Synthesis, Biological Evaluation, and Molecular Docking Studies of Some N‐thiazolyl Hydrazones and Indenopyrazolones

Two new series of N-thiazolyl hydrazones (3a-h) and indenopyrazolones (4a-h) were synthesized by the reaction of various 2-acyl-(1H)-indene-1,3(2H)-diones, thiosemicarbazide, and phenacyl bromide/substituted phenacyl bromides. The in vitro antimicrobial activity of these synthesized compounds was assayed against four bacteria, namely, Bacillus subtilis, Staphylococcus aureus, Escherichia coli, and Pseudomonas aeruginosa, and two fungi, namely, Candida albicans and Aspergillus niger, by employing serial dilution method. Ciprofloxacin and fluconazole were used as antibacterial and antifungal reference drugs, respectively. Results of antimicrobial assay showed that the tested compounds have broad range of activity. The compounds 3h and 4a against C. albicans displayed more potency than fluconazole whereas 3b and 3c against B. subtilis showed activity comparable with ciprofloxacin. The synthesized indenopyrazolones (4a-h) were evaluated for their in vitro antioxidant activity by 2,2-diphenyl-1-picrylhydrazyl radical scavenging assay using ascorbic acid as reference. Compound 4b exhibited the highest 2,2-diphenyl-1-picrylhydrazyl radical scavenging with IC50 value 33.14 mu g/mL. The observed results of antimicrobial activity were supported by molecular docking study performed to understand the binding interaction of hydrazones (3a-h) and indenopyrazolones (4a-h) with lanosterol 14 alpha-demethylase.