Literature DB >> 15200028

Synthesis and anti-HIV activity of 4'-cyano-2',3'-didehydro-3'-deoxythymidine.

Kazuhiro Haraguchi1, Yoshiharu Itoh, Shingo Takeda, Yosuke Honma, Hiromichi Tanaka, Takao Nitanda, Masanori Baba, Ginger E Dutschman, Yung-Chi Cheng.   

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).

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Year:  2004        PMID： 15200028     DOI： 10.1081/NCN-120030721

Source DB:  PubMed          Journal:  Nucleosides Nucleotides Nucleic Acids        ISSN： 1525-7770            Impact factor:   1.381


  3 in total

Review 1.  From the chemistry of epoxy-sugar nucleosides to the discovery of anti-HIV agent 4'-ethynylstavudine-Festinavir.

Authors:  Kazuhiro Haraguchi; Shingo Takeda; Yutaka Kubota; Hiroki Kumamoto; Hiromichi Tanaka; Takayuki Hamasaki; Masanori Baba; Elijah Paintsil; Yung-Chi Cheng
Journal:  Curr Pharm Des       Date:  2013       Impact factor: 3.116

2.  Anti-human immunodeficiency virus type 1 activity and resistance profile of 2',3'-didehydro-3'-deoxy-4'-ethynylthymidine in vitro.

Authors:  Takao Nitanda; Xin Wang; Hiroki Kumamoto; Kazuhiro Haraguchi; Hiromichi Tanaka; Yung-Chi Cheng; Masanori Baba
Journal:  Antimicrob Agents Chemother       Date:  2005-08       Impact factor: 5.191

3.  Comparison of the phosphorylation of 4'-ethynyl 2',3'-dihydro-3'-deoxythymidine with that of other anti-human immunodeficiency virus thymidine analogs.

Authors:  Chih-Hung Hsu; Rong Hu; Ginger E Dutschman; Guangwei Yang; Preethi Krishnan; Hiromichi Tanaka; Masanori Baba; Yung-Chi Cheng
Journal:  Antimicrob Agents Chemother       Date:  2007-03-12       Impact factor: 5.191
  3 in total

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