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Synthesis, Antioxidant, and Antibacterial Activities of Two Novel Series of 3,5-Disubstituted Isoxazole Ether-Linked Isoxazolines and 3,5-Disubstituted Pyrazole Ether-Linked Isoxazolines Mediated by Chloramine-T

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Abstract

Two short novel series of five membered heterocyclic 3,5-disubstituted–Isoxazole ether-linked Isoxazoline derivatives (Xa–f) and 3,5-disubstituted-Pyrazole ether-linked Isoxazoline derivatives (XIa–f) were synthesized via 1,3-dipolar cycloaddition reaction of Isoxazole ether-linked allyloxymethyl (VI) and pyrazole ether-linked allyloxymethyl (VII) with aromatic aldoximes (VIIIa–f) which undergo oxidative dehydrogenation with chloramine-T (IX) to give 3,5-disubstituted isoxazole ether-linked isoxazoline derivatives (Xa–f) and 3,5-disubstituted pyrazole ether-linked Isoxazoline derivatives (XIa–f) in good yield. The newly synthesized compounds were screened for anti-oxidant and anti-microbial activities. 3,5‑Disubstituted isoxazole ether-linked isoxazoline derivatives (Xc–d) and 3,5-disubstituted Pyrazole ether-linked isoxazoline derivatives (XIc–d) exhibited antioxidant activity at 10 µg/mL, as well as anti-microbial activity at 100 µg/mL compared with standard vitamin C and ciprofloxacin, respectively. Structures of newly synthesized compounds were established on the basis of their elemental analysis and spectral IR, 1H NMR, and 13C NMR.

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ACKNOWLEDGMENTS

Author expresses his sincere gratitude to the University of Mysore, Mysore, for providing the laboratory facilities to carry out this work.

Funding

This work was funded by the Deanship of Scientific Research at Prince Sattam Bin Abdulaziz University through Award Number 2021/01/18335.

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Authors and Affiliations

  1. Department of Chemistry, Prince Sattam Bin Abdulaziz University, College of Arts and Science, 11991, Wadi Al-Dawasir, Saudi Arabia

    E. A. M. Saleh, I. Hassan & K. Husain

  2. Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore, 570006, India

    S. Y. Kotian & K. M. L. Rai

  3. Department of Chemistry, Prince Sattam Bin Abdulaziz University, College of Arts and Science, AL Kharj, Saudi Arabia

    A. M. Al Dawsari

  4. Center for Materials Science & Technology, University of Mysore, Vijnan Bhavan, Manasagangotri, Mysore, 570006, India

    P. C. Abishad & K. Byrappa

  5. Department of Mathematics, Prince Sattam Bin Abdulaziz University, College of Arts and Science, 11991, Wadi Al-Dawasir, Saudi Arabia

    R. S. S. AL Sharabi

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  1. E. A. M. Saleh
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Saleh, E.A., Kotian, S.Y., Al Dawsari, A.M. et al. Synthesis, Antioxidant, and Antibacterial Activities of Two Novel Series of 3,5-Disubstituted Isoxazole Ether-Linked Isoxazolines and 3,5-Disubstituted Pyrazole Ether-Linked Isoxazolines Mediated by Chloramine-T. Russ J Bioorg Chem 48, 1043–1052 (2022). https://doi.org/10.1134/S1068162022050181

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