Chalcone-based dipolar cycloaddition of novel heteroaromatic compounds: Their anticancer examination

Abstract

In this study, new chalcone-isoxazole-based hybrid derivatives (12, 13, 18, and 21) and chalcone-triazole hybrid molecules (26) were synthesized using the click chemistry approach. Among these hybrid molecules, 12, 13, 21, and 26 were obtained by combining azole pharmacophore groups such as thiazole, isoxazole, and 1,2,3-triazole. In addition, a new bioactive hybrid molecule (E)-3-(2-(1-((4- (3-(4-((3-(4-(benzyloxy) phenyl) isoxazol-5-yl) methoxy) phenyl)–3–oxoprop-1-en-1-yl) phenoxy)methyl)-1H-1,2,3-triazol-4-yl)thiazol-4-yl)-2H-chromen-2-one (18), which is a chalcone-isoxazole hybrid derivative with azido thiazole coumarin substitution, was synthesized. The chemical structures of synthesized compounds were characterized by spectroscopic techniques such as 1H NMR, 13C NMR, FT-IR, and MALDI-TOF MS (18, 21, and 26). These novel chalcone-azole hybrids (12, 13, 18, 21, and 26) were investigated for their in-vitro anticancer activity against A549 cells, Capan-1 cell lines, and a healthy L929 fibroblast cell line, as well as the apoptotic and necrotic effects of these compounds on Capan-1 cell lines. Among the compounds tested, hybrid 18 showed the best activity in the A549 cell line, while it showed moderate activity in the Capan-1 cell line.