Cu(II)-Catalyzed Green Synthesis of 1,4,5-Trisubstituted-1,2,3-Triazoles from Chalcone Derivatives - Studies on Their Cytotoxicity Profile

Triazoles are an important class of heterocyclic compounds due to their interesting structural features and versatile biological significance. In this regard, the present work highlights the synthesis of Cu(II)-catalyzed 1,2,3-trisubstituted triazoles through the cycloaddition of different chalcones with azides under neat methodology. A series of 16 triazole derivatives (3 a to 3 o) was prepared using 10 mol % Cu(II) complexes of 1,10-phenanthroline and terpyridine-based ligands as catalysts with moderate to excellent yields. All these derivatives were structurally analyzed by UV-visible, infrared, 1H, 13C NMR and mass spectral data. The product, (4-((4-benzoyl-5-(4-fluorophenyl)-1H-1,2,3-triazol-1-yl) methyl)benzonitrile) (3 j) was structurally analyzed by single crystal XRD analysis. Also, the molecular structure of one of the catalysts, [Cu(Phen)2]2+(NO3-)2) was obtained by single crystal XRD analysis. Additional investigations of all these derivatives exhibited potential cytotoxic characteristics against MCF-7 cancer cell lines. Among them, compounds 3 j, 3 i, 3 c, 3 d and 3 g facilitated the notable IC50 values. Moreover, the studies on the photophysical properties of synthesized derivatives showed the absorption bands in the range of 267-290 nm, depending on the nature of the substituent and the compounds 3 e and 3 f demonstrated the highest and lowest quantum yields as 0.05339 % and 0.01914 %, respectively. The present work describes the new synthesis of Cu(II)-catalyzed 1,2,3-trisubstituted triazole derivatives through the cycloaddition of different chalcones with azides under neat conditions. The triazole derivatives exhibit potential cytotoxic characteristics against MCF-7 cancer cell lines with notable IC50 values. The photophysical properties of the products strongly depend on the nature of the substituents. image