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Synthesis of Novel Carboacyclic Nucleosides with Vinyl Bromide Moiety as Open-chain Analogues of Neplanocin A  

Choi, Myung-Hee (College of Pharmacy, Sookmyung Women s University)
Kim, Hee-Doo (College of Pharmacy, Sookmyung Women s University)
Publication Information
Archives of Pharmacal Research / v.26, no.12, 2003 , pp. 990-996 More about this Journal
Abstract
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.
Keywords
Carboacyclic nucleoside; Neplanocin A; Antiviral; Open-chain analog;
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Times Cited By Web Of Science : 2  (Related Records In Web of Science)
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