Melanny Ika Sulistyowaty, - and Galih Satrio Putra, - and Wang Zhichao, - and Tutuk Budiati, - (2020) N-(2-(2-Benzilidenehydrazinecarbonyl)phenyl)benzamides: Synthesis, Cytotoxic, Antioxidant Activity and Molecular Docking Studies. Journal of Hunan University Natural Sciences, 47 (10). pp. 199-207. ISSN 1674-2974

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Abstract

This study’s purpose was to continue our research by acquiring novel anticancer candidates, the derivatives of N-(2-(2-benzylidenehydrazinecarbonyl)phenyl)benzamide. The benzamides were synthesized from the starting material, anthranilic acid. The products were examined for their antioxidant activity and bioactivity against human lung cancer in cell line A549. This study also reported the molecular interaction with tyrosine kinase (PDB ID: 1M17) by in silico method. The synthesis was conducted in three reaction steps, consisting of nucleophilic substitution, dehydration reaction, and nucleophilic addition. In vitro anticancer activity of the compounds was examined in the A549 cell line by using the MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl-tetrazolium bromide) method. Free radical scavenger activity of these compounds was also evaluated by DPPH (2,2,1-diphenyl-1-picrylhydrazyl) assay. The virtual molecular docking study was performed using Molegro® version 5.5. The derivatives of N-(2-(2-benzylidenehydrazinecarbonyl)phenyl)benzamide were synthesized in good yields. Among the synthesized compounds, N-(2-(2-(2-hydroxybenzylidene)hydrazinecarbonyl)phenyl)benzamide (3c) had the highest activity in terms of inhibiting the growth of the A549 cell line, with IC50 of 10.88 ± 0.82 μg/mL, which was linear with the docking result. Meanwhile, N-(2-(2-(4-hydroxy-3-methoxybenzylidene)hydrazinecarbonyl)phenyl)benzamide (3f) possessed the highest antioxidant activity, with IC50 of 37.23 ± 3.76 μg/mL.

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