title: Chromanyl-isoxazolidines as Antibacterial agents: Synthesis, Biological Evaluation, Quantitative Structure Activity Relationship, and Molecular Docking Studies.
abstract: Regio- and stereoselective 1,3-dipolar cycloadditions of C-(chrom-4-one-3-yl)-N-phenylnitrones (N) with different mono-substituted, disubstituted, and cyclic dipolarophiles were carried out to obtain substituted N-phenyl-3'-(chrom-4-one-3-yl)-isoxazolidines (1-40). All the synthesized compounds were assayed for their in vitro antibacterial activity and display significant inhibitory potential; in particular, compound 32 exhibited good inhibitory activity against Salmonella typhymurium-1 & Salmonella typhymurium-2 with minimum inhibitory concentration value of 1.56 μg/mL and also showed good potential against methicillin-resistant Staphylococcus aureus with minimum inhibitory concentration 3.12 μg/mL. Quantitative structure activity relationship investigations with stepwise multiple linear regression analysis and docking simulation studies have been performed for validation of the observed antibacterial potential of the investigated compounds for determination of the most important parameters regulating antibacterial activities.
authors: Bio-Organic and Photochemistry Laboratory, Department of Pharmaceutical Sciences, Guru Nanak Dev University, Amritsar, 143 005, Punjab, India.
authors: Gagandeep
authors: G
authors: Singh
authors: University Institute of Pharmaceutical Sciences, Panjab University, Chandigarh, 160014, India.
authors: Anuradha
authors: A
authors: Sharma
authors: Department of Microbiology, Guru Nanak Dev University, Amritsar, 143 005, Punjab, India.
authors: Harpreet
authors: H
authors: Kaur
authors: Bio-Organic and Photochemistry Laboratory, Department of Pharmaceutical Sciences, Guru Nanak Dev University, Amritsar, 143 005, Punjab, India.
authors: Mohan Paul S
authors: MP
authors: Ishar
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D001665:Binding Sites; D020134:Catalytic Domain; D002867:Chromones / Q000737:chemistry*; D004250:DNA Topoisomerases, Type II / Q000737:chemistry / Q000378:metabolism; D006860:Hydrogen Bonding; D055624:Methicillin-Resistant Staphylococcus aureus / Q000187:drug effects; D062105:Molecular Docking Simulation; D010080:Oxazoles / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D021281:Quantitative Structure-Activity Relationship; D012486:Salmonella typhimurium / Q000187:drug effects; D013237:Stereoisomerism
chemical_list: D000900:Anti-Bacterial Agents; D002867:Chromones; D010080:Oxazoles; D004250:DNA Topoisomerases, Type II
keywords: 1,3-dipolar cycloaddition; 3-chromanyl-isoxazolidines; ADME properties; antibacterial activity; quantitative structure activity relationship