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Synthesis of 2',5'-dideoxy-2-fluoroadenosine and 2',5'-dideoxy-2,5'-difluoroadenosine: potent P-site inhibitors of adenylyl cyclase.

Abstract：

:Glycosylation of 2-fluoroadenine with the appropriate protected thioglycoside derivatives, followed by deprotection and anomer separation, produced the alpha- and beta-anomers of 2',5'-dideoxy-2-fluoroadenosine (1), 2',5'-dideoxy-2,5'-difluoroadenosine (2), and 2'-deoxy-2-fluoroadenosine (3). These were examined as P-site inhibitors of adenylyl cyclase. The presence of fluorine on the purine ring increased potency of inhibition, and the most potent compound, beta-2',5'-dideoxy-2-fluoroadenosine (1b), was 3 times more potent than beta-2',5'-dideoxyadenosine.

journal_name

J Med Chem

journal_title

Journal of medicinal chemistry

authors

Ye S,Rezende MM,Deng WP,Herbert B,Daly JW,Johnson RA,Kirk KL

doi

10.1021/jm0303599

keywords:

subject

Has Abstract

pub_date

2004-02-26 00:00:00

pages

1207-13

issue

5

eissn

0022-2623

issn

1520-4804

journal_volume

47

pub_type

杂志文章

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