Novel quinoline/thiazinan-4-one hybrids; design, synthesis, and molecular docking studies as potential anti-bacterial candidates against MRSA.
| Autor: | Mohamed AH; Chemistry Department, Faculty of Science, Minia University El-Minia 61519 Egypt asmaa.hamouda@mu.edu.eg sara.ahmed@mu.edu.eg ashrafaly63@yahoo.com ashraf.shehata@mu.edu.eg alaahassan2001@mu.edu.eg esraamah33@gmail.com., Mostafa SM; Chemistry Department, Faculty of Science, Minia University El-Minia 61519 Egypt asmaa.hamouda@mu.edu.eg sara.ahmed@mu.edu.eg ashrafaly63@yahoo.com ashraf.shehata@mu.edu.eg alaahassan2001@mu.edu.eg esraamah33@gmail.com., Aly AA; Chemistry Department, Faculty of Science, Minia University El-Minia 61519 Egypt asmaa.hamouda@mu.edu.eg sara.ahmed@mu.edu.eg ashrafaly63@yahoo.com ashraf.shehata@mu.edu.eg alaahassan2001@mu.edu.eg esraamah33@gmail.com., Hassan AA; Chemistry Department, Faculty of Science, Minia University El-Minia 61519 Egypt asmaa.hamouda@mu.edu.eg sara.ahmed@mu.edu.eg ashrafaly63@yahoo.com ashraf.shehata@mu.edu.eg alaahassan2001@mu.edu.eg esraamah33@gmail.com., Osman EM; Chemistry Department, Faculty of Science, Minia University El-Minia 61519 Egypt asmaa.hamouda@mu.edu.eg sara.ahmed@mu.edu.eg ashrafaly63@yahoo.com ashraf.shehata@mu.edu.eg alaahassan2001@mu.edu.eg esraamah33@gmail.com., Nayl AA; Department of Chemistry, College of Science, Jouf University Sakaka 72341 Aljouf Saudi Arabia aanayel@ju.edu.sa., Brown AB; Chemistry Department, Florida Institute of Technology Melbourne FL USA., Abdelhafez EMN; Department of Medicinal Chemistry, Faculty of Pharmacy, Minia University 61519 Minia Egypt. |
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| Jazyk: | angličtina |
| Zdroj: | RSC advances [RSC Adv] 2023 May 12; Vol. 13 (21), pp. 14631-14640. Date of Electronic Publication: 2023 May 12 (Print Publication: 2023). |
| DOI: | 10.1039/d3ra01721d |
| Abstrakt: | In an attempt to develop effective and safe antibacterial agents, we synthesized novel thiazinanones by combining the quinolone scaffold and the 1,3-thiazinan-4-one group by reaction between ((4-hydroxy-2-oxo-1,2-dihydroquinolin-3-yl)methylene)hydrazinecarbothioamides and 2,3-diphenylcycloprop-2-enone in refluxing ethanol in the presence of triethyl amine as a catalyst. The structure of the synthesized compounds was characterized by spectral data and elemental analysis, IR, MS, 1 H and 13 C NMR spectroscopy which showed two doublet signals for CH-5 and CH-6 and four sharp singlets for the protons of thiazinane NH, CH[double bond, length as m-dash]N, quinolone NH and OH, respectively. Also, the 13 C NMR spectrum clearly showed the presence of two quaternary carbon atoms which were assigned to thiazinanone-C-5 and C-6. All the 1,3-thiazinan-4-one/quinolone hybrids were screened for antibacterial activity. Compounds 7a, 7e and 7g showed broad spectrum antibacterial activity against most of the tested strains either G +ve or G -ve. Compound 7e is the most potent antibacterial agent against MRSA with the minimum inhibitory concentration against MRSA found to be 48 μg mL -1 compared to the drug ciprofloxacin (96 μg mL -1 ). Additionally, a molecular docking study was performed to understand the molecular interaction and binding mode of the compounds on the active site of S. aureus Murb protein. In silico docking assisted data strongly correlated with the experimental approach of antibacterial activity against MRSA. Competing Interests: The authors declare no conflict of interest. The authors declare that they have no known competing interests. (This journal is © The Royal Society of Chemistry.) |
| Databáze: | MEDLINE |
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