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Synthesis of novel carboacyclic nucleosides with vinyl bromide moiety as open-chain analogues of neplanocin A

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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.

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Correspondence to Myung-Hee Choi or Hee-Doo Kim.

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Choi, M., Kim, H. Synthesis of novel carboacyclic nucleosides with vinyl bromide moiety as open-chain analogues of neplanocin A. Arch Pharm Res 26, 990–996 (2003). https://doi.org/10.1007/BF02994747

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Key words

  • Carboacyclic nucleoside
  • Neplanocin A
  • Antiviral
  • Open-chain analog