Synthesis, characterization, antimicrobial, antioxidant, and antiinflammatory evaluation and molecular docking studies of N-((2-hydroxy-3-(2-(substitutedbenzylidene)hydrazine-1-carbonyl)naphthalen-1-yl)(3-nitrophenyl/3,4-dimethoxyphenyl)methyl)acetamide derivatives

N-((2-羟基-3-(2-(取代亚苄基)肼-1-羰基)萘-1-基)(3-硝基苯基/3,4-二甲氧基苯基)甲基)乙酰胺衍生物的合成、表征、抗菌、抗氧化和抗炎评价及分子对接研究

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Abstract

Hydrazone chemistry has become important and plays a key role in the development of organic compounds. Hydrazones can be useful pharmacophores for creating novel derivatives, owing to their broad range of activities. In this study, a series of N-((2-hydroxy-3-(2-(substitutedbenzylidene)hydrazine-1-carbonyl)naphthalen-1-yl)(3-nitro-phenyl/3,4-dimethoxyphenyl)methyl)acetamide derivatives were prepared, characterized by FTIR, (1)H-NMR, (13)C-NMR, and mass spectroscopy, and evaluated for their antimicrobial, antiinflammatory, and antioxidant activities along with in silico studies. The substituted derivatives were synthesized by the reaction of acetonitrile, chlorosulphonic acid, and substituted benzaldehyde with the hydrazones. The antimicrobial evaluation showed that compound 3i had more antimicrobial potential than the other tested molecules. Compound 3j had more antioxidant potential than the other synthesized compounds. Two compounds, 3f and 3h, had better antiinflammatory activity. The binding affinities of synthesized derivatives into the active sites of receptor proteins were characterized by utilizing the advanced docking program AutoDock Vina. In silico ADMET studies were performed using Molinspiration, pre-ADMET, and OSIRIS property explorer for the prediction of pharmacokinetic behavior of synthesized compounds.

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