title: Synthesis and anti-HIV activity of 4'-cyano-2',3'-didehydro-3'-deoxythymidine.
abstract: 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).
authors.affiliation: School of Pharmaceutical Sciences, Showa University, Shinagawa-ku, Tokyo, Japan. harakazu@pharm.showa-u.ac.jp
authors.forename: Kazuhiro
authors.initials: K
authors.lastname: Haraguchi
authors.forename: Yoshiharu
authors.initials: Y
authors.lastname: Itoh
authors.forename: Shingo
authors.initials: S
authors.lastname: Takeda
authors.forename: Yosuke
authors.initials: Y
authors.lastname: Honma
authors.forename: Hiromichi
authors.initials: H
authors.lastname: Tanaka
authors.forename: Takao
authors.initials: T
authors.lastname: Nitanda
authors.forename: Masanori
authors.initials: M
authors.lastname: Baba
authors.forename: Ginger E
authors.initials: GE
authors.lastname: Dutschman
authors.forename: Yung-Chi
authors.initials: YC
authors.lastname: Cheng
mesh_terms: 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
chemical_list: C496132:4'-cyano-2',3'-didehydro-3'-deoxythymidine; D019380:Anti-HIV Agents; D018119:Stavudine; D013936:Thymidine