title: Synthesis of (+/-)-4'-ethynyl and 4'-cyano carbocyclic analogues of stavudine (d4T).
abstract: The synthesis of (+/-)-4'-ethynyl (8) and 4'-cyano (9) carbocyclic analogues of the anti-HIV agent stavudine (5, d4T) is reported. The carbocyclic unit (16) was constructed from readily available beta-keto ester 10. The ethynyl or cyano group of 8 and 9 were prepared, after the introduction of thymine base to 16, by manipulation of the ester function. Evaluation of the anti-HIV activity of 8 and 9 was also carried out.
authors.affiliation: School of Pharmaceutical Sciences, Showa University, Tokyo, 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: Hiromichi
authors.initials: H
authors.lastname: Tanaka
authors.forename: Takao
authors.initials: T
authors.lastname: Nitanda
authors.forename: Masanori
authors.initials: M
authors.lastname: Baba
authors.forename: Ginger E
authors.initials: GE
authors.lastname: Dutschman
authors.forename: Yung-Chi
authors.initials: YC
authors.lastname: Cheng
authors.forename: Keisuke
authors.initials: K
authors.lastname: Kato
mesh_terms: D015394:Molecular Structure; D018119:Stavudine / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D018119:Stavudine