RSC Advances p. 65153 - 65166 (2015)
Update date:2022-08-23
Topics:
Vzquez, Karina
Espinosa-Bustos, Christian
Soto-Delgado, Jorge
Tapia, Ricardo A.
Varela, Javier
Birriel, Estefana
Segura, Rodrigo
Pizarro, Jaime
Cerecetto, Hugo
Gonzlez, Mercedes
Paulino, Margot
Salas, Cristian O.
A set of new aryloxy-quinones were synthesized and evaluated in vitro against the epimastigote form of Trypanosoma cruzi and their unspecific cytotoxicity was tested on murine macrophages J-774 cells. Most of these novel compounds were found to be much more potent and selective than the standard drug nifurtimox. Interestingly, 2-phenoxy-naphthoquinone 3b displayed a remarkable nanomolar inhibitory activity, IC50 = 20 nM, and a high selectivity index, SI = 625. The Epc1 was determined for the most interesting compounds and no correlation with the trypanosomicidal effect was found. Therefore, an in silico study was carried out to obtain a pharmacophoric model and quantitative structure-trypanosomicidal activity relationship. The designed pharmacophore recognized the more potent and selective molecules, exhibiting five pharmacophoric features. A correlation coefficient R2 of 0.99 of pIC50 plotted against the predicted values indicated that the 3D-QSAR equation could be applied to further predictions of newly designed trypanosomicidal compounds.
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