Synthesis and antituberculosis activity of novel 5-styryl-4-(hetero)aryl-pyrimidines via combination of the Pd-catalyzed Suzuki cross-coupling and S-N(H) reactions / Kravchenko Marionella A.,Verbitskiy Egor V.,Medvinskiy Igor D.,Rusinov Gennady L.,Charushin Valery N. // BIOORGANIC \& MEDICINAL CHEMISTRY LETTERS. - 2014. - V. 24, l. 14. - P. 3118-3120.

ISSN/EISSN:

0960-894X / 1464-3405

Type:

Article

Abstract:

Combination of the Suzuki cross-coupling and nucleophilic aromatic substitution of hydrogen (S-N(H)) reactions proved to be a convenient method for the synthesis of 5-styryl-4-(hetero)aryl substituted pyrimidines from commercially available 5-bromopyrimidine. All intermediate 5-bromo-4-(hetero)aryl substituted pyrimidines and also the targeted 5-styryl-4-(hetero)arylpyrimidines were found to be active in micromolar concentrations in vitro against Mycobacterium tuberculosis H(37)Rv, avium, terrae, and multidrug-resistant strain isolated from tuberculosis patients in Ural region (Russia). It has been found that some of these compounds possess a low toxicity and have a bacteriostatic effect, comparable and even higher with that of first-line antituberculosis drugs. (C) 2014 Elsevier Ltd. All rights reserved.

Author keywords:

Pyrimidine; Antimicobacterial; Tuberculosis; Cross-coupling; Nucleophilic aromatic substitution of hydrogen MYCOBACTERIUM-TUBERCULOSIS; ANTIMYCOBACTERIAL ACTIVITY; ANALOGS; PURINES; AGENTS; DRUGS

DOI:

10.1016/j.bmcl.2014.05.006

Web of Science ID:

ISI:000338809400026

Соавторы в МНС:

Другие поля

Поле	Значение
Month	JUL 15
Publisher	PERGAMON-ELSEVIER SCIENCE LTD
Address	THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND
Language	English
EISSN	1464-3405
Keywords-Plus	MYCOBACTERIUM-TUBERCULOSIS; ANTIMYCOBACTERIAL ACTIVITY; ANALOGS; PURINES; AGENTS; DRUGS
Research-Areas	Pharmacology \& Pharmacy; Chemistry
Web-of-Science-Categories	Chemistry, Medicinal; Chemistry, Organic
Author-Email	Verbitslcy@ios.uran.ru
Funding-Acknowledgement	Ural Branch of the Russian Academy of Sciences {[}12-P-3-1014, 12-P-3-1030, 12-T-3-1025, 12-T-3-1031, 13-3-019-UMA]; Russian Foundation for Basic Research {[}13-03-96049-r\_ural\_a, 13-03-90606-Arm\_a, 14-03-31040-mol\_a]; Council on Grants at the President of the Russian Federation (Program of State Support for Leading Scientific Schools of the Russian Federation and Young Scientists) {[}MK-3939.2014.3]
Funding-Text	This work was supported by the Ural Branch of the Russian Academy of Sciences (Grants Nos. 12-P-3-1014, 12-P-3-1030, 12-T-3-1025, 12-T-3-1031 and 13-3-019-UMA), the Russian Foundation for Basic Research (research projects Nos. 13-03-96049-r\_ural\_a, 13-03-90606-Arm\_a and 14-03-31040-mol\_a), the Council on Grants at the President of the Russian Federation (Program of State Support for Leading Scientific Schools of the Russian Federation and Young Scientists, Grant MK-3939.2014.3).
Number-of-Cited-References	23
Usage-Count-Last-180-days	1
Usage-Count-Since-2013	18
Journal-ISO	Bioorg. Med. Chem. Lett.
Doc-Delivery-Number	AL0IA