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Current Organic Synthesis

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ISSN (Print): 1570-1794
ISSN (Online): 1875-6271

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Research Article

Synthesis, Anti-Bacterial and Anti-Oxidant Activity of Azo-Oxazolone and Their Ring Opening Azo-Benzamide Derivatives

Author(s): Mzgin M. Ayoob*, Awaz J. Hussein, Mohammed K. Samad, Necmi Dege, Farouq E. Hawaiz, Shaaban K. Mohamed and Faiq H.S. Hussain

Volume 18, Issue 5, 2021

Published on: 18 December, 2020

Page: [493 - 505] Pages: 13

DOI: 10.2174/1570179417666201218163435

Price: $65

Abstract

This article describes the controlled synthesis and characterization of azo oxazolone scaffold compounds containing multifunctional groups such as carbonyl group, imine and carbon-carbon double bond. The reaction of the azo-oxazolone with aromatic amines led to the ring-opening of the azo-oxazolone into the corresponding azo-benzamide derivatives in a short time (average 10 min), resulting in high yield (>90%). All newly synthesized compounds were characterized by the common spectral analysis such as UV, IR, 1H-NMR, 13CNMR, Elemental analysis and MS spectrometry.

Objective: The aim of the study was to synthesize new bioactive azo-benzamides by using azo-oxazolone as a synthon utilizing its ring-opening function.

Materials and Methods: Azo-benzamide derivatives were prepared in very good yield via ring-opening reaction of azo-oxazolone with aromatic amines in the presence of acetic acid under reflux for few minutes.

Results and Discussion: Chemical structures of the newly synthesized compounds were characterized by UV, IR, 1H-NMR, 13C-NMR, Elemental analysis and MS spectrometry.

Conclusion: The new azo-oxazolone 4 and azo-benzamide compounds 5a, 5c, 5f, 5h, 5j were screened against Escherichia coli as G(-ve) and Staphylococcus aureus as G(+ve) using ciprofloxacin as a standard. All compounds showed high inhibition potency against E-Coli but low inhibition for S-aureus. Compounds 4, 5c, and 5J showed more reactivity against E-coli.

Others: Also, the compounds were tested for their anti-oxidant activity by both DPPH and FRAP methods. The results showed that some compounds possessed moderate anti-oxidant activity in comparison to ascorbic acid as control, typically the compounds bearing OCH3 and OCH2CH3 groups.

Keywords: Azo-oxazolone, azo-benzamide, antimicrobial, antioxidant, ring-opening reaction, MS spectrometry.

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