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

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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
Application number
MDA20100129A
Other languages
Romanian (ro)
Russian (ru)
Other versions
MD4126B1 (en
Inventor
Аурелиан ГУЛЯ
Анжела ЖАЛБЭ
Никанор БАРБА
Виктор ЦАПКОВ
Лариса СОФРОНИ
Дональд ПОЙРИЕР
Original Assignee
Государственный Университет Молд0
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Государственный Университет Молд0 filed Critical Государственный Университет Молд0
Priority to MDA20100129A priority Critical patent/MD4126C1/en
Publication of MD4126B1 publication Critical patent/MD4126B1/en
Publication of MD4126C1 publication Critical patent/MD4126C1/en

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  • 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.
MDA20100129A 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 MD4126C1 (en)

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

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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

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MD (1) MD4126C1 (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
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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)

Patent Citations (13)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
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 *

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