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Current Medicinal Chemistry

Editor-in-Chief

ISSN (Print): 0929-8673
ISSN (Online): 1875-533X

Synthesis and HIV-1 Inhibitory Activities of Dicaffeoyl and Digalloyl Esters of Quinic Acid Derivatives

Author(s): C. O.R. Junior, S. C. Verde, C. A.M. Rezende, W. Caneschi, M. R.C. Couri, B. R. McDougall, W. E. Robinson, Jr. and M. V. de Almeida

Volume 20 , Issue 5 , 2013

Page: [724 - 733] Pages: 10

DOI: 10.2174/092986713804999349

Price: $65

Abstract

Twenty analogues of the anti-HIV-1 integrase (IN) inhibitors dicaffeoylquinic acids (DCQAs) were prepared. Their IC50 values for 3’-end processing and strand transfer against recombinant HIV-1IN were determined in vitro, and their cell toxicities and EC50 against HIV-1 were measured in cells (ex vivo). Acetylated or benzylated and/or with cyclohexylidene group compounds exhibited no inhibition of integration in biochemical assays or viral replication in HIV-infected cells, with the exception of 16 and 36. Removal of these groups, however, correlated with potent inhibition. Compounds 19, 31, and 38, all digalloyls, exhibited the most robust inhibitory performance in biochemical assays as well as in cell culture and less toxicity than other molecules in the current study.

Keywords: Integrase inhibitor, HIV-1, dicaffeoyl, digalloyl, second generation inhibitor, esters, quinic acid, cyclitol, anti-HIV agents, catechol.


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