Synthesis of novel carboacyclic nucleosides with vinyl bromide moiety as open-chain analogues of neplanocin A.
A novel carboacyclic nucleoside analogue, 9-[2-bromo-4-hydroxy-3-hydroxymethyl-2-butenyl] adenine, and its derivatives were designed and synthesized as open-chain analogues of neplanocin A. The syntheses were accomplished via the coupling of adenine or pyrimidine bases to the key intermediate allylic bromide 7. The bromide 7 was prepared from epichlorohydrin in a seven step process in a 54% overall yield. The synthesized compounds were evaluated for their antiviral activity against the polio virus, HSV and HIV.
Choi
Myung-Hee
MH
College of Pharmacy, Sookmyung Women's University, Seoul 140-742, Korea.
Kim
Hee-Doo
HD
D000241:Adenosine / Q000031:analogs & derivatives / Q000138:chemical synthesis*; D009705:Nucleosides / Q000138:chemical synthesis*; D014753:Vinyl Compounds / Q000138:chemical synthesis*
D009705:Nucleosides; D014753:Vinyl Compounds; C031096:neplanocin A; C003763:vinyl bromide; D000241:Adenosine