1286670-67-4Relevant academic research and scientific papers
Design, synthesis, and biological activity of novel 5-((arylfuran/1 H -pyrrol-2-yl)methylene)-2-thioxo-3-(3-(trifluoromethyl)phenyl) thiazolidin-4-ones as HIV-1 fusion inhibitors targeting gp41
Jiang, Shibo,Tala, Srinivasa R.,Lu, Hong,Abo-Dya, Nader E.,Avan, Ilker,Gyanda, Kapil,Lu, Lu,Katritzky, Alan R.,Debnath, Asim K.
, p. 572 - 579 (2011/03/20)
On the basis of our earlier molecular docking analysis, we designed and synthesized 5-((arylfuran/1H-pyrrol-2-yl)methylene)-2-thioxo-3-(3- (trifluoromethyl)phenyl)thiazolidin-4-ones (12a-o) as HIV-1 entry inhibitors. Compounds 12a-o effectively inhibited infection by both laboratory-adapted and primary HIV-1 strains and blocked HIV-1 mediated cell-cell fusion and gp41 six-helix bundle formation. Molecular docking analyses on two highly active inhibitors, 12b, containing a carboxylic acid group, and 12m, containing a tetrazole group, indicated that they both fit snugly into the hydrophobic cavity of HIV-1 gp41 from which each has important ionic interactions with lysine 574 (K574). By contrast, molecular docking of 12i, a less active compound containing a pyrrole instead of a furan ring, indicated a completely different orientation from 12b and 12m and missed critical interactions.
