Synthesis of a highly active new anti-HIV agent 2',3'-didehydro-3'-deoxy-4'-ethynylthymidine.
Compounds having methyl, vinyl, and ethynyl groups at the 4'-position of stavudine (d4T: 2',3'-didehydro-3'-deoxythymidine) were synthesized. The compounds were assayed for their ability to inhibit the replication of HIV in cell culture. The 4'-ethynyl analogue (15) was found to be more potent and less toxic than the parent compound stavudine.
Haraguchi
Kazuhiro
K
School of Pharmaceutical Sciences, Showa University, 1-5-8 Hatanodai, Shinagawa-ku, Tokyo 142-8555, Japan.
Takeda
Shingo
S
Tanaka
Hiromichi
H
Nitanda
Takao
T
Baba
Masanori
M
Dutschman
G E
GE
Cheng
Yung-Chi
YC
D019380:Anti-HIV Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D002478:Cells, Cultured; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D018119:Stavudine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D013329:Structure-Activity Relationship; D014779:Virus Replication / Q000187:drug effects
D019380:Anti-HIV Agents; C486840:2',3'-didehydro-3'-deoxy-4'-ethynylthymidine; D018119:Stavudine