Synthesis, X-ray crystal structure and antimycobacterial activity of enantiomerically pure 1-ethyl-2,3-dicyano-5-(het)aryl-6-hetaryl-1,6-dihydropyrazines / Verbitskiy Egor V.,Toporova Maria S.,Kodess Mikhail I.,Ezhikova Marina A.,Isenov Maksim L.,Pervova Marina G.,Kravchenko Marionella A.,Medvinskiy Igor D.,Skornyakov Sergey N.,Rusinov Gennady L.,Charushin Valery N. // ARKIVOC. - 2014. - V. , l. 5. - P. 247-270.

ISSN/EISSN:

1551-7004 / 1551-7012

Type:

Article

Abstract:

The Petasis reaction of 6-alkoxy adducts of 1-alkyl-2,3-dicyano-5-arylpyrazinium salts with aromatic boronic acids, such as 2-thienylboronic, 2-furanylboronic and 3-thienylboronic acids, or their benzo analogs in dichloromethane proceeds smoothly at room temperature with the formation of the corresponding 5-aryl-6-hetaryl substituted 1,6-dihydropyrazine derivatives. All dihydropyrazines were separated as pure enantiomers by chiral HPLC, and their absolute configurations for each pair of enantiomers have been determined by X-ray analysis. Individual enantiomers were screened in vitro for their antimycobacterial activities against Mycobacterium tuberculosis H(37)Rv, avium, terrae and extensively drug-resistant and multi-drug-resistant strains isolated from tuberculosis patients in Ural region (Russia). It has been shown that several compounds exhibit a good level of antituberculosis activity compared to the reference drugs.

Author keywords:

Pyrazines; Petasis reaction; antituberculosis activity; extensively drug-resistant and multi-drug-resistant tuberculosis PETASIS REACTION; BORONIC ACIDS; C-NUCLEOPHILES; 1-ETHYL-1,4-DIAZINIUM SALTS; ORGANOBORONIC ACIDS; PRACTICAL SYNTHESIS; MANNICH REACTION; O-NUCLEOPHILES; SIGMA(H)-ADDUCTS; TUBERCULOSIS

DOI:

нет данных

Web of Science ID:

ISI:000345779400017

Соавторы в МНС:

Другие поля

Поле	Значение
Publisher	ARKAT USA INC
Address	C/O ALAN R KATRITZKY, UNIV FLORIDA, DEPT CHEMISTRY, PO BOX 117200, GAINESVILLE, FL 32611 USA
Language	English
EISSN	1551-7012
Keywords-Plus	PETASIS REACTION; BORONIC ACIDS; C-NUCLEOPHILES; 1-ETHYL-1,4-DIAZINIUM SALTS; ORGANOBORONIC ACIDS; PRACTICAL SYNTHESIS; MANNICH REACTION; O-NUCLEOPHILES; SIGMA(H)-ADDUCTS; TUBERCULOSIS
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Organic
Author-Email	Verbitsky@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, 14-03-01017 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 (Grants No 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 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). Egor Verbitskiy thanks Dr. Alexey Vigorov for his personal assistance and helpful advises.
Number-of-Cited-References	54
Usage-Count-Last-180-days	1
Usage-Count-Since-2013	1
Journal-ISO	Arkivoc
Doc-Delivery-Number	AU7KM