Synthesis of acyclic nucleoside analogues based on 1,2,4-triazolo {[}1,5-a]pyrimidin-7-ones by one-step Vorbruggen glycosylation / Khalymbadzha Igor A.,Shestakova Tatyana S.,Subbotina Julia O.,Eltsov Oleg S.,Musikhina Alexandra A.,Rusinov Vladimir L.,Chupakhin Oleg N.,Karpenko Inna L.,Jasko Maxim V.,Kukhanova Marina K.,Deev Sergey L. // TETRAHEDRON. - 2014. - V. 70, l. 6. - P. 1298-1305.

ISSN/EISSN:

0040-4020 / нет данных

Type:

Article

Abstract:

New acyclovir analogues were obtained by reaction of 1,2,4-triazolo{[}1,5-a]pyrimidin-7-ones 4a-i with (2-acetoxyethoxy)methyl acetate 5 in the presence of trimethylsilyl trifluoromethanesulfonate (TMSOTf) as catalyst (Vorbruggen procedure). Coupling between compounds 4a-f and 5 led to a mixture of N3- and N4-isomers 6 and 7, respectively. On the contrary, the reaction of compounds 4g-i with 5 proceeded selectively with formation of N3-isomers only. It was found that the ratio of 6a-f and 7a-f depends on the presence or the absence of N,O-bis(trimethylsilyl)acetamide (BSA). Glycosylated products 6a-f and 7a-f underwent reversible isomerization under TMSOTf treatment. The ratio of glycosylated products of the coupling reaction between 4 and 5 was thermodynamically controlled. A similar reaction occurred if ZnCl2 was chosen as a catalyst, although lower yields of the acyclic analogues of nucleosides were observed. The glycosylation of other purines (adenine and guanine) can be achieved via the non-BSA modification of the Vorbruggen procedure. Crown Copyright (C) 2014 Published by Elsevier Ltd. All rights reserved.

Author keywords:

Acyclovir analogues; 1,2,4-Triazolo{[}1,5-a]pyrimidine-7-one; TMSOTf; Vorbruggen glycosylation; Herpes simplex virus; Regioselectivity; Transglycosylation FALCIPARUM DIHYDROOROTATE DEHYDROGENASE; INHIBITORS; POTENT; VIRUS; ACYCLONUCLEOSIDES; DERIVATIVES; CONVENIENT; GUANOSINE; DESIGN; DRUGS

DOI:

10.1016/j.tet.2013.12.051

Web of Science ID:

ISI:000330920500024

Соавторы в МНС:

Другие поля

Поле	Значение
Month	FEB 11
Publisher	PERGAMON-ELSEVIER SCIENCE LTD
Address	THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND
Language	English
Keywords-Plus	FALCIPARUM DIHYDROOROTATE DEHYDROGENASE; INHIBITORS; POTENT; VIRUS; ACYCLONUCLEOSIDES; DERIVATIVES; CONVENIENT; GUANOSINE; DESIGN; DRUGS
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Organic
Author-Email	deevsl@yandex.ru
ResearcherID-Numbers	Karpenko, Inna/F-5879-2015 Subbotina, Julia/L-7131-2016
ORCID-Numbers	Karpenko, Inna/0000-0001-9849-0447 Subbotina, Julia/0000-0002-2227-0787
Funding-Acknowledgement	Federal Target Program Scientific and Science-Educational Personnel of Innovative Russia' {[}14.A18.21.0806]; Russian Foundation for Basic Research {[}13-04-02059, 12-03-33144, 12-03-31476, 12-04-00581]
Funding-Text	This work was supported by the Federal Target Program Scientific and Science-Educational Personnel of Innovative Russia' (State contract 14.A18.21.0806) and Russian Foundation for Basic Research (projects 13-04-02059, 12-03-33144, 12-03-31476, and 12-04-00581). J.O.S thanks Compute Canada-Calcul Canada and West Grid for computing resources and Prof. Arvi Rauk (University of Calgary, Canada) for his personal assistance.
Number-of-Cited-References	50
Usage-Count-Last-180-days	3
Usage-Count-Since-2013	33
Journal-ISO	Tetrahedron
Doc-Delivery-Number	AA2JI