Synthesis and anti-HCMV activity of novel cyclopropyl phosphonic acid nucleosides.
A simple synthetic route for novel acyclic phosphonate nucleosides is described. The characteristic cyclopropyl moiety 8 was constructed employing the Simmons-Smith reaction as key step starting from simple acyclic 2-butene-1,4-diol. The condensation of the mesylate 11 with natural nucleosidic bases (A,C,T,U) under nucleophilic substitution conditions (K2CO3, 18-Crown-6, DMF) and hydrolysis afforded the target nucleosides 16, 17, 18, and 19. 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
Oh
Chang Hyun
CH
D019380:Anti-HIV Agents / Q000494:pharmacology; D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D003587:Cytomegalovirus / Q000378:metabolism*; D006868:Hydrolysis; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D009705:Nucleosides / Q000737:chemistry*; D063065:Organophosphonates / Q000737:chemistry*; D010756:Phosphoric Acids / Q000737:chemistry; D010757:Phosphorous Acids / Q000737:chemistry; D011741:Pyrimidine Nucleosides / Q000737:chemistry
D019380:Anti-HIV Agents; D000998:Antiviral Agents; D009705:Nucleosides; D063065:Organophosphonates; D010756:Phosphoric Acids; D010757:Phosphorous Acids; D011741:Pyrimidine Nucleosides