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INTERNATIONAL JOURNAL OF PHARMACEUTICAL RESEARCH

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IJPR included in UGC-Approved List of Journals - Ref. No. is SL. No. 4812 & J. No. 63703

Published by : Advanced Scientific Research
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0975-2366
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IJPR 9[3] July - September 2017 Special Issue

July - September 9[3] 2017

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Synthesis and evaluation of novel α-cyano-N-(2-hydroxyphenyl)cinnamamides for antioxidant, antibacterial and anti-inflammatory activities: In silico prediction of drug likeness properties

Author: MADHAVI KUCHANA,, RENUKA KUMMARI
Abstract: A series of novel substituted α-cyano-N-(2-hydroxyphenyl)cinnamamides were synthesized by Knoevenagel condensation of substituted benzaldehydes with 2-cyano-N-(2-hydroxyphenyl)acetamide. The precursor 2-cyano-N-(2- hydroxyphenyl)acetamide was reported for the first time from our laboratory by cyanoacetylation of 2-aminophenol with 1-cyanoacetyl-3,5-dimethyl pyrazole. The precursor and the title compounds were characterized by their physical and spectral data. All the compounds were evaluated for their antioxidant activity by in vitro models like reduction of 1,1-diphenyl-2-picrylhydrazyl (DPPH) and nitric oxide free radical scavenging. Several compounds found to possess good antioxidant properties and hence the active compounds were evaluated for anti-inflammatory activity by carrageenan induced rat paw edema assay. The animal study revealed that α-cyano-N-(2-hydroxyphenyl)-4-hydroxy-3- methoxycinnamamide was found to possess highest anti-inflammatory activity. All the synthesized compounds were screened for their antibacterial activity by agar well diffusion method using gram negative bacteria Escherichia coli and gram positive bacteria Staphylococcus aureus. Among all the evaluated compounds, α-cyano-N-(2-hydroxyphenyl)-3,4- dihydroxycinnamamide and α-cyano-N-(2-hydroxyphenyl)-3,4,5-trimethoxycinnamamide were found to possess highest zone of inhibition against Escherichia coli and Staphylococcus aureus respectively. Further, in silico prediction of molecular properties and bioactivity scores of all the compounds was performed using molinspiration online property calculation toolkit. All the title compounds found to have drug likeness properties according to Lipinski’s rule of five and predicted as moderately active kinase inhibitors, nuclear receptor ligands and enzyme inhibitors.
Keyword: α-Cyanocinnamamides, 2-Aminophenol, Knoevenagel condensation, Antioxidant activity, Anti-inflammatory activity, Antibacterial activity.
DOI: https://doi.org/10.31838/ijpr/2018.10.03.014
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