Synthesis and anti-HIV activity of 4'-cyano-2',3'-didehydro-3'-deoxythymidine.
A new anti-HIV agent 4'-cyano-2',3'-didehydro-3'-deoxythymidine (9) was synthesized by allylic substitution of the 3',4'-unsaturated nucleoside 14, having a leaving group at the 2'-position, with cyanotrimethylsilane in the presence of SnCl4. Evaluation of the anti-HIV activity of 9 showed that this compound is much less potent than the recently reported 2',3'-didehydro-3'-deoxy-4'-(ethynyl)thymidine (1).
Haraguchi
Kazuhiro
K
School of Pharmaceutical Sciences, Showa University, Shinagawa-ku, Tokyo, Japan. harakazu@pharm.showa-u.ac.jp
Itoh
Yoshiharu
Y
Takeda
Shingo
S
Honma
Yosuke
Y
Tanaka
Hiromichi
H
Nitanda
Takao
T
Baba
Masanori
M
Dutschman
Ginger E
GE
Cheng
Yung-Chi
YC
D000818:Animals; D019380:Anti-HIV Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D015658:HIV Infections / Q000188:drug therapy; D015497:HIV-1 / Q000187:drug effects; D006801:Humans; D018119:Stavudine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D013936:Thymidine / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology
C496132:4'-cyano-2',3'-didehydro-3'-deoxythymidine; D019380:Anti-HIV Agents; D018119:Stavudine; D013936:Thymidine