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Synthesis and anti-HIV activity of 4'-cyano-2',3'-didehydro-3'-deoxythymidine. 2004
Kazuhiro Haraguchi, and
Yoshiharu Itoh, and
Shingo Takeda, and
Yosuke Honma, and
Hiromichi Tanaka, and
Takao Nitanda, and
Masanori Baba, and
Ginger E Dutschman, and
Yung-Chi Cheng
School of Pharmaceutical Sciences, Showa University, Shinagawa-ku, Tokyo, Japan. harakazu@pharm.showa-u.ac.jp
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).
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