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Green synthesis, antibacterial evaluation and QSAR analysis of some isatin Schiff bases

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Abstract Twelve isatin Schiff bases (1a-7a, 1b-5b) were prepared by reacting isatin and 5-bromoisatin with different anilines using green chemistry (microwave (MW) and ultrasound (US) assisted synthesis). The antibacterial activity… Click to show full abstract

Abstract Twelve isatin Schiff bases (1a-7a, 1b-5b) were prepared by reacting isatin and 5-bromoisatin with different anilines using green chemistry (microwave (MW) and ultrasound (US) assisted synthesis). The antibacterial activity of each compound was evaluated against nine standard and clinical bacterial strains using the Agar-well diffusion method. The lowest-obtained Minimum Inhibitory Concentration (MIC) was 78 μg/mL against Pseudomonas aeruginosa for 1a and 1b. All the synthesized compounds were identified using IR, 1H NMR, 13C NMR and microanalysis. Quantitative Structure Activity Relationship (QSAR) and Molecular Electrostatic Potential Surface (MEPS) analyses were carried out to rationalize antibacterial activity of the synthesized compounds. Based on the QSAR analysis, including DFT-based, steric and hydrophobic descriptors, it was found that molecules with more hydrophobic character associated with less dipole moment act as antibacterial agents against Klebsiella pneumoniae ATCC700603.

Keywords: schiff bases; isatin; synthesis antibacterial; qsar analysis; isatin schiff

Journal Title: Journal of Molecular Structure
Year Published: 2020

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