1. Synthesis and anti-HIV activity of 4'-cyano-2',3'-didehydro-3'-deoxythymidine
- Author
-
Ginger E. Dutschman, Yoshiharu Itoh, Masanori Baba, Kazuhiro Haraguchi, Yung-Chi Cheng, Hiromichi Tanaka, Yosuke Honma, Shingo Takeda, and Takao Nitanda
- Subjects
Anti hiv activity ,Allylic rearrangement ,Stereochemistry ,Anti hiv ,Chemistry ,Anti-HIV Agents ,Leaving group ,HIV Infections ,General Medicine ,Biochemistry ,chemistry.chemical_compound ,Stavudine ,Nucleic acid ,Genetics ,HIV-1 ,Molecular Medicine ,Animals ,Humans ,Thymidine ,Nucleoside - Abstract
A new anti‐HIV agent 4′‐cyano‐2′,3′‐didehydro‐3′‐deoxythymidine (9) was synthesized by allylic substitution of the 3′,4′‐unsaturated nucleoside 14, having a leaving group at the 2′‐position, with cyanotrimethylsilane in the presence of SnCl4. Evaluation of the anti‐HIV activity of 9 showed that this compound is much less potent than the recently reported 2′,3′‐didehydro‐3′‐deoxy‐4′‐(ethynyl)thymidine (1).
- Published
- 2004