Synthesis of some new pyrazolone derivatives as potent antimicrobial agents
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Date
2011
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Abstract
Invasive microbial infections are major problems around the world, especially in immuno compromised patients. The recent expansion of antimicrobial drug research has occurred because there is a critical need for new antimicrobial agents to treat these life threatening invasive infections. In the present study three series of new substituted pyrazolone derivatives (5a-f, 6a-f and 8a,b) were synthesized by the Knoevenagel condensation reaction of pyrazolones (3a,b) with various substituted carbaldehydes (4a-f, 7). These newly synthesized compounds were characterized by IR, NMR, mass spectra and also by C, H, N analyses. New compounds were screened for their antimicrobial studies against S. aureus, B. subtilis, E. coli and P. aeruginosa. The results revealed that compounds 5c and 6c having 2,5-dichlorothiophene substituent showed significant antibacterial activity against all tested microorganisms as compared to the standard drug Ceftriaxone.
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2 (2,4 dinitrophenyl) 4 [(6 methoxynaphthalen 2 yl)methylidene] 5 methyl 2,4 dihydro 3h pyrazol 3 one, 2 (2,4 dinitrophenyl) 4 [[3 (4 methoxyphenyl) 1h pyrazol 4 yl]methylidene] 5 methyl 2,4 dihydro 3h pyrazol 3 one, 2 (2,4 dinitrophenyl) 5 methyl 4 [[3 [4 (methylsulfanyl)phenyl] 1h pyrazol 4 yl]methylidene] 2,4 dihydro 3h pyrazol 3 one, 4 [(6 methoxynaphthalen 2 yl)methylidene] 5 methyl 2 phenyl 2,4 dihydro 3h pyrazol 3 one, 4 [[3 (2,4 dichlorophenyl) 1h pyrazol 4 yl]methylidene] 5 methyl 2 phenyl 2,4 dihydro 3h pyrazol 3 one, 4 [[3 (2,5 dichlorothiophen 3 yl) 1h pyrazol 4 yl]methylidene] 2 (2,4 dinitrophenyl) 5 methyl 2,4 dihydro 3h pyrazol 3 one, 4 [[3 (2,5 dichlorothiophen 3 yl) 1h pyrazol 4 yl]methylidene] 5 methyl 2 phenyl 2,4 dihydro 3h pyrazol 3 one, 4 [[3 (4 biphenyl) 1h pyrazol 4 yl]methylidene] 2 (2,4 dinitrophenyl) 5 methyl 2,4 dihydro 3h pyrazol 3 one, 4 [[3 (4 biphenyl) 1h pyrazol 4 yl]methylidene] 5 methyl 2 phenyl 2,4 dihydro 3h pyrazol 3 one, 4 [[3 (4 chlorophenyl) 1h pyrazol 4 yl]methylidene] 2 (2,4 dinitrophenyl) 5 methyl 2,4 dihydro 3h pyrazol 3 one, 4 [[3 (4 chlorophenyl) 1h pyrazol 4 yl]methylidene] 5 methyl 2 phenyl 2,4 dihydro 3h pyrazol 3 one, 4 [[3 (4 methoxyphenyl) 1h pyrazol 4 yl]methylidene] 5 methyl 2 phenyl 2,4 dihydro 3h pyrazol 3 one, 5 methyl 4 [[3 [4 (methylsulfanyl)phenyl] 1h pyrazol 4 yl]methylidene] 2 phenyl 2,4 dihydro 3h pyrazol 3 one, antibiotic agent, ceftriaxone, pyrazolone derivative, unclassified drug, antibacterial activity, article, Bacillus subtilis, carbon nuclear magnetic resonance, controlled study, drug determination, drug effect, drug screening, drug structure, drug synthesis, Escherichia coli, infrared spectroscopy, mass spectrometry, minimum inhibitory concentration, nitrogen nuclear magnetic resonance, nonhuman, proton nuclear magnetic resonance, Pseudomonas aeruginosa, Staphylococcus aureus
Citation
Der Pharma Chemica, 2011, 3, 4, pp. 454-463