Synthesis and anti-HIV activity of 4'-thio-2',3'-dideoxynucleosides

A series of 2',3'-dideoxy-4'-thionucleoside analogues of purines and pyrimidines, including 4'-thioddI (17), 4'-thioddC (27), and 4'-thioAZT (34), were synthesized and evaluated for their inhibitory activity against human immunodeficiency virus (HIV). A stereospecific s...

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Bibliographic Details
Published in:	Journal of medicinal chemistry Vol. 35; no. 3; pp. 533 - 538
Main Authors:	Secrist, John A, Riggs, Robert M, Tiwari, Kamal N, Montgomery, John A
Format:	Journal Article
Language:	English
Published:	United States American Chemical Society 01-02-1992
Subjects:	AIDS/HIV Antiviral Agents - chemical synthesis Antiviral Agents - pharmacology Dideoxynucleosides - chemical synthesis Dideoxynucleosides - pharmacology HIV - drug effects human immunodeficiency virus
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Summary:	A series of 2',3'-dideoxy-4'-thionucleoside analogues of purines and pyrimidines, including 4'-thioddI (17), 4'-thioddC (27), and 4'-thioAZT (34), were synthesized and evaluated for their inhibitory activity against human immunodeficiency virus (HIV). A stereospecific synthesis of the 2,3-dideoxy-4-thioribofuranosyl carbohydrate precursor 11 starting with L-glutamic acid is described. 2',3'-Dideoxy-4'-thiocytidine (27) displayed significant, but modest activity in vitro against human immunodeficiency virus.
Bibliography:	istex:CB1300F06A13A89280BE1C43A212467BA3B31265 ark:/67375/TPS-KF473W2C-H ObjectType-Article-2 SourceType-Scholarly Journals-1 ObjectType-Feature-1 content type line 23 ObjectType-Article-1 ObjectType-Feature-2
ISSN:	0022-2623 1520-4804
DOI:	10.1021/jm00081a015