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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
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| Author:
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MADHAVI KUCHANA,, RENUKA KUMMARI
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| Abstract:
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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.
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| Keyword:
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α-Cyanocinnamamides, 2-Aminophenol, Knoevenagel condensation, Antioxidant activity, Anti-inflammatory activity, Antibacterial activity.
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| EOI:
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| DOI:
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https://doi.org/10.31838/ijpr/2018.10.03.014
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| Download:
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