Synthesis and antiviral activity of fluoro-substituted apio dideoxynucleosides

Archives of Pharmacal Research
J H HongL S Jeong

Abstract

Novel fluoro-substituted apio dideoxynucleosides ((+/-)-3a and (+/-)-3b) were efficiently synthesized starting from 1,3-dihydroxyacetone via Horner-Emmons olefination as a key step. Cyclization of fluoro ester (+/-)-6 under acidic conditions to the fluorolactone was smoothly proceeded in favor of trans-fluorolactone due to the favorable transition state with equatorial hydroxymethyl substituent. Unfortunately, the final nucleosides (+/-)-3a and (+/-)-3b were found to be inactive against several viruses such as HIV-1, HSV-1, HSV-2 and HCMV.

Citations

May 5, 2007·Nucleosides, Nucleotides & Nucleic Acids·Chang Hyun Oh, Joon Hee Hong
Sep 27, 2015·Nucleosides, Nucleotides & Nucleic Acids·Seyeon Kim, Joon Hee Hong
Feb 26, 2004·Bioorganic & Medicinal Chemistry·Dong Zhe JinLak Shin Jeong
Apr 26, 2006·Journal of Clinical Pharmacy and Therapeutics·R B RaffaH-F Jen Weng
Oct 24, 2019·Drug Development Research·Balija SivakrishnaShantanu Pal

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