Synthesis of novel carboacyclic nucleosides with vinyl bromide moiety as open-chain analogues of neplanocin A
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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.
Key wordsCarboacyclic nucleoside Neplanocin A Antiviral Open-chain analog
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