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Issue 9, 2016
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Synthetic α-hydroxytropolones as inhibitors of HIV reverse transcriptase ribonuclease H activity

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Abstract

HIV reverse transcriptase-associated ribonuclease H activity is a promising enzymatic target for drug development that has not been successfully targeted in the clinic. While the α-hydroxytropolone-containing natural products β-thujaplicinol and manicol have emerged as some of the most potent leads described to date, structure–function studies have been limited to the natural products and semi-synthetic derivatives of manicol. Thus, a library of α-hydroxytropolones synthesized through a convenient oxidopyrylium cycloaddition/ring-opening sequence have been tested in in vitro and cell-based assays, and have been analyzed using computational support. These studies reveal new synthetic α-hydroxytropolones that, unlike the natural product leads they are derived from, demonstrate protective antiviral activity in cellular assays.

Graphical abstract: Synthetic α-hydroxytropolones as inhibitors of HIV reverse transcriptase ribonuclease H activity

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Supplementary files

Article information


Submitted
28 Apr 2016
Accepted
05 Jul 2016
First published
07 Jul 2016

Med. Chem. Commun., 2016,7, 1783-1788
Article type
Research Article
Author version available

Synthetic α-hydroxytropolones as inhibitors of HIV reverse transcriptase ribonuclease H activity

R. P. Murelli, M. P. D'Erasmo, D. R. Hirsch, C. Meck, T. Masaoka, J. A. Wilson, B. Zhang, R. K. Pal, E. Gallicchio, J. A. Beutler and S. F. J. Le Grice, Med. Chem. Commun., 2016, 7, 1783
DOI: 10.1039/C6MD00238B

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