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Volume 30
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This is an early access version, the complete PDF, HTML, and XML versions will be available soon.
Article

Studies of the Synthesis of Fused Isoxazoline/Isoquinolinones and Evaluation of the Antifungal Activity of Isoxazole-like Benzamide and Isoquinolinone Hybrids

by
Konstantinos A. Ouzounthanasis
1,
Jasmina Glamočlija
2,
Ana Ćirić
2 and
Alexandros E. Koumbis
1,*
1
Laboratory of Organic Chemistry, Department of Chemistry, Aristotle University of Thessaloniki, 54124 Thessaloniki, Greece
2
Department of Plant Physiology, Institute for Biological Research “Siniša Stanković”—National Institute of Republic of Serbia, University of Belgrade, 11060 Belgrade, Serbia
*
Author to whom correspondence should be addressed.
Molecules 2025, 30(3), 589; https://doi.org/10.3390/molecules30030589
Submission received: 28 December 2024 / Revised: 26 January 2025 / Accepted: 26 January 2025 / Published: 27 January 2025
(This article belongs to the Section Organic Chemistry)
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Abstract

Isoxazole derivatives (isoxazoles, isoxazolines, and isoxazolidines) are present in the structure of several natural products and/or pharmaceutically interesting compounds. In this work, a synthetic study for the preparation of fused isoxazoline/isoquinolinone hybrids is presented. The initial approach involving the sequential 1,3-dipolar cycloaddition of nitrile oxides to indenone (to obtain the isoxazoline ring) and a Beckmann rearrangement (to construct the isoquinolinone lactam system) was complicated by the formation of fragmentation products during the latter. Therefore, the desired hybrids were successfully reached by applying DDQ-mediated oxidation of the respective isoxazolidines. Based on the results, key observations were made regarding the mechanism of the Beckmann reaction. Moreover, selected isoxazole benzamides and fused isoxazoline/isoxazolidine isoquinolinones were in vitro evaluated against a series of fungi strains (including a 2D checkerboard assay with ketoconazole), revealing that some of these compounds exhibit promising antifungal activity.
Keywords: isoxazole; isoxazoline; isoxazolidine; isoquinolinone; benzamide; 1,3-dipolar cycloaddition; nitrile oxide; Beckmann rearrangement; oxidation; antifungal activity isoxazole; isoxazoline; isoxazolidine; isoquinolinone; benzamide; 1,3-dipolar cycloaddition; nitrile oxide; Beckmann rearrangement; oxidation; antifungal activity
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MDPI and ACS Style

Ouzounthanasis, K.A.; Glamočlija, J.; Ćirić, A.; Koumbis, A.E. Studies of the Synthesis of Fused Isoxazoline/Isoquinolinones and Evaluation of the Antifungal Activity of Isoxazole-like Benzamide and Isoquinolinone Hybrids. Molecules 2025, 30, 589. https://doi.org/10.3390/molecules30030589

AMA Style

Ouzounthanasis KA, Glamočlija J, Ćirić A, Koumbis AE. Studies of the Synthesis of Fused Isoxazoline/Isoquinolinones and Evaluation of the Antifungal Activity of Isoxazole-like Benzamide and Isoquinolinone Hybrids. Molecules. 2025; 30(3):589. https://doi.org/10.3390/molecules30030589

Chicago/Turabian Style

Ouzounthanasis, Konstantinos A., Jasmina Glamočlija, Ana Ćirić, and Alexandros E. Koumbis. 2025. "Studies of the Synthesis of Fused Isoxazoline/Isoquinolinones and Evaluation of the Antifungal Activity of Isoxazole-like Benzamide and Isoquinolinone Hybrids" Molecules 30, no. 3: 589. https://doi.org/10.3390/molecules30030589

APA Style

Ouzounthanasis, K. A., Glamočlija, J., Ćirić, A., & Koumbis, A. E. (2025). Studies of the Synthesis of Fused Isoxazoline/Isoquinolinones and Evaluation of the Antifungal Activity of Isoxazole-like Benzamide and Isoquinolinone Hybrids. Molecules, 30(3), 589. https://doi.org/10.3390/molecules30030589

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