Synthesis, Antimicrobial, Antioxidant Evaluation, and DFT Estimation of some New Cyclohexenone Derivatives Derived from Benzyloxy Chalcones

Author:

Noori Abdullah Media1ORCID

Affiliation:

1. Department of Chemistry, College of Science, Salahaddin University-Erbil, Kirkuk Road, Kurdistan Region, Iraq

Abstract

Background:: New cyclohexenone derivatives candidates were designed to discover their antioxidant and antibacterial activity potentials, respectively. Methods: Aldehydes with the diverse functional group were prepared from 4-hydroxy benzaldehyde and benzyl bromide and converted to chalcones by reaction with 4-substituted benzophenones and 2-acetyl naphthalene. When chalcone derivatives were subjected to ethyl acetoacetate, it produced new cyclohexenone derivatives through NaOH- catalyzed addition-ring closure reaction. The new compound structures were strengthened by their spectral information. The new compounds are examined for in vitro antifungal and antibacterial actions through broth microdilution technique, and they exhibited potential responses against various bacteria and fungi. Results: As a result, composites with (-F) group as a substituent on para position were established to be the forceful derivatives against S. aureus, E. coli organism, and C. albicans since this compound could inhibit the microbial and Fungai growth at lower concentrations compared to the standards (Ciprofloxacin HCl, and Fluconazole). Conclusion: DPPH radical scavenging experiments were used to evaluate proton donating antioxidant effects; it was exposed that compound 7c has the most significant antioxidant activity, while less than the standard ascorbic acid. Finally, HOMO-LUMO was calculated, which represents the quantum mechanical calculations of energies and conducted by the theory of density functional (DFT) method based on the level of (B3LYP) with 6-31G (d, p) basis set.

Publisher

Bentham Science Publishers Ltd.

Subject

Organic Chemistry,Biochemistry

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