Indolyl‐4H‐Chromene Derivatives as Antibacterial Agents: Synthesis, in Vitro and in Silico Studies

Author:

Anaikutti Parthiban1,Adhikari Priyanka1,Baskaran Sambath2,Selvaraj Mangalaraj3,Afzal Mohd4ORCID,Makam Parameshwar5ORCID

Affiliation:

1. Centre for GMP Extraction Facility National Institute of Pharmaceutical Education and Research (NIPER-G) Guwahati 781101 Assam India

2. Department of Chemistry University of Ulsan Ulsan 44776, Republic of Korea

3. Department of Chemistry St. Joseph's College (Autonomous) Tiruchirappalli 620002 India

4. Department of Chemistry College of Science King Saud University Riyadh 11451 Saudi Arabia

5. Department of Chemistry School of Applied and Life Sciences Uttaranchal University, Arcadia Grant, P.O. Chandanwari, Premnagar Dehradun Uttarakhand 248007 India

Abstract

AbstractIn this study, indolyl‐4H‐chromene derivatives are designed and synthesised using an eco‐friendly multicomponent one‐pot synthesis using benzaldehydes, nitroketene N, S‐acetals, and indoles combine with InCl3, a Lewis acid catalyst, and ethanol, an environmentally acceptable solvent. Due to antibiotic resistance, assessed these Indolyl‐4H‐chromene derivatives for their in vitro antibacterial activity against Gram‐positive and Gram‐negative bacteria, including Streptococcus pyogenes, Staphylococcus aureus, Clostridium pyrogenes, Bacillus subtilis, Escherichia coli, and Pseudomonas aeruginosa, using the agar well diffusion method and Minimum Inhibition Concentration (MIC) assay. Three compounds, 4‐(1H‐indol‐3‐yl)‐6‐methoxy‐N‐methyl‐3‐nitro‐4H‐chromen‐2‐amine, 4‐(1H‐indol‐3‐yl)‐3‐nitro‐N‐phenyl‐4H‐chromen‐2‐amine and 4‐(6‐Fluoro‐1H‐Indol‐3‐yl)‐N‐methyl‐3‐nitro‐4H‐chromen‐2‐amine showed better zone of inhibition (mm) and Minimum Inhibition Concentration (MIC) values of 10 μg/mL to 25 μg/mL against all bacterial types. The Ki values of 278.60 nM and 2.21 nM for compound 4‐(1H‐indol‐3‐yl)‐3‐nitro‐N‐phenyl‐4H‐chromen‐2‐amine showed improved interactions with DNA gyrase B and topoIV ParE′s ATP binding sites in in silico studies.

Publisher

Wiley

Subject

Molecular Biology,Molecular Medicine,General Chemistry,Biochemistry,General Medicine,Bioengineering

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