New modified 2-aminobenzimidazole nucleosides: Synthesis and evaluation of their activity against herpes simplex virus type 1 / Kharitonova Maria I.,Denisova Alexandra O.,Andronova Valeria L.,Kayushin Alexei L.,Konstantinova Irina D.,Kotovskaya Svetlana K.,Galegov Georgiy A.,Charushin Valery N.,Miroshnikov Anatoly I. // BIOORGANIC \& MEDICINAL CHEMISTRY LETTERS. - 2017. - V. 27, l. 11. - P. 2484-2487.

ISSN/EISSN:

0960-894X / 1464-3405

Type:

Article

Abstract:

Using the enzymatic transglycosylation reaction beta-D-ribo- and 2'-deoxyribofuranosides of 2-amino-5,6-difluorobenzimidazole nucleosides have been synthesized. 2-Amino-5,6-difluoro-benzimidazole riboside proved to exhibit a selective antiviral activity (selectivity index >32) against a wild strain of the herpes simplex virus type 1, as well as towards virus strains that are resistant to acyclovir, cidofovir, and foscarnet. We believe that this compound might be used for treatment of herpes infections in those cases, when acyclovir is not efficient. (C) 2017 Elsevier Ltd. All rights reserved.

Author keywords:

Nucleosides; Benzimidazoles; Fluorinated compounds; Transglycosylation reaction; Nucleoside phosphorylases; Antiviral activity CYTOMEGALOVIRUS; PHOSPHORYLASE; RIBAVIRIN; MARIBAVIR

DOI:

10.1016/j.bmc1.2017.03.100

Web of Science ID:

ISI:000402023800042

Соавторы в МНС:

Другие поля

Поле	Значение
Month	JUN 1
Publisher	PERGAMON-ELSEVIER SCIENCE LTD
Address	THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND
Language	English
EISSN	1464-3405
Keywords-Plus	CYTOMEGALOVIRUS; PHOSPHORYLASE; RIBAVIRIN; MARIBAVIR
Research-Areas	Pharmacology \& Pharmacy; Chemistry
Web-of-Science-Categories	Chemistry, Medicinal; Chemistry, Organic
Author-Email	kharitonova-mari@rambler.ru
ResearcherID-Numbers	Kharitonova, Maria/L-1594-2017 Miroshnikov, Anatoly/G-5017-2017
Funding-Acknowledgement	Ministry of Education of the Russian Federation {[}4.6351.2017/BCh]
Funding-Text	The authors are thankful to Dr. Tamara A. Balashova (Institute of Bioorganic Chemistry, Moscow) for assistance in the analysis of NMR spectra of new nucleosides, Dr. Roman S. Esipov for providing of recombinant nucleoside phosphorylases, Dr. Rashit A. Gibadulin, (DI Ivanovsky Institute of Virology, Moscow) for kindly providing the ACV/foscarnet-resistant strain of HSV-1 and the Ministry of Education of the Russian Federation (Project No 4.6351.2017/BCh) for the financial support of this work.
Number-of-Cited-References	21
Usage-Count-Last-180-days	7
Usage-Count-Since-2013	9
Journal-ISO	Bioorg. Med. Chem. Lett.
Doc-Delivery-Number	EV8IL