Synthesis and antimicrobial evaluation of 1-(benzofuran-2-yl)-4-nitro-3-arylbutan-1-ones and 3-(benzofuran-2-yl)-4,5-dihydro-5-aryl-1-[4-(aryl)-1, 3-thiazol-2-yl]-1H-pyrazoles

2-Acetylbenzofuran 1 on treatment with substituted aldehydes affords the corresponding chalcones 2a-c. Treatment of the chalcones with nitromethane under Michael addition condition furnished the corresponding Michael adducts 3a-c. Cyclocondensation of the chalcones 2a and 2b with thiosemicarbazide u...

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Bibliographic Details
Published in:European journal of medicinal chemistry 2009-06, Vol.44 (6), p.2632-2635
Main Authors: ABDEL-WAHAB, Bakr F, ABDEL-AZIZ, Hatem A, AHMED, Essam M
Format: Article
Language:English
Subjects:
Anti-Bacterial Agents - chemical synthesis
Anti-Bacterial Agents - chemistry
Anti-Bacterial Agents - pharmacology
Antibacterial agents
Antibiotics. Antiinfectious agents. Antiparasitic agents
Antifungal agents
Antifungal Agents - chemical synthesis
Antifungal Agents - chemistry
Antifungal Agents - pharmacology
Aspergillus niger - drug effects
Bacillus subtilis - drug effects
Benzofurans - chemical synthesis
Benzofurans - chemistry
Benzofurans - pharmacology
Biological and medical sciences
Candida albicans - drug effects
Chalcones - chemistry
Cyclization
Dose-Response Relationship, Drug
Drug Design
Escherichia coli - drug effects
General aspects
Medical sciences
Microbial Sensitivity Tests
Molecular Structure
Pharmacology. Drug treatments
Pyrazoles - chemical synthesis
Pyrazoles - chemistry
Pyrazoles - pharmacology
Staphylococcus aureus - drug effects
Stereoisomerism
Structure-Activity Relationship
Thioamides - chemical synthesis
Thioamides - chemistry
Thioamides - pharmacology
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Summary:2-Acetylbenzofuran 1 on treatment with substituted aldehydes affords the corresponding chalcones 2a-c. Treatment of the chalcones with nitromethane under Michael addition condition furnished the corresponding Michael adducts 3a-c. Cyclocondensation of the chalcones 2a and 2b with thiosemicarbazide under basic refluxing conditions gave 3-(benzofuran-2-yl)-5-(4-aryl)-4,5-dihydropyrazole-1-carbothioamides 4a,b. The pyrazolines 7a-d were synthesized by treating 4a,b with phenacyl bromides in refluxing ethanol. All the synthesized compounds were screened for their antibacterial and antifungal activities at 100 microg concentration. Some of our compounds showed excellent antimicrobial activities than control drugs.
ISSN:0223-5234
1768-3254
DOI:10.1016/j.ejmech.2008.09.029