Synthesis and antimicrobial activity of some novel quinoline-pyrazoline-based coumarinyl thiazole derivatives

A series of novel 3-(2-(5-(2-chloroquinolin-3-yl)-3-substituted phenyl-4,5-dihydro-1 H -pyrazol-1-yl)thiazol-4-yl)-6-H/halo-2 H -chromen-2-ones ( 9a–9y ) was prepared as antimicrobial agents by the condensation of 3-(2-bromoacetyl)-6-H/halo-2 H -chromen-2-ones ( 4a–4e ) and 5-(2-chloroquinolin-3-yl)...

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Bibliographic Details
Published in:Medicinal chemistry research 2017-07, Vol.26 (7), p.1481-1496
Main Authors: Ansari, Mohd. Imran, Khan, Suroor Ahmad
Format: Article
Language:English
Subjects:
Antifungal activity
Antiinfectives and antibacterials
Antimicrobial activity
Antimicrobial agents
Biochemistry
Biomedical and Life Sciences
Biomedicine
Cell Biology
Coumarin
Dilution
Ethanol
Fungicides
Infrared analysis
Ketoconazole
NMR
Nuclear magnetic resonance
Ofloxacin
Original Research
Pharmacology/Toxicology
Plates (structural members)
Pyrazole
Quinoline
Statistical analysis
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Summary:A series of novel 3-(2-(5-(2-chloroquinolin-3-yl)-3-substituted phenyl-4,5-dihydro-1 H -pyrazol-1-yl)thiazol-4-yl)-6-H/halo-2 H -chromen-2-ones ( 9a–9y ) was prepared as antimicrobial agents by the condensation of 3-(2-bromoacetyl)-6-H/halo-2 H -chromen-2-ones ( 4a–4e ) and 5-(2-chloroquinolin-3-yl)-3-substituted phenyl-4,5-dihydro-1 H -pyrazole-1-carbothiamide ( 8a–8e ) in ethanol. The structures of these compounds were confirmed on the basis of their infrared, 1 H-nuclear magnetic resonance, 13 C-nuclear magnetic resonance, mass and elemental analysis data. The antimicrobial activity of these compounds was determined by the serial plate dilution method. The compounds with fluoro-substituted coumarin ring along with the fluoro-substituted phenyl ring, 9q , 9r , and 9s , produced better and potent antimicrobial activity than their corresponding H/chloro/iodo/bromo-substituted analogs with statistically significant results ( p  
ISSN:1054-2523
1554-8120
DOI:10.1007/s00044-017-1855-4