Synthesis and antiviral evaluation of novel exomethylene acyclic nucleosides and phosphonic acid nucleosides.
This paper describes a very simple synthesis route of novel acyclic nucleosides and phosphonic acid nucleosides. The condensation of the mesylates 6 and 17 with the natural nucleosidic bases (A, C, U, T) under nucleophilic substitution (K(2)CO(3), 18-Crown-6, DMF) and deprotection afforded the target nucleosides (11, 12, 13, 14) and phosphonic acid nucleosides (22, 23, 24, 25). In addition, these compounds were evaluated for their antiviral properties against various viruses. Uracil derivative 24 shows significant anti-HCMV activity (EC(50) = 10.24 microM).
Kim
Aihong
A
College of Pharmacy, Chosun University, Kwangju, Republic of Korea.
Hong
Joon Hee
JH
D000998:Antiviral Agents / Q000009:adverse effects / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D002460:Cell Line; D002470:Cell Survival / Q000187:drug effects; D003587:Cytomegalovirus / Q000187:drug effects; D006801:Humans; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D015394:Molecular Structure; D009705:Nucleosides / Q000009:adverse effects / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D063065:Organophosphonates / Q000737:chemistry*; D013329:Structure-Activity Relationship
D000998:Antiviral Agents; D009705:Nucleosides; D063065:Organophosphonates; C504223:methylene radical; D008697:Methane