title: Synthesis and antiviral activity of fluoro-substituted apio dideoxynucleosides.
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.
authors.affiliation: Laboratory of Medicinal Chemistry, College of Pharmacy, Ewha Womans University, Seoul, Korea.
authors.forename: J H
authors.initials: JH
authors.lastname: Hong
authors.forename: H O
authors.initials: HO
authors.lastname: Kim
authors.forename: H R
authors.initials: HR
authors.lastname: Moon
authors.forename: L S
authors.initials: LS
authors.lastname: Jeong
mesh_terms: D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D015224:Dideoxynucleosides / Q000138:chemical synthesis* / Q000494:pharmacology*; D009682:Magnetic Resonance Spectroscopy; D008826:Microbial Sensitivity Tests; D013056:Spectrophotometry, Ultraviolet; D014780:Viruses / Q000187:drug effects
chemical_list: D000998:Antiviral Agents; D015224:Dideoxynucleosides