title: Synthesis of 5-thiodidehydropyranylcytosine derivatives as potential anti-HIV agents.
abstract: As a part of our ongoing efforts to identify new anti-HIV agents, a 5'-thiopyrano-nucleoside derivative 4, designed based on 4'-thioD4C 1 and cyclohexenylnucleoside 3, was synthesized. The dihydrothiopyran skeleton of 4 was constructed by the ring closing metathesis of 21 which was synthesized from but-2-yne-1,4-diol. After converting the protecting group from MOM to TBS followed by oxidation, a Pummerer-type thioglycosylation reaction of 24 with persilylated uracil gave the desired 5-thiodihydrothiopyranyluracils 25 and 26 as a mixture of anomers. The conversion of 25 to a cytosine derivative and subsequent deprotection gave a 5-thiodidehydropyranosylcytosine derivative 4 in good yield. The anti-HIV activity of 4 was also evaluated.
authors.affiliation: Faculty of Pharmaceutical Sciences, Tohoku Pharmaceutical University, 4-4-1 Komatsushima, Aoba-ku, Sendai 981-8558, Japan. yoshimura@tohoku-pharm.ac.jp
authors.forename: Yuichi
authors.initials: Y
authors.lastname: Yoshimura
authors.forename: Yoshiko
authors.initials: Y
authors.lastname: Yamazaki
authors.forename: Yukako
authors.initials: Y
authors.lastname: Saito
authors.forename: Yoshihiro
authors.initials: Y
authors.lastname: Natori
authors.forename: Tomozumi
authors.initials: T
authors.lastname: Imamichi
authors.forename: Hiroki
authors.initials: H
authors.lastname: Takahata
mesh_terms: D019380:Anti-HIV Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D003596:Cytosine / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D015497:HIV-1 / Q000187:drug effects*; D006801:Humans; D015394:Molecular Structure; D011714:Pyrans / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D013457:Sulfur Compounds / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D014779:Virus Replication / Q000187:drug effects
chemical_list: D019380:Anti-HIV Agents; D011714:Pyrans; D013457:Sulfur Compounds; D003596:Cytosine