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Linear and branched alkyl-esters and amides of gallic acid and other (mono-, di- and tri-) hydroxy benzoyl derivatives as promising anti-HCV inhibitors

AuthorsRivero-Buceta, Eva ; Carrero, P.; Doyagüez, Elisa G.; Madrona, Andrés; Quesada, Ernesto ; Camarasa Rius, María José ; Peréz-Pérez, María-Jesús ; Leyssen, Pieter; Paeshuyse, Jan; Balzarini, Jan; Neyts, Johan; San-Félix, Ana
Antiviral agents
Issue Date2015
CitationEuropean Journal of Medicinal Chemistry 92: 656-671 (2015)
AbstractLinear 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.
Publisher version (URL)http://dx.doi.org/10.1016/j.ejmech.2015.01.033
Identifiersdoi: 10.1016/j.ejmech.2015.01.033
issn: 0223-5234
e-issn: 1768-3254
Appears in Collections:(CENQUIOR) Artículos
(IQM) Artículos
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