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Efficient Synthesis, Antioxidant Activity Evaluation, and Molecular Docking of Novel Isoxazole Derivatives

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Abstract

A series of previously unknown isoxazole-functionalized imidazopyridine derivatives were synthesized in a few steps, starting from pyridine-2,3-diamine. The synthesis involved the reaction of pyridine-2,3-diamine with lactic acid in PEG-400 to prepare 1-(3H-imidazo[4,5-b]pyridin-2-yl)ethanol which was further reacted with propargyl bromide to form 2-[1-(prop-2-yn-1-yloxy)ethyl]-3H-imidazo[4,5-b]pyridine. Finally, the latter was annulated with substituted benzaldehyde oximes in the presence of a catalytic amount of DBU to obtain the target 3-aryl-5-{[1-(3H-imidazo[4,5-b]pyridin-2-yl)ethoxy]methyl}-isoxazoles. The newly synthesized compounds were characterized by IR and NMR spectroscopy and mass spectrometry and showed excellent DPPH/superoxide/nitric oxide activity in antioxidant assay.

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This work was supported by ongoing institutional funding. No additional grants to carry out or direct this particular research were obtained.

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Authors and Affiliations

  1. Department of Chemistry, Kakatiya University, 506009, Warangal, India

    M. Shilpa, B. Krishna, B. Uma & G. Hanmanthu

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  1. M. Shilpa
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  2. B. Krishna
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Correspondence to G. Hanmanthu.

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Shilpa, M., Krishna, B., Uma, B. et al. Efficient Synthesis, Antioxidant Activity Evaluation, and Molecular Docking of Novel Isoxazole Derivatives. Russ J Org Chem 59, 1961–1967 (2023). https://doi.org/10.1134/S1070428023110143

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