Synthesis and biological activity of novel 5'-arylamino-nucleosides by microwave-assisted one-pot tandem Staudinger/aza-Wittig/reduction

Hua Chen; Jianpeng Zhao; Yanan Li; Fengjuan Shen; Xiaoliu Li; Qingmei Yin; Zhanbin Qin; Xinhao Yan; Yanfei Wang; Pingzhu Zhang; Jinchao Zhang

doi:10.1016/j.bmcl.2010.10.054

Synthesis and biological activity of novel 5'-arylamino-nucleosides by microwave-assisted one-pot tandem Staudinger/aza-Wittig/reduction

Bioorg Med Chem Lett. 2011 Jan 1;21(1):574-6. doi: 10.1016/j.bmcl.2010.10.054. Epub 2010 Oct 19.

Authors

Hua Chen¹, Jianpeng Zhao, Yanan Li, Fengjuan Shen, Xiaoliu Li, Qingmei Yin, Zhanbin Qin, Xinhao Yan, Yanfei Wang, Pingzhu Zhang, Jinchao Zhang

Affiliation

¹ Key Laboratory of Chemical Biology of Hebei Province, College of Chemistry and Environmental Science, Hebei University, Baoding 071002, China.

PMID: 21095125
DOI: 10.1016/j.bmcl.2010.10.054

Abstract

Novel pseudonucleosides with benzylamino group on 5'-position (4) were synthesized by using the microwave-assisted one-pot tandem Staudinger/aza-Wittig/reduction reaction in good yields of 55.2-71.7%. The deacetylation of 4 afforded compounds 5. HIV-1 reverse transcriptase (RT) inhibitory and antitumor activities were preliminarily evaluated with 5. The results showed that the new pseudonucleosides (5) could effectively inhibit HIV-1 RT activity, but no antitumor activity.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

HIV Reverse Transcriptase / antagonists & inhibitors*
HIV Reverse Transcriptase / metabolism
Humans
Microwaves*
Nucleosides / chemical synthesis
Nucleosides / chemistry*
Nucleosides / pharmacology
Oxidation-Reduction
Reverse Transcriptase Inhibitors / chemical synthesis*
Reverse Transcriptase Inhibitors / chemistry
Reverse Transcriptase Inhibitors / pharmacology

Substances

Nucleosides
Reverse Transcriptase Inhibitors
reverse transcriptase, Human immunodeficiency virus 1
HIV Reverse Transcriptase