Synthesis of (+/-)-4'-ethynyl and 4'-cyano carbocyclic analogues of stavudine (d4T).
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.
Kumamoto
Hiroki
H
School of Pharmaceutical Sciences, Showa University, Tokyo, Japan. kumamoto@pharm.showa-u.ac.jp
Haraguchi
Kazuhiro
K
Tanaka
Hiromichi
H
Nitanda
Takao
T
Baba
Masanori
M
Dutschman
Ginger E
GE
Cheng
Yung-Chi
YC
Kato
Keisuke
K
D015394:Molecular Structure; D018119:Stavudine / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry
D018119:Stavudine