A facile reaction to access novel structural sulfonyl-hybridized imidazolyl ethanols as potential DNA-targeting antibacterial agents.

Bioorganic & Medicinal Chemistry Letters
Rammohan R Yadav BheemanaboinaCheng-He Zhou

Abstract

A novel type of sulfonyl-hybridized imidazolyl ethanols as potential DNA-targeting antibacterial agents was constructed via the unique ring-opened reaction of oxiranes by imidazoles for the first time. Some developed target hybrids showed potential antimicrobial potency against the tested microbes. Especially, imidazole derivative 5f could strongly suppressed the growth of MRSA (MIC = 4 μg/mL), which was 2-fold and 16-fold more potent than the positive control sulfathiazole and norfloxacin. This compound exhibited quite low propensity to induce bacterial resistance. Antibacterial mechanism exploration indicated that compound 5f could embed in MRSA DNA to form steady 5f-DNA complex, which possibly hinder DNA replication to exert antimicrobial behavior. Molecular docking showed that molecule 5f could bind with dihydrofolate synthetase through hydrogen bonds. These results implied that imidazole derivative 5f could be served as a promising molecule for the exploration of novel antibacterial candidates.

References

Feb 20, 2010·Analytical and Bioanalytical Chemistry·Rupak DoshiNicola Tirelli
Aug 17, 2010·European Journal of Medicinal Chemistry·Xian-Long WangCheng-He Zhou
Feb 11, 2012·Current Medicinal Chemistry·C-H Zhou, Y Wang
Feb 27, 2013·Current Pharmaceutical Design·Xin-Mei PengCheng- He Zhou
Jun 7, 2013·Medicinal Research Reviews·Ling ZhangCheng-He Zhou
Jul 31, 2013·Current Topics in Medicinal Chemistry·Xin-Mei PengCheng-He Zhou
Mar 21, 2016·European Journal of Medicinal Chemistry·Suresh NarvaVenkata Gowri Chandra Sekhar Kondapalli
Aug 4, 2016·Mini Reviews in Medicinal Chemistry·Hui-Zhen ZhangCheng-He Zhou
Nov 26, 2016·Chemical Communications : Chem Comm·Lijun XuRenjun Pei
May 12, 2017·European Journal of Medicinal Chemistry·Hui-Zhen ZhangCheng-He Zhou
Oct 21, 2017·Bioorganic & Medicinal Chemistry Letters·Xian-Fu FangCheng-He Zhou
Dec 31, 2017·European Journal of Medicinal Chemistry·Hui-Zhen ZhangCheng-He Zhou
May 20, 2018·European Journal of Medicinal Chemistry·Raquel Nunes da SilvaAugusto C Tomé
Jun 19, 2018·European Journal of Medicinal Chemistry·Yuan ZhangCheng-He Zhou
Feb 16, 2019·European Journal of Medicinal Chemistry·Liang-Liang WangCheng-He Zhou
Sep 12, 2020·Journal of Medicinal Chemistry·Minghui WangJianfeng Cai
May 18, 2021·Pesticide Biochemistry and Physiology·Yun-Peng XieCheng-He Zhou

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