Synthesis and Potent Anti-HIV Activity of l-2‘,3‘-Didehydro-2‘,3‘-dideoxy-2‘-fluoro-4‘-thiocytidine

l-2‘-Fluoro-4‘-thio-2‘,3‘-unsaturated cytidine 11 was synthesized from (R)-2-fluorobutenolide 2, which was prepared from 2,3-O-isopropylidene-l-glyceraldehyde 1. The synthesized compound 11 shows potent antiviral activity against HIV-1.

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Bibliographic Details
Published in:Organic letters 2002-01, Vol.4 (2), p.305-307
Main Authors: Choi, Yongseok, Choo, Hyunah, Chong, Youhoon, Lee, Sookwang, Olgen, Sureyya, Schinazi, Raymond F, Chu, Chung K
Format: Article
Language:English
Subjects:
Anti-HIV Agents - chemical synthesis
Anti-HIV Agents - pharmacology
Cell Line - drug effects
Cytidine - analogs & derivatives
Cytidine - chemical synthesis
Cytidine - pharmacology
Dideoxynucleosides - chemical synthesis
Dideoxynucleosides - pharmacology
HIV-1 - drug effects
Humans
Inhibitory Concentration 50
Leukocytes, Mononuclear - drug effects
Thionucleosides - chemical synthesis
Thionucleosides - pharmacology
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Description
Summary:l-2‘-Fluoro-4‘-thio-2‘,3‘-unsaturated cytidine 11 was synthesized from (R)-2-fluorobutenolide 2, which was prepared from 2,3-O-isopropylidene-l-glyceraldehyde 1. The synthesized compound 11 shows potent antiviral activity against HIV-1.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol0171665