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

高等学校化学研究 ›› 2021, Vol. 37 ›› Issue (3): 668-673.doi: 10.1007/s40242-021-0009-x

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

收稿日期:2021-01-05 修回日期:2021-02-02 出版日期:2021-06-01 发布日期:2021-02-25
通讯作者: GU Qiang E-mail:guq@jlu.edu.cn
基金资助:
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.

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.

摘要/Abstract

摘要： 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.

关键词: Ultrasonic-assisted, Bis-isoxazole, 1,3-Dipolar cycloaddi-tion, Antimicrobial activity

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]. 高等学校化学研究, 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

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

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