Design, Ultrasonic-assisted Synthesis and Evaluation In vitro Antimicrobial Activity of Bis-isoxazole Derivatives Bearing Chloro-pyridinyl Group

doi:10.1007/s40242-021-0009-x

Chemical Research in Chinese Universities ›› 2021, Vol. 37 ›› Issue (3): 668-673.doi: 10.1007/s40242-021-0009-x

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Design, Ultrasonic-assisted Synthesis and Evaluation In vitro Antimicrobial Activity of Bis-isoxazole Derivatives Bearing Chloro-pyridinyl Group

FENG Fan¹, LI Jing¹, ZHANG Zhihui¹, FU Jiaxu¹, ZHANG Yumin^1,2, GU Qiang^1,2

1. College of Chemistry, Jilin University, Changchun 130012, P. R. China;
2. National-Local Joint Engineering Laboratory of In-situ Conversion, Drilling and Exploitation Technology for Oil Shale, Changchun 130021, P. R. China

Received:2021-01-05 Revised:2021-02-02 Online:2021-06-01 Published:2021-02-25
Contact: GU Qiang E-mail:guq@jlu.edu.cn
Supported by:
We are grateful to Dr. WANG Chunyu(College of Chemistry, Jilin University, China) for NMR spectra and Dr. WEI Zhonglin(College of Chemistry, Jilin University, China) for MS spectra.

Abstract

Abstract: An ultrasonic-assisted synthesis of bis-isoxazole derivatives was developed. Eight 3-(6-chloropyridin-3-yl)-5-{[(3-aryli-soxazol-5-yl)methoxy]methyl}isoxazoles were synthesized by 1,3-dipolar cycloaddition reaction between substituted isoxazolyl alkyne compounds and 6-chloro-N-hydroxynicotinimidoyl chloride. The structures of the synthesized compounds were confirmed by HRMS, FTIR, ¹H and ¹³C NMR spectroscopy. Wherein, the antifungal and antibacterial activities of target compounds were tested. The synthesized compounds 6a and 6h exhibited better antifungal activity in comparison with the standard drug itraconazole. The minimum inhibitory concentrations(MICs) of both compound 6a and compound 6h were both 4 μg/mL against Candida albicans ATCC 10231.

Key words: Ultrasonic-assisted, Bis-isoxazole, 1,3-Dipolar cycloaddi-tion, Antimicrobial activity

FENG Fan, LI Jing, ZHANG Zhihui, FU Jiaxu, ZHANG Yumin, GU Qiang. Design, Ultrasonic-assisted Synthesis and Evaluation In vitro Antimicrobial Activity of Bis-isoxazole Derivatives Bearing Chloro-pyridinyl Group[J]. Chemical Research in Chinese Universities, 2021, 37(3): 668-673.

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Design, Ultrasonic-assisted Synthesis and Evaluation In vitro Antimicrobial Activity of Bis-isoxazole Derivatives Bearing Chloro-pyridinyl Group

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