Abstract
In this paper, N-functionalized derivatives of methyl anthranilate (1–3) were prepared by reacting it with various acid chlorides to give amide derivatives (1–3) which were further converted to benzohydrazide derivatives (4–6) by reacting them with hydrazine. These N-functionalized derivatives of 2-aminobenzohydrazide (4–6) were reacted with 4-triflouromethyl benzaldehyde to give schiff base derivatives (7–9). All the synthesized compounds (1–9) were characterized by Mass spectrometry as well as NMR and FTIR spectroscopic techniques. Single Crystal X-ray diffraction analysis technique (XRD) was utilized to analyze crystalline compound 1. AChE and BChE enzymes inhibition potential was checked for the synthesized compounds. Putative binding approaches of screened compounds were explored by molecular docking studies. Synthesized compounds were also checked for antioxidant activity. Enzyme inhibition analysis showed that compounds 2 and 9 exhibited good AChE inhibition showing 68% and 60% percentage inhibition, respectively, while very good BChE inhibition activities were shown by compounds 2 (70%) and 5 (76%). Enzyme inhibition results were also supported by molecular docking studies with lowest binding energy values of −9.79 kcal mol−1 for BChE and −9.55 kcal mol−1 for AChE for compound 9. Hydrazide derivatives (4–6) showed very significant results for antioxidant activity with percentage scavenging greater than 90%.
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•N-functionalized derivatives of 2-aminobenzohydrazide were synthesized.•The benzohydrazides bearing hydrogen donating groups showed good Antioxidant activities.•Good enzyme inhibition activity against AChE and BChE were shown by amide derivatives of benzohydrazides.•Molecular docking evaluation also supported the experimental results for enzyme inhibition.