Synthesis, characterization and antimicrobial studies of some new pyrazole incorporated imidazole derivatives
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Date
2011
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Abstract
In the present study two series of novel imidazole derivatives containing substituted pyrazole moiety (3a-d and 5a-j) were synthesized. The first series were synthesized by the reaction of 3-aryl-1H-pyrazole-4-carbaldehyde thiosemicarbazones (2a-d) with DMAD and the second series by the reaction of 3-aryl-1H-pyrazole-4-carbaldehydes (1a-e) with 1,2-diketones (4a,b) in the presence of ammonium acetate. Structures of newly synthesized compounds were characterized by spectral studies. New compounds were screened for antifungal and antibacterial activities. Among the synthesized compounds, compound 3c was found to be potent antimicrobial agent. The acute oral toxicity study for the compound 3c was carried out and the experimental studies revealed that compound 3c is safe up to 3000 mg/kg and no death of animals were recorded. © 2011 Elsevier Masson SAS. All rights reserved.
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3 (2,4 dichlorophenyl) 4 (4,5 diphenyl 1h imidazol 2 yl) 1h pyrazole, 3 (2,5 dichlorothiophen 3 yl) 4 (4,5 diphenyl 1h imidazol 2 yl) 1h pyrazole, 3 (biphenyl 4 yl) 4 (4,5 diphenyl 1h imidazol 2 yl) 1h pyrazole, 3 (biphenyl 4 yl) 4 [4,5 bis(4 bromophenyl) 1h imidazol 2 yl] 1h pyrazole, 4 (4,5 diphenyl 1h imidazol 2 yl) 3 (4 methylphenyl) 1h pyrazole, 4 (4,5 diphenyl 1h imidazol 2 yl) 3 [4 (methylsulfanyl)phenyl] 1h pyrazole, 4 [4,5 bis(4 bromophenyl) 1h imidazol 2 yl] 3 (2,4 dichlorophenyl) 1h pyrazole, 4 [4,5 bis(4 bromophenyl) 1h imidazol 2 yl] 3 (2,5 dichlorothiophen 3 yl) 1h pyrazole, 4 [4,5 bis(4 bromophenyl) 1h imidazol 2 yl] 3 (4 methylphenyl) 1h pyrazole, 4 [4,5 bis(4 bromophenyl) 1h imidazol 2 yl] 3 [4 (methylsulfanyl)phenyl] 1h pyrazole, antiinfective agent, fluconazole, imidazole derivative, m ethyl 2 [5 oxo 2 thioxo 3 [[3 (4 tolyl)] 1h pyrazol 4 yl]methyleneamino]imidazolidin 4 ylidene)acetate, methyl 2 [3 [[3 (2,4 dichlorophenyl) 1h pyrazol 4 yl]methyleneamino] 5 oxo 2 thioxoimidazolidin 4 ylidene]acetate, methyl 2 [3 [[3 (2,5 dichlorothiophen 3 yl) 1h pyrazol 4 yl]methyleneamino] 5 oxo 2 thioxoimidazolidin 4 ylidene]acetate, methyl 2 [3 [[3 [4 (methylthio)phenyl] 1h pyrazol 4 yl]methyleneamino] 5 oxo 2 thioxoimidazolidin 4 ylidene]acetate, pyrazole derivative, unclassified drug, animal behavior, animal experiment, antibacterial activity, antifungal activity, Arthroderma gypseum, article, Aspergillus flavus, Aspergillus niger, Bacillus subtilis, Candida albicans, Clostridium perfringens, concentration response, drug potency, drug safety, drug structure, drug synthesis, Escherichia coli, female, in vitro study, mouse, nonhuman, Pseudomonas aeruginosa, Salmonella typhimurium, Staphylococcus aureus, structure activity relation, Trichophyton rubrum, Administration, Oral, Animals, Anti-Infective Agents, Bacterial Infections, Female, Fungi, Gram-Negative Bacteria, Gram-Positive Bacteria, Imidazoles, Maximum Tolerated Dose, Mice, Microbial Sensitivity Tests, Molecular Structure, Mycoses, Pyrazoles
Citation
European Journal of Medicinal Chemistry, 2011, 46, 8, pp. 3531-3536