Design, synthesis, biological activity, molecular docking and computational studies on novel 1,4-disubstituted-1,2,3-Triazole-Thiosemicarbazone hybrid molecules

A library of some novel 1,4-disubstituted-1,2,3-triazole-thiosemicarbazone hybrid molecules were designed and synthesized from (4-Prop-2-ynyloxy-benzylidene)-thiosemicarbazone and aryl azides under Cu(I)-catalyzed cycloaddition reaction. All newly synthesized [4-(1-Benzyl-1H-[1,2,3]triazol-4-ylmethoxy)-benzylidene] -thiosemicarbazone hybrid molecules were efficiently characterized by IR, H-1 NMR, C-13 NMR, HRMS and structure of alkynes 3 & 12 were finally supported by X-ray crystallographic data. Compounds 5c, 5d, 9c, 9d 13c and 13d demonstrated excellent potency results for B. Subtilis and P. Aeruginosa bacterial strains with MIC values 0.0141, 0.0152, 0.0562, 0.0608, 0.0141, 0.0608, 0.0141, 0.0304, 0.0281, 0.0304, 0.0281, 0.0304, respectively as compared to reference drug Ciprofloxacin. Antibacterial activity results were supported by molecular docking and DFT studies. (C) 2020 Elsevier B.V. All rights reserved.