Na2S2O3 Catalyzed Three‐Component Synthesis and Anti‐Bacterial Activity of 3‐Methyl‐4‐(hetero)arylmethylene isoxazole‐5(4H)‐ones

Bi, Yongchang; Wang, Jingjun; Bian, Xingyu; Chen, Mingyue; Zhu, Guangyuan; Zhang, Yumin; Gu, Qiang

doi:10.1002/cbdv.202400073

Chemistry & Biodiversity

2024

DOI: 10.1002/cbdv.202400073

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Na₂S₂O₃ Catalyzed Three‐Component Synthesis and Anti‐Bacterial Activity of 3‐Methyl‐4‐(hetero)arylmethylene isoxazole‐5(4H)‐ones

Yongchang Bi,

Jingjun Wang,

Xingyu Bian

et al.

Abstract: An efficient and green method for synthesizing 3‐methyl‐4‐(hetero)arylmethylene isoxazole‐5(4H)‐ones was developed using a recyclable and environmental‐friendly catalyst, Na2S2O3, and 16 target compounds were successfully synthesized under the obtained optimal reaction condition. Using rifampicin as a positive control, the antibacterial activity of all synthesized compounds was tested by micro dilution method, among them, 3‐methyl‐4‐ [(2,4‐dimethoxyphenyl) methylene] ‐ isoxazole‐5‐one (4m) presented wonderful … Show more

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Antimicrobial activity of isoxazole derivatives: A brief overview

Vashisht,

Sethi,

Bansal

et al. 2024

Vietnam Journal of Chemistry

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Due to their extensive range of biological actions, isoxazole and its analogues stand out among other heterocyclic compounds as a very important class of heterocycles. Over recent years, there has been a growing demand for these heterocyclic nuclei as crucial synthetic intermediates, contributing significantly to the advancement of newly formed chemical entities in the fields of pharmaceutical and medicinal chemistry. Furthermore, the significance of N and O‐containing heterocycles from medicinal perspective arises from their inherent ability to readily bind with biological systems, including various enzymes and receptors, through many non‐covalent interactions. The antimicrobial potential of isoxazole compounds has been extensively studied against broad range of microorganisms, including bacteria, fungi, etc. From a research perspective, isoxazoles exhibit antimicrobial, anticancer, antioxidant, analgesic, anti‐inflammatory, and central nervous system activities. It also exhibits inhibitory, glutamate transporter, and anti‐hypertensive properties, which are similar to GABA (γ‐aminobutyric acid). The current review explores the antimicrobial properties and structure‐activity relationship of different isoxazole derivatives relative to their antimicrobial efficacy. Furthermore, it seeks to highlight the potential applications and future directions in the development of isoxazole‐based antimicrobial agents.

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Antimicrobial activity of isoxazole derivatives: A brief overview

Vashisht,

Sethi,

Bansal

et al. 2024

Vietnam Journal of Chemistry

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Synthesis of Isoxazol-5-One Derivatives Catalyzed by Amine-Functionalized Cellulose

Gharehassanlou,

Kiyani

2024

Organics

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In this contribution, propylamine-functionalized cellulose (Cell-Pr-NH2) was employed as the catalyst in the three-component reaction between hydroxylamine hydrochloride and various types of aryl/heteroaryl aldehydes, ethyl acetoacetate/ethyl 4-chloroacetoacetate, or ethyl 3-oxohexanoate. The result of these experiments was the formation of 3,4-disubstituted isoxazol-5(4H)-one heterocycles. The desired five-membered heterocyclic compounds were obtained in good to high yields at room temperature. The investigation of different solvents led us to the conclusion that water is the best solvent to perform the current one-pot, three-component reactions. Attempts to find the optimal catalyst loading clearly showed that 14 mg of cell-Pr-NH2 seems to be sufficient to carry out the reactions. This method has highlighted some principles of green chemistry including less waste generation, atom economy, use of water as an environmentally friendly solvent, and energy saving. Purification without chromatographic methods, mild reaction conditions, simple work-up, low-cost reaction medium, saving time, and obtainable precursors are other notable features of this one-pot fashion.

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Na₂S₂O₃ Catalyzed Three‐Component Synthesis and Anti‐Bacterial Activity of 3‐Methyl‐4‐(hetero)arylmethylene isoxazole‐5(4H)‐ones

Cited by 2 publications

References 36 publications

Antimicrobial activity of isoxazole derivatives: A brief overview

Antimicrobial activity of isoxazole derivatives: A brief overview

Synthesis of Isoxazol-5-One Derivatives Catalyzed by Amine-Functionalized Cellulose

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