Journal
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
Volume 92, Issue -, Pages 656-671Publisher
ELSEVIER FRANCE-EDITIONS SCIENTIFIQUES MEDICALES ELSEVIER
DOI: 10.1016/j.ejmech.2015.01.033
Keywords
Antiviral agents; AIDS; HIV; HCV; Polyphenols
Categories
Funding
- KU Leuven [GOA 10/14, PF 10/18]
- FWO [G-0528.12N]
- Spanish MICINN/MINECO [SAF 2012-39760-C02-01]
- FEDER
- Spanish MICINN/MINECO (Plan Nacional de Cooperacion Publico-Privada)
- Subprograma INNPACTO [IPT-2012-0213-060000]
- Comunidad de Madrid [BIPEDD2-CM-S2010/BMD-2457]
- Spanish MICINN/MINECCO
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Linear and branched compounds that contain two, three or five units of galloyl (3,4,5-trihydroxybenzoyl) or its isomer 2,3,4-trihydroxybenzoyl, as well as other mono- or dihydroxybenzoyl moieties have been synthesized. These molecules have been evaluated for their in vitro inhibitory effects against a wide panel of viruses showing preferential activity against HIV and HCV. Our structure-activity relationship studies demonstrated that the 2,3,4-trihydroxybenzoyl moiety provides better antiviral activities than the galloyl (3,4,5-trihydroxybenzoyl) moiety that is present in natural green tea catechins. This observation can be of interest for the further rational exploration of compounds with anti-HCV/HIV properties. The most notable finding with respect to HIV is that the tripodal compounds 43 and 45, with three 2,3,4-trihydroxybenzoyl moieties, showed higher activities than linear compounds with only one or two. With respect to HCV, the linear compounds, 52 and 41, containing a 12 polymethylene chain and two 2,3 di- or 2,3,4 tri-hydroxybenzoyl groups respectively at the ends of the molecule showed good antiviral efficiency. Furthermore, the anti-HCV activity of both compounds was observed at concentrations well below the cytotoxicity threshold. A representative member of these compounds, 41, showed that the anti-HCV activity was largely independent of the genetic make-up of the HCV subgenomic replicon and cell lines used. (C) 2015 Elsevier Masson SAS. All rights reserved.
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