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Synthesis, Molecular Docking and Biological Evaluation of 2‐Aryloxy‐<i>N</i>‐Phenylacetamide and <i>N′</i>‐(2‐Aryloxyoxyacetyl) Benzohydrazide Derivatives as Potential Antibacterial Agents

Vidyasrilekha Yele, Mohammad Afzal Azam, Ashish Wadhwani

2021Chemistry & Biodiversity33 citationsDOI

Abstract

Abstract A new class of 2‐aryloxy‐ N ‐phenylacetamide and N′ ‐(2‐aryloxyoxyacetyl) benzohydrazide derivatives with different active moieties were synthesized and screened for their antibacterial activity. Structural characterization of synthesized compounds was performed using HR‐MS, 1 H‐NMR, and 13 C‐NMR spectral data. Amongst the synthesized compounds, 4‐{2‐[2‐(2‐chloroacetamido)phenoxy]acetamido}‐3‐nitrobenzoic acid ( 3h ) and 2‐chloro‐ N ‐(2‐{2‐[2‐(2‐chlorobenzoyl)hydrazinyl]‐2‐oxoethoxy}phenyl)acetamide ( 3o ) have shown good antibacterial activity against a selected panel of bacteria. Besides, compounds also exhibited bactericidal activity against P. aeruginosa ( 3h , 0.69 μg/mL) and S. aureus ( 3o , 0.62 μg/mL) as evident by MBC and time‐kill kinetics studies. In silico molecular docking and ADMET properties of newly synthesized compounds revealed that compounds could be considered as promising antibacterial agents.

Topics & Concepts

AcetamideChemistryAntibacterial activityDocking (animal)StereochemistryCombinatorial chemistryIn silicoBacteriaOrganic chemistryBiochemistryMedicineNursingBiologyGeneGeneticsSynthesis and biological activityPhenothiazines and Benzothiazines Synthesis and ActivitiesSynthesis and Biological Evaluation