title: Synthesis of 4-methylthio analogues of FLT and AZT and their evaluation against HIV.
abstract: Silylated 4-methylthiouracil and 4-methylthiothymine were condensed in the presence of TMS triflate with methyl 2,3-dideoxy-3-fluoro-5-O-(4- phenylbenzoyl)-D-erythro-pentofuranoside (3) and methyl 3-azido-5-O- (tert-butyldiphenylsilyl)-2,3-dideoxy-D-erythro-pentofuroside++ + (8), respectively, to give the corresponding nucleosides which were deprotected. The 3'-azido nucleoside was reduced with triphenylphosphine to the corresponding 3'-amino nucleoside. The 3'-amino nucleoside was also obtained by condensation of 4-methylthiothymidine with a 3-phthalimido sugar 14 followed by deprotection. The 4-methylthio analogue 11 of AZT showed moderate activity against HIV.
authors.affiliation: Department of Chemistry, Odense University, Denmark.
authors.forename: A A
authors.initials: AA
authors.lastname: Abel-Rahman
authors.forename: H M
authors.initials: HM
authors.lastname: Abdel-Bary
authors.forename: E B
authors.initials: EB
authors.lastname: Pedersen
authors.forename: C
authors.initials: C
authors.lastname: Nielsen
mesh_terms: D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D015224:Dideoxynucleosides / Q000138:chemical synthesis* / Q000494:pharmacology; D015497:HIV-1 / Q000187:drug effects*; D015215:Zidovudine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000494:pharmacology
chemical_list: D000998:Antiviral Agents; D015224:Dideoxynucleosides; D015215:Zidovudine; C002854:alovudine