Synthesis, cytotoxic evaluation, molecular docking studies and drug-likeness analysis of some novel 2-[(9-ethyl-9 <i>H</i> -carbazol-3-yl)imino]thiazoles/thiazolidinones

Abstract

A novel series of some 2-[(9-ethyl-9H-carbazol-3-yl)imino]thiazoles/thiazolidinones was synthesized and established by spectroscopic tools and elemental analysis. The synthetic strategy depended on cyclization of 1-(9-ethyl-9H-carbazol-3-yl)-3-phenylthiourea (2) with different α-halocarbonyl compounds and some carbon electrophiles under mild reaction conditions. All products were screened for their in vitro cytotoxic activities toward three human cancer cell lines (MCF-7, HepG-2 and HCT-116). Interestingly, the particular carbazolyl derivatives 7, 13, 14 and 16 exhibited promising cytotoxicity results against all the evaluated cell lines. Also, molecular docking studies for the highly bioactive compounds were achieved to investigate the binding mode toward (VEGFR-2-KDR) receptor. Moreover, anticancer results were validated computationally by applying SwissADME server.