title: Synthesis and antiviral evaluation of (+/-)-4'-ethynyl-5'-difluorocarbocyclic-d4T analogue.
abstract: Synthesis of (+/-)-4'-ethynyl-5'-difluorocarbocyclic-d4T analogue 8, in which the furanose ring oxygen of usual nucleosides is replaced with a geminal-difluoromethylidene group, was carried out. Electrophilic fluorination with Selectfluor was applied to construct a gem-difluorocyclopentenone system to give 12. Regioselective introduction of thymine base was performed under the Mitsunobu conditions by employing the 4-methoxycarbonyl derivative 13. Antiviral evaluation of 8 was also examined.
authors.affiliation: School of Pharmaceutical Sciences, Showa University, 1-5-8 Hatanodai, Shinagawa-ku, Tokyo 142-8555, Japan. kumamoto@pharm.showa-u.ac.jp
authors.forename: Hiroki
authors.initials: H
authors.lastname: Kumamoto
authors.forename: Kazuhiro
authors.initials: K
authors.lastname: Haraguchi
authors.forename: Mayumi
authors.initials: M
authors.lastname: Ida
authors.forename: Hiromichi
authors.initials: H
authors.lastname: Tanaka
authors.forename: Takayuki
authors.initials: T
authors.lastname: Hamasaki
authors.forename: Masanori
authors.initials: M
authors.lastname: Baba
mesh_terms: D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D003517:Cyclopentanes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013936:Thymidine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology
chemical_list: D000998:Antiviral Agents; D003517:Cyclopentanes; D013936:Thymidine