Synthesis and antiviral evaluation of novel methyl branched cyclopropyl phosphonic acid nucleosides.
A simple synthetic route for the synthesis of novel methyl branched cyclopropyl phosphonic acid nucleosides is described. The characteristic cyclopropyl moiety 8 was constructed by employing Simmons-Smith reaction as a key step. The condensation of mesylate 11 with natural nucleosidic bases (A,C,T,U) under standard nucleophilic substitution conditions (K2CO3, 18-Crown-6, DMF) and after subsequent hydrolysis resulted in the formation of target nucleosides, 16, 17, 18, and 19. In addition, the antiviral evaluations of the synthesized nucleotides against various viruses were also performed.
Kim
Jin Woo
JW
College of Pharmacy, Chosun University, Kwangju 501-759, Korea.
Ko
Ok Hyun
OH
Hong
Joon Hee
JH
D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D003521:Cyclopropanes / Q000737:chemistry; D015497:HIV-1 / Q000187:drug effects; D008745:Methylation; D008826:Microbial Sensitivity Tests; D009705:Nucleosides / Q000138:chemical synthesis* / Q000494:pharmacology
D000998:Antiviral Agents; D003521:Cyclopropanes; D009705:Nucleosides