Synthesis, antimycobacterial and antifungal evaluation of some new 1-ethyl-5-(hetero)aryl-6-styryl-1,6-dihydropyrazine-2,3-dicarbonitriles / Verbitskiy Egor V.,Slepukhin Pavel A.,Kravchenko Marionella A.,Skornyakov Sergey N.,Evstigneeva Natal'ya P.,Kungurov Nikolay V.,Zil'berberg Natal'ya V.,Rusinov Gennady L.,Chupakhin Oleg N.,Charushin Valery N. // BIOORGANIC \& MEDICINAL CHEMISTRY LETTERS. - 2015. - V. 25, l. 3. - P. 524-528.

ISSN/EISSN:

0960-894X / 1464-3405

Type:

Article

Abstract:

The Petasis reaction of 6-hydroxy adducts of 1-alkyl-2,3-dicyano-5-arylpyrazinium salts with trans-styrylboronic acids proved to proceed smoothly at room temperature to give the corresponding 5-(hetero)aryl-6-styryl substituted 1,6-dihydropyrazine derivatives. Also it has been found that C(6) unsubstituted 1,6-dihydro- or 1,4,5,6-tetrahydropyrazine derivatives can be easy prepared in high yields from the corresponding pyrazinium salts by reduction with triethylsilane. All synthesized compounds were screened in vitro for their antifungal activities against seven pathogenic fungal strains and antimycobacterial activities against Mycobacterium tuberculosis H(37)Rv, avium, terrae and multi-drug-resistant strains isolated from tuberculosis patients in the Ural region (Russia). (C) 2014 Elsevier Ltd. All rights reserved.

Author keywords:

Pyrazine; Petasis reaction; Antituberculosis activity; Antifungal activity; Tuberculosis SUBSTITUTED PYRAZINECARBOXAMIDES; BIOLOGICAL EVALUATION; DERIVATIVES; ACIDS

DOI:

10.1016/j.bmcl.2014.12.025

Web of Science ID:

ISI:000347901700019

Соавторы в МНС:

Другие поля

Поле	Значение
Month	FEB 1
Publisher	PERGAMON-ELSEVIER SCIENCE LTD
Address	THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND
Language	English
EISSN	1464-3405
Keywords-Plus	SUBSTITUTED PYRAZINECARBOXAMIDES; BIOLOGICAL EVALUATION; DERIVATIVES; ACIDS
Research-Areas	Pharmacology \& Pharmacy; Chemistry
Web-of-Science-Categories	Chemistry, Medicinal; Chemistry, Organic
Funding-Acknowledgement	Ural Branch of the Russian Academy of Sciences {[}13-3-019-UMA]; Russian Foundation for Basic Research {[}13-03-96049- r\_ural\_a, 13-03-90606-Arm\_a, 14-03-01017 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 (Grant No 13-3-019-UMA), the Russian Foundation for Basic Research (research projects No. 13-03-96049- r\_ural\_a, 13-03-90606-Arm\_a, 14-03-01017 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). The authors thank Mariya S. Toporova for performing HPLC analyses and Dr. Marina G. Pervova for performing GS-MS analyses. The authors express their gratitude to M. L. Isenov for carrying the X-ray structural analysis of one of the compounds. Egor Verbitskiy thanks Dr. Alexey Vigorov for his personal assistance and helpful advises.
Number-of-Cited-References	16
Usage-Count-Last-180-days	1
Usage-Count-Since-2013	17
Journal-ISO	Bioorg. Med. Chem. Lett.
Doc-Delivery-Number	AY9XT