 2008, с. 1206 * |
Also Published As
| Publication number | Publication date |
|---|---|
| MD4126B1 (en) | 2011-09-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FG4A | Patent for invention issued | ||
| MM4A | Patent for invention definitely lapsed due to non-payment of fees |