Journal of Integrative Natural Science (통합자연과학논문집)

The Basic Science Institute Chosun University (조선대학교 기초과학연구원)
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Design and Synthesis of Novel 2'(β)-Fluoro-3'(α)-hydroxy-threose Nucleosides: Iso-FMAU Analogues as Potent Antiviral Agents

  • Kim, Seyeon (BK-21 Project Team, College of Pharmacy, Chosun University) ;
  • Jee, Jun-Pil (BK-21 Project Team, College of Pharmacy, Chosun University) ;
  • Hong, Joon Hee (BK-21 Project Team, College of Pharmacy, Chosun University)
  • Received : 2015.04.22
  • Accepted : 2015.06.25
  • Published : 2015.06.30
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Abstract

Novel 2'(${\beta}$)-fluoro-3'(${\alpha}$)-hydroxy-threose nucleosides (iso-FMAU) as antiviral agents were designed and racemically synthesized from Solketal. Condensation successfully proceeded from a glycosyl donor 9 under $Vorbr{\ddot{u}}ggen$ conditions yielded the nucleoside analogues. Ammonolysis and hydrolysis of isopropylidene protection group gave the desired nucleoside analogues 12, 15, 18, and 19. The antiviral activities of the synthesized compounds were evaluated against the HIV-1, HSV-1, HSV-2 and HCMV. Compound 12 displayed some anti-HCMV activity ($EC_{50}=24.7{\mu}g/ml$) without exhibiting any cytotoxicity up to $100{\mu}M$.

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