Click-chemistry-inspired synthesis of new series of 1,2,3-triazole fused chromene with glucose triazole conjugates: Antibacterial activity assessment with molecular docking evaluation.

Autor: Ahemad MA; Organic Synthesis Laboratory, Department of Chemistry, Ravenshaw University, Cuttack, 753003, Odisha, India., Patra A; Organic Synthesis Laboratory, Department of Chemistry, Ravenshaw University, Cuttack, 753003, Odisha, India., Muduli L; Organic Synthesis Laboratory, Department of Chemistry, Ravenshaw University, Cuttack, 753003, Odisha, India., Nayak S; Organic Synthesis Laboratory, Department of Chemistry, Ravenshaw University, Cuttack, 753003, Odisha, India. Electronic address: sabitanayak@ravenshawuniversity.ac.in., Mohapatra S; Organic Synthesis Laboratory, Department of Chemistry, Ravenshaw University, Cuttack, 753003, Odisha, India., Panda J; Organic Synthesis Laboratory, Department of Chemistry, Ravenshaw University, Cuttack, 753003, Odisha, India., Sahoo CR; ICMR-Regional Medical Research Centre, Department of Health Research, Ministry of Health & Family Welfare, Govt. of India, Bhubaneswar, 751023, Odisha, India.
Jazyk: angličtina
Zdroj: Carbohydrate research [Carbohydr Res] 2024 Sep; Vol. 543, pp. 109222. Date of Electronic Publication: 2024 Jul 30.
DOI: 10.1016/j.carres.2024.109222
Abstrakt: A series of new 1,2,3-triazole fused chromene based glucose triazole conjugates were synthesized from chromene fused 1,2,3-triazolyl extended alkyne and 2,3,4,6-tetra-O-acetyl-β-d-glucopyranosyl azide in good to excellent yield by a copper catalyzed azide-alkyne cycloaddition (CuAAC) reaction. The major advantages include mild reaction conditions, high yield, good substrate scope, and shorter reaction time. The antibacterial efficacy of the compounds were assessed in vitro against human pathogenic Gram-negative E. coli and Gram-positive S. aureus bacteria. Compound 24j was found to be the most potent molecule with zone of inhibition (ZI) of 17 mm and minimum inhibitory concentration (MIC) of 25 μg mL -1 in E. coli and ZI of 16 mm and MIC of 25 μg mL -1 in S. aureus. Also, it significantly inhibited E. coli DNA-gyrase in silico with a binding affinity of -9.4 kcal/mol. Among all the synthesized compounds, 24i, 24d, 24e and 24f showed significant antibacterial activity against both strains and inhibited DNA-gyrase in silico with good binding affinities. Hence, these 1,2,3-triazole fused chromene based glucose triazole conjugates may evolve to be powerful antibacterial agents in recent future, according to structure-activity relationships based on strong antibacterial properties and molecular docking studies.
Competing Interests: Declaration of competing interest We declare that we have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.
(Copyright © 2024 Elsevier Ltd. All rights reserved.)
Databáze: MEDLINE
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