Coumarin-triazole hybrids: Design, microwave-assisted synthesis, crystal and molecular structure, theoretical and computational studies and screening for their anticancer potentials against PC-3 and DU-145

This study presents the synthesis of series of alpha,beta-unsaturated carbonyl linked coumarin-triazole hybrids, 7(a-e) by microwave irradiation conditions. The target compounds were synthesized in four steps starting from 4-hydroxycoumarin, 1 and substituted aromatic primary amines, 3. Spectroscopic analysis provide the structure proofs of synthesized new compounds 6e and 7(a-e), and the molecular structure of one of the intermediate compound 6e was confirmed by single crystal X-ray diffraction studies. The crystal structure analysis shows that the C-H center dot center dot center dot pi, C-O center dot center dot center dot pi and pi-pi intermolecular interactions stabilizes the crystal structure, the intermolecular interactions are quantified through Hirshfeld surface analysis. To substantiate the X-ray crystal structure, the density functional theory calculations were performed. Further, the target compounds coumarin-triazole hybrids, were screened in vitro for their anticancer activity against PC-3 and DU-145 cell lines. The result shows that, amongst the series, compound 7c was more potent against PC-3 and DU-145 cell lines. (C) 2021 Elsevier B.V. All rights reserved.