Novel pyrazole integrated 1,3,4-oxadiazoles: Synthesis,characterization and antimicrobial evaluation |
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| Institution: | 1. Department of Chemistry, Yuvaraja’s College, University of Mysore, Mysore 570 005, India;2. Department of Studies in Chemistry, Manasagangotri, University of Mysore, India;3. Department of Biotechnology, Manasagangotri, University of Mysore, Mysore 570 006, India;1. Department of Chemistry, Faculty of Science, Banaras Hindu University, Varanasi 221 005, India;2. Department of Pharmacology, IMS, Banaras Hindu University, Varanasi 221 005, India;3. Amrita Centre for Nanosciences and Molecular Medicine (ACNSMM), Amrita Institute of Medical Sciences & Research Centre, Ponekkara, Kochi 682 041, Kerala State, India;1. Dipartimento di Chimica e Tecnologie del Farmaco, Università ‘La Sapienza’, P.le Aldo Moro, 5, 00185 Rome, Italy;2. Dipartimento di Scienze Biomediche, Università di Cagliari, 09042 Monserrato, Cagliari, Italy;1. Department of Chemistry, Faculty of Arts and Sciences, Dumlupinar University, 43100 Kutahya, Turkey;2. Department of Biology, Faculty of Arts and Sciences, Dumlupinar University, 43100 Kutahya, Turkey;3. Department of Physics, Fatih University, 34500 B. Cekmece, Istanbul, Turkey;4. School of Earth Sciences, The Ohio State University, 43210 Columbus, OH, USA;1. Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi Arabia;2. Department of Applied Organic Chemistry, National Research Center, Dokki, Cairo 12622, Egypt;3. Department of Pharmacology, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi Arabia;4. Department of Pharmacology, Faculty of Pharmacy, Mansoura University, P.O. Box 35516, Mansoura, Egypt |
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| Abstract: | A novel series of 2-(5-methyl-1,3-diphenyl-1H-pyrazol-4-yl)-5-phenyl-1,3,4-oxadiazoles 7(a–m) were synthesized either by cyclization of N′-benzoyl-5-methyl-1,3-diphenyl-1H-pyrazole-4-carbohydrazide 4a using POCl3 at 120 °C or by oxidative cyclization of hydrazones derived from various arylaldehyde and (E)-N′-benzylidene-5-methyl-1,3-diphenyl-1H-pyrazole-4-carbohydrazide 5(a–d) using chloramine-T as oxidant. Newly synthesized compounds were characterized by analytical and spectral (IR, 1H NMR, 13C NMR and LC–MS) methods. The synthesized compounds were evaluated for their antimicrobial activity and were compared with standard drugs. The compounds demonstrated potent to weak antimicrobial activity. Among the synthesized compounds, compound 7m emerged as an effective antimicrobial agent, while compounds 7d, 7f, 7i and 7l showed good to moderate activity. The minimum inhibitory concentration of the compounds was in the range of 20–50 μg mL?1 against bacteria and 25–55 μg mL?1 against fungi. The title compounds represent a novel class of potent antimicrobial agents. |
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| Keywords: | Pyrazole 1 3 4-Oxadiazoles Chloramine-T Antimicrobial activity Minimum inhibitory concentration (MIC) |
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