Synthesis, molecular docking and DFT studies on biologically active 1,4-disubstituted-1,2,3-triazole-semicarbazone hybrid molecules

Abstract

Some biologically active semicarbazone-triazole hybrid molecules have been designed and synthesized from semicarbazone linked terminal alkyne and aromatic azides via Cu(I)-catalyzed cycloaddition reactions. All newly synthesized compounds were successfully characterized by using IR, ¹H-NMR, ¹³C-NMR, and HRMS spectral techniques. The synthesized molecules were screened in vitro for anti-bactericidal effects on E. coli (MTCC 16521), B. subtilis (MTCC441), S. aureus (MTCC 3160), P. aeruginosa (MTCC 424) and S. epidermidis (MTCC 6880). The antibacterial property results revealed that the semicarbazone-triazole hybrid molecules (9b, 9e, and 9f) are a better alternative to the existing antibacterial drug ciprofloxacin. The docking study on the most active compound 9b and its alkyne precursor 8 with the DNA gyrase enzyme of E. coli bacteria supported the biological activity results.