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

Abstract

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 μg/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 14α‐demethylase.

Recent Developments in the Synthesis of N‐Heterocyclic Compounds as α‐Amylase Inhibitors via In‐Vitro and In‐Silico Analysis: Future Drugs for Treating Diabetes

“…Derivative possessing isopropyl and chlorine substituent at R 1 and R 2 respectively have shown better inhibition potential against αamylase. [41][42][43][44][45] Figure 5 shows that thiozolidine-pyrazole derivatives with nitro group (20 L) has shown best activity among all the compounds of pyrazole, pyrazolone and pyrazoline series. This is due to presence of thiazolidine ring.…”

“…Amylase inhibitory analysis displayed good inhibitory activity with IC 50 =11.90–68.36 μM as compared to standard acarbose with IC 50 =22.87 μM. Derivative possessing isopropyl and chlorine substituent at R 1 and R 2 respectively have shown better inhibition potential against α‐ amylase [41–45] …”

Synthesis, Biological Evaluation, Migratory Inhibition and Docking Study of Indenopyrazolones as Potential Anticancer Agents

“…We have systematically synthesized eight biologically active indenopyrazolones through an efficient one‐pot method, as shown in Scheme 1. Researchers effectively employed different methods for the synthesis of pyrazolones in the absence [40] or presence of catalysts such as acetic acid, [41] [HMIM]HSO 4 [42] 3‐aminopropylated silica gel, [43] sodium dodecyl sulfate, [44] silica‐bonded S ‐sulfonic acid [45] and Ce/SiO 2 composite [46] according to the related literature.…”

Synthesis, Type II diabetes inhibitory activity, antimicrobial evaluation, and docking studies of N'-arylidene-2-((7-methylbenzo[4,5]thiazolo[2,3-c] [1,2,4]triazol-3-yl)thio)acetohydrazides

“…Taking into account the above facts, and in continuation of our program directed for the development of new, simple, safer, and efficient procedures for the synthesis of biologically active heterocyclic compounds utilizing readily accessible starting substrates and intermediates [30][31][32][33][34][35], here we report synthesis, characterization, Type II diabetes inhibitory activity and antimicrobial evaluation and docking studies of N'-arylidene-2-((7-methylbenzo [4,5]thiazolo[2, 3-c][1, 2, 4]triazol-3-yl)thio) acetohydrazides (6a-j) and their precursors 1-4.…”