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A facile reaction to access novel structural sulfonyl-hybridized imidazolyl ethanols as potential DNA-targeting antibacterial agents.
- Source :
-
Bioorganic & medicinal chemistry letters [Bioorg Med Chem Lett] 2021 Sep 01; Vol. 47, pp. 128198. Date of Electronic Publication: 2021 Jun 10. - Publication Year :
- 2021
-
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.<br /> (Copyright © 2021 Elsevier Ltd. All rights reserved.)
- Subjects :
- Anti-Bacterial Agents chemical synthesis
Anti-Bacterial Agents chemistry
Dose-Response Relationship, Drug
Ethanol chemical synthesis
Ethanol chemistry
Imidazoles chemistry
Microbial Sensitivity Tests
Molecular Structure
Structure-Activity Relationship
Anti-Bacterial Agents pharmacology
DNA, Bacterial drug effects
Ethanol pharmacology
Imidazoles pharmacology
Methicillin-Resistant Staphylococcus aureus drug effects
Subjects
Details
- Language :
- English
- ISSN :
- 1464-3405
- Volume :
- 47
- Database :
- MEDLINE
- Journal :
- Bioorganic & medicinal chemistry letters
- Publication Type :
- Academic Journal
- Accession number :
- 34119615
- Full Text :
- https://doi.org/10.1016/j.bmcl.2021.128198