Synthesis, characterization of isoxazole derivatives and evaluation of their antibacterial, antioxidant and anticancer activity

Ketan Vashisht
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Pooja Sethi
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Email src
Anshul Bansal
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Tejveer Singh
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Raman Kumar
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Hardeep Singh Tuli
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Shallu Saini
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Department of Chemistry, M.M. Engineering College, Maharishi Markandeshwar (Deemed to be University), Mullana, Haryana, India
Department of Chemistry, MMEC, Maharishi Markandeshwar (Deemed to be University), Haryana, India
Department of Chemistry, S.A. Jain College, Ambala, Haryana, India
TranslationalOncology Laboratory, Department of Zoology, Hansraj College, University of Delhi, India
Department of Bio-Sciences and Technology, M.M. Engineering College, Maharishi Markandeshwar (Deemed to be University), Mullana, Haryana, India
Department of Bio-Sciences and Technology, MMEC, Maharishi Markandeshwar (Deemed to be University), Haryana, India
Department of Bio-Sciences and Technology, M.M. Engineering College, Maharishi Markandeshwar (Deemed to be University), Mullana, Haryana, India
Received: 7 December 2023 / Revised: 8 February 2024 / Accepted: 13 February .2024 / Published: 30 June 2024

Abstract

Introduction and aim. The synthesis of heterocyclic compounds containing oxygen and nitrogen is profoundly intriguing due to their mechanistic implications in both research and development within organic chemistry and drug discovery. The primary aim of this study is to fabricate a range of pharmacologically active drugs containing the isoxazole moiety.

Material and methods. The synthesis of new derivatives of isoxazole was achieved through a one-pot condensation reaction of 2-[(Substituted phenyl)hydrazono]malononitrile (1) and 3-[(Substituted phenyl)azo]-2,4-Pentanedione (2) with sodium acetate and hydroxylamine hydrochloride (1:1) in ethanol. All the compounds were screened for their in vitro antibacterial activity, in vitro antioxidant and anticancer activity. The synthesized compounds underwent characterization through FTIR, 1 H NMR, and 13C NMR analyses, supported by mass spectral data and elemental analysis.

Results. A set of novel isoxazole derivatives was synthesized with a favorable yield. Among compounds 1d, 1e, 2c, 2d, and 2e exhibited notable antioxidant activities. Compounds 1a, 1b, and 1c demonstrated significant anticancer potential against prostate cancer [PC3] cell lines compared to normal HEK cell lines, while 2a displayed the highest inhibitory zone against Escherichia coli.

Conclusion. Novel compounds with multifaceted biological activities have been successfully designed, and a synthetic route to create isoxazole derivatives has been devised and verified.

 

Cite

Vashisht K, Sethi P, Bansal A, Singh T, Kumar R, Tuli HS, Saini S. Synthesis, characterization of isoxazole derivatives and evaluation of their antibacterial, antioxidant and anticancer activity. Eur J Clin Exp Med. 2024;22(2):376–387. doi: 10.15584/ejcem.2024.2.25.

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