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Fluorinated sugar analogues of potential anti-HIV-1 nucleosides.

Abstract：

:In order to obtain agents with therapeutic indices superior to those of AZT, FLT, or D4T, several analogues of anti-HIV-1 nucleosides were synthesized. These include 2',3'-dideoxy-2',3' -difluoro-5-methyluridine (13), its arabino analogue 19, arabino-5-methylcytosine analogue 21, 3'-deoxy-2',3'-didehydro-2' -fluorothymidine (25), 3'-azido-2',3'-dideoxy-2'-fluoro-5-methyluridine (29), 2'-azido-3'-fluoro-2',3'-dideoxy-5-methyluridine (31), and 2'3'-dideoxy-2' -fluoro-5-methyluridine (37). These new nucleosides were screened for their activity against HIV and feline TLV in vitro. None of the compounds showed significant activity. It is interesting to note that such a small modification in the sugar moiety of active anti-HIV nucleosides (i.e., displacement of hydrogen by fluorine) almost completely inactivate the agents.

journal_name

J Med Chem

journal_title

Journal of medicinal chemistry

authors

Huang JT,Chen LC,Wang LB,Kim MH,Warshaw JA,Armstrong D,Zhu QY,Chou TC,Watanabe KA,Matulic-Adamic J

doi

10.1021/jm00109a017

subject

Has Abstract,Author List Incomplete

pub_date

1991-05-01 00:00:00

pages

1640-6

issue

5

eissn

0022-2623

issn

1520-4804

journal_volume

34

pub_type

杂志文章

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