New 1,2-diaryl-4-substituted-benzylidene-5-4H-imidazolone derivatives: Design,synthesis and biological evaluation as potential anti-inflammatory and analgesic agents |
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| Affiliation: | 1. Pharmaceutical Organic Chemistry Department, Faculty of Pharmacy, Beni-Suef University, Beni-Suef, Egypt;2. Pharmaceutical Sciences Department, Ibn Sina National College for Medical Studies, Jeddah 21418, Saudi Arabia;1. Helmholtz-Zentrum Dresden-Rossendorf, Institute of Radiopharmaceutical Cancer Research, Department Radiopharmaceutical and Chemical Biology, Bautzner Landstrasse 400, 01328 Dresden, Germany;2. Technische Universität Dresden, Department of Chemistry and Food Chemistry, 01069 Dresden, Germany;3. University of Rostock, Institute of Chemistry, Inorganic Solid State Chemistry, 18059 Rostock, Germany;1. Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Kafrelsheikh University, Kafrelsheikh, Egypt;2. Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Egyptian Russian University, Badr City, Cairo 11829, Egypt;3. Department of NEUROFARBA, Section of Pharmaceutical and Nutraceutical Sciences, University of Florence, Polo Scientifico, Via U. Schiff 6, 50019, Sesto Fiorentino, Firenze, Italy;4. Department of NEUROFARBA, Section of Pharmaceutical and Nutraceutical Sciences, Laboratory of Molecular Modeling Cheminformatics & QSAR, University of Florence, Polo Scientifico, Via U. Schiff 6, 50019, Sesto Fiorentino, Firenze, Italy;5. Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi Arabia;6. Department of Medicinal Chemistry, Faculty of Pharmacy, Mansoura University, Mansoura 35516, Egypt;1. Department of Pharmaceutical Chemistry, Himalayan Pharmacy Institute, Sikkim Central University, Majitar, Sikkim 737136, India;2. Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Jamia Hamdard University, New Delhi 110062, India;3. L.R. Institute of Pharmacy, Solan 173212, Himachal Pradesh, India;4. Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun 130022, PR China;1. Medicinal Chemistry Department, Faculty of Pharmacy, Minia University, Minia 61519, Egypt;2. Pharmaceutical Chemistry Department, Faculty of Pharmacy, Misr International University, Abbassia, 11566 Cairo, Egypt;3. Division of Medicinal Chemistry, College of Pharmacy, The University of Texas at Austin, Austin, TX 78712, USA |
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| Abstract: | A new series of 1,2-diaryl-4-substituted-benzylidene-5-4H-imidazolone derivatives 10a-h was designed and synthesized for evaluation as selective COX-2 inhibitors, anti-inflammatory agents and as analgesic agents. All compounds were more selective for COX-2 isozyme and showed good in vivo anti-inflammatory activity. Compounds 10a, 10b, 10e and 10f were the most COX-2 selective compounds (S.I. = 10.76, 10.87, 8.69 and 9.14 respectively), the most potent anti-inflammatory derivatives (ED50 = 65.7, 60.2, 76.3 and 107.4 μmol/kg respectively) in comparison with Celecoxib (COX-2 S.I. = 8.61, ED50 = 82.2 μmol/kg) and were less ulcerogenic (ulcer indexes = 1.22–3.02) than Ibuprofen (ulcer index = 20.25) and comparable to Celecoxib (ulcer index = 2.93). The four derivatives (10a, 10b, 10e and 10f) showed considerable analgesic activities which are clearly parallel to their anti-inflammatory activities. |
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| Keywords: | Anti-inflammatory Imidazolone Oxazolone Cyclooxygenase-2 inhibitors Analgesic |
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