Synthesis of new 1-(4-methane(amino)sulfonylphenyl)-5-(4-substituted-aminomethylphenyl)-3-trifluoromethyl-1H-pyrazoles: A search for novel nitric oxide donor anti-inflammatory agents |
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| Institution: | 1. Pharmaceutical Organic Chemistry Department, Faculty of Pharmacy, Beni-Suef University, Beni-Suef, Egypt;2. Pharmacognosy Department, Faculty of Pharmacy, Beni-Suef University, Beni-Suef, Egypt;3. Faculty of Pharmacy and Pharmaceutical Sciences, University of Alberta, Edmonton, Alberta T6G 2N8, Canada;1. Department of Chemistry and Biochemistry, Brigham Young University, Provo, UT 84602, United States;2. Rega Institute for Medical Research, KU Leuven, B-3000 Leuven, Belgium;1. Department of Chemistry and Biochemistry, University of Arizona, Tucson, AZ 85721, USA;2. Department of Pharmacology, University of Arizona, Tucson, AZ 85721, USA;1. Laboratoire des Produits Naturels d’Origine Végétale et de Synthèse Organique, Faculté des Sciences Exactes, Campus de Chaabat Ersas, Université Constantine 1, Constantine 25000, Algeria;2. Unité de Recherche de Chimie de l’Environnement et Moléculaire Structurale, Université Constantine 1, Constantine 25000, Algeria;1. School of Chemical Sciences, North Maharashtra University, Jalgaon 425001, MS, India;2. Department of Chemistry, Indian Institute of Technology, Ropar, Rupnagar, Punjab, India |
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| Abstract: | A group of 1-(4-methane(amino)sulfonylphenyl)-5-(4-substituted-aminomethylphenyl)-3-trifluoromethyl-1H-pyrazoles (12a–f) was synthesized and evaluated as anti-inflammatory agents. While all the compounds (20 mg/kg) showed significant anti-inflammatory activity after 3 h of inflammation induction (69–89%) as compared to celecoxib (80%), 1-(4-methanesulfonylphenyl)-5-(4-methylaminomethylphenyl)-3-trifluoromethyl-1H-pyrazole (12a) was found to be the most effective one (89%). The synthesis of model hybrid nitric oxide donor N-diazen-1-ium-1,2-diolate derivatives of 1-(4-methanesulfonylphenyl)-5-(4-substituted-aminomethylphenyl)-3-trifluoromethyl-1H-pyrazoles (10a–f) requires further investigation since the reaction of N-(4-(1-(4-(methylsulfonyl)phenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)benzyl)ethanamine (12b) or 1-(4-(1-(4-(methylsulfonyl)phenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)benzyl)piperazine (12c) with nitric oxide furnished N-nitroso derivatives (13 and 14), respectively, rather than the desired N-diazen-1-ium-1,2-diolate derivatives (10b and 10c). |
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| Keywords: | Pyrazoles Cyclooxygenase Diazen-1-ium-1 2-diolate nitric oxide donors Anti-inflammatory activity |
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