PMID: 7543578Aug 4, 1995Paper

Anti-AIDS (acquired immune deficiency syndrome) agents. 17. New brominated hexahydroxybiphenyl derivatives as potent anti-HIV agents

Journal of Medicinal Chemistry
L XieK H Lee

Abstract

Sixteen biphenyl derivatives were synthesized and evaluated for their inhibitory activity against HIV-1 replication in acutely infected H9 cells. 3-Bromo- (4) and 3,3'-dibromo-4,4'-dimethoxy-5,6,5',6'-bis(methylenedioxy)-2,2'- bis(methoxycarbonyl)biphenyl (5) demonstrated potent anti-HIV activity with EC50 values of 0.52 and 0.23 micrograms/mL and therapeutic index values of > 190 and > 480, respectively. A comparison of the anti-HIV activity of these biphenyl derivatives suggested that the types of substituents on the phenolic hydroxy groups rather than the number of bromine(s) on the aromatic rings are important to the enhanced anti-HIV activity. Compounds 4 and 5 also showed potent inhibitory activity against HIV-1 reverse transcriptase in a template-primer dependent manner. The site of inhibition of HIV could be related to inhibition of this enzyme. Compounds 4 and 5 did not induce virus expression from the chronic HIV-1-infected cell lines ACH-2 and U1. Furthermore, these two agents did not inhibit an increase in virus production from the chronic HIV-1-infected cell lines when the phorbol ester PMA was present.

Citations

Apr 15, 2004·Bioorganic & Medicinal Chemistry Letters·Junbiao ChangKang Zhao
Aug 5, 2006·Medicinal Research Reviews·Donglei YuKuo-Hsiung Lee
May 29, 2008·Organic Letters·Xianbin SuDavid R Spring
Oct 14, 2010·Chemical Reviews·Gerhard BringmannMatthias Breuning
Oct 26, 2011·The Journal of Organic Chemistry·Noriaki AsakuraHidetoshi Yamada

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