Simple synthesis and anti-HIV activity of novel cyclopentene phosphonate nucleosides.
A very simple synthetic route for novel cyclopentene phosphonate nucleosides is described. The characteristic cyclopentene moiety 6 was constructed via a ring-closing metathesis of divinyl 5, which could be readily prepared from diethylmalonate. The condensation of the mesylate 11 with nucleobases (A, C, T, U) under nucleophilic substitution conditions (K2CO3, 18-Crown-6, DMF) afforded the target nucleosides 12, 13, 14, and 15. In addition, the antiviral evaluations against various viruses were performed.
Kim
Aihong
A
College of Pharmacy, Chosun University, Kwangju, Republic of Korea.
Hong
Joon Hee
JH
D000475:Alkenes / Q000737:chemistry*; D019380:Anti-HIV Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D003500:Cyclization; D015195:Drug Design; D015497:HIV-1 / Q000187:drug effects*; D018259:Herpesvirus 1, Human / Q000187:drug effects; D018258:Herpesvirus 2, Human / Q000187:drug effects; D015394:Molecular Structure; D009705:Nucleosides / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D010766:Phosphorylation
D000475:Alkenes; D019380:Anti-HIV Agents; D009705:Nucleosides