Synthesis, characterization and antibacterial activity of 2-[1-(5-chloro-2-methoxy-phenyl)-5-methyl-1H-pyrazol-4-yl]-5-(substituted-phenyl)-[1,3,4]oxadiazoles |
| |
Authors: | Neithnadka Premsai Rai Venugopala Katharigatta Narayanaswamy Sheena Shashikanth Pirama Nayagam Arunachalam |
| |
Institution: | aDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India;bDepartment of Pharmaceutical Chemistry, Al-Ameen College of Pharmacy, Hosur Road, Opp. Lalbagh Main Gate, Bangalore 560 027, Karnataka, India;cSyngene International Ltd., Biocon Park, Plot #2 and 3, Bommasandra – Jigani Road, Bangalore 560 099, Karnataka, India |
| |
Abstract: | In the present investigation a series of novel 2-1-(5-chloro-2-methoxy-phenyl)-5-methyl-1H-pyrazol-4-yl]-5-(substituted-phenyl)-1,3,4]oxadiazoles (4a–j) were synthesized by cyclization of substituted-benzoic acid N′-1-(5-chloro-2-methoxy-phenyl)-5-methyl-1H-pyrazole-4-carbonyl]-hydrazide by using phosphorousoxychloride at 120 °C. The chemical structure of the newly synthesized compounds was characterized by analytical and spectral (IR, 1H NMR, 13C NMR and LC–MS) methods. The title compounds were screened for qualitative (zone of inhibition) and quantitative antibacterial activity (MIC) by agar cup plate and microtitration methods, respectively. Among the synthesized compounds in this series compound 2-1-(5-chloro-2-methoxyphenyl)-5-methyl-1H-pyrazol-4-yl]-5-(4-fluorophenyl)-1,3,4-oxadiazole (4b) was found to exhibit significant antibacterial activity with MICs of 22.4, 29.8, 29.6 and 30.0 μg/mL against Bacillus subtilis, Staphylococcus aureus, Escherichia coli and Klebsiella pneumoniae, respectively. The other compounds exhibited moderate activity when compared to standard substance Ampicillin. |
| |
Keywords: | 2-[1-(5-Chloro-2-methoxy-phenyl)-5-methyl-1H-pyrazol-4-yl]-5-(substituted-phenyl)-[1 3 4]oxadiazoles Antibacterial activity Minimum inhibitory concentration |
本文献已被 ScienceDirect 等数据库收录! |
|