Design, Synthesis and Antibacterial Activities of 3-Methylcarbazole Derivatives Containing Isoxzole

doi:10.7503/cjcu20260151

Chem. J. Chinese Universities

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Design, Synthesis and Antibacterial Activities of 3-Methylcarbazole Derivatives Containing Isoxzole

YAN Yu^1#, LU Zicong^2#, WANG Qing², YANG Jiaqiang^2*

1. Department of Rehabilitation, The First Affiliated Hospital(Southwest Hospital) of Army Medical University 2. School of Pharmacy, Zunyi Medical University

Received:2026-04-14 Revised:2026-05-30 Online:2026-06-04 Published:2026-06-04
Supported by:
Supported by the Guizhou Provincial Science and Technology Plan Project of China(No. Qiankehe Foundation ZK[2024]265) and the National College Students' Innovation and Entrepreneurship Training Program(No. 202510661273)

1. ESM to 20260151.pdf(2230KB)

Abstract

Abstract: In order to obtain antibacterial candidate compounds, natural product 3-methylcarbazole was used as a hit compound for structural modification and optimization. A series of 3-methylcarbazole derivatives containing isoxazole moieties were designed and synthesized, and their structures were confirmed by 1H NMR, 13C NMR and elemental analysis. Antibacterial activity tests showed that these compounds exhibited significant activity against S. aureus, S. epidermidis and methicillin-resistant S. aureus(MRSA), with most derivatives demonstrating superior antibacterial activity compared to 3-Methylcarbazole. Among them, compound 3q was the most prominent, with minimum inhibitory concentration(MIC) values of 0.5, 1 and 2 μg·mL-1 against the three strains, respectively. Its anti-S. aureus and anti-S. epidermidis activities were comparable to those of the control drugs, while its anti-MRSA effect was significantly superior to that of the control drugs. The time–kill curve showed that compound 3q exerted rapid bactericidal activity against S. aureus throughout its entire growth cycle at 4×MIC. Molecular docking results revealed that compound 3q exhibited favorable binding interactions with the target protein GyrB. Additionally, compound 3q showed no toxicity toward mouse mononuclear macrophages. The introduction of the isoxazole moiety can enhance the antibacterial activity of 3-methylcarbazole.

Key words: 3-Methylcarbazole derivatives, Structural modification, Isoxzole, Synthesis, Antibacterial activity

CLC Number:

O626

TrendMD:

YAN Yu, LU Zicong, WANG Qing, YANG Jiaqiang. Design, Synthesis and Antibacterial Activities of 3-Methylcarbazole Derivatives Containing Isoxzole[J]. Chem. J. Chinese Universities, doi: 10.7503/cjcu20260151.

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Design, Synthesis and Antibacterial Activities of 3-Methylcarbazole Derivatives Containing Isoxzole

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