Chalcone derivatives bearing chromen or benzo[f]chromen moieties: Design,synthesis, and evaluations of anti-inflammatory,analgesic, selective COX-2 inhibitory activities |
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| Institution: | 1. Food and Pharmacy College, Zhejiang Ocean University, Zhejiang, Zhoushan 316022, PR China;2. Donghai Science and Technology College, Zhejiang Ocean University, Zhejiang, Zhoushan 316000, PR China;1. College of Pharmacy and Yonsei Institute of Pharmaceutical Sciences, Yonsei University, Incheon, Republic of Korea;2. Center for Drug Discovery Technology, Bio & Drug Discovery Division, Korea Research Institute of Chemical Technology, Daejeon, Republic of Korea;1. Pharmaceutical Chemistry Department, Faculty of Pharmacy, Cairo University, Kasr Elini St., Cairo 11562, Egypt;2. Pharmaceutical Chemistry Department, Faculty of Pharmacy, Badr University in Cairo, Badr City, Cairo 11829, Egypt;3. National Cancer Institute, Cairo University, FomElkhalig, Kasr Elaini St., Cairo 11796, Egypt;4. Pharmaceutical Chemistry Department, Faculty of Pharmacy, October University for Modern Sciences and Arts (MSA), Giza, Egypt;1. Department of Pharmaceutical Engineering, School of Chemistry, Chemical Engineering and Life Science, Wuhan University of Technology, 205 Luoshi Road, Wuhan, 430070, PR China;2. Department of Mathematics, Faculty of Science, King Abdulaziz University, Jeddah, 21589, Saudi Arabia;1. State Key Laboratory of Pharmaceutical Biotechnology, Nanjing University, Nanjing 210023, PR China;2. State Key Laboratory of Coordination Chemistry, Nanjing University, Nanjing 210023, PR China;3. Henan Provincial Key Laboratory of Children’s Genetics and Metabolic Diseases, Zhengzhou Children''s Hospital, Zhengzhou 450018, PR China;1. Department of Chemistry, Faculty of Pharmacy, Medical University of Sofia, 2, Dunav St., 1000 Sofia, Bulgaria;2. Institute of Microbiology, Bulgarian Academy of Sciences, 26, Acad. G. Bonchev St., 1113 Sofia, Bulgaria;3. Laboratory of Nuclear Magnetic Resonance, Institute of Organic Chemistry with Centre of Phytochemistry, Bulgarian Academy of Sciences, 9, Acad. G. Bonchev St., 1113 Sofia, Bulgaria;4. Laboratory of Experimental Chemotherapy, Department of Pharmacology, Pharmacotherapy and Toxicology, Faculty of Pharmacy, Medical University-Sofia, 2, Dunav St., 1000 Sofia, Bulgaria;5. Department of Physiology and Pharmacology “Vittorio Erspamer”, Sapienza University, P.le Aldo Moro 5, 00185 Rome, Italy;6. Department for Toxicology, Faculty of Pharmacy, University of Belgrade, 450, Vojvode Stepe, St., 11221 Belgrade, Serbia;7. Bulgarian Academy of Sciences, Institute of Mineralogy and Crystallography, 107, Acad. G. Bonchev St., 1113 Sofia, Bulgaria |
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| Abstract: | Thirty-eight chalcone derivatives bearing a chromen or benzof]chromen moiety were synthesized and evaluated for their anti-inflammatory and analgesic activities. Using an ear edema model, anti-inflammatory activities were observed for compounds 3a-3s (ear inflammation: 1.75–3.71 mg) and 4a-4s (ear inflammation: 1.71–4.94 mg). All compounds also displayed analgesic effects with inhibition values of 66.7–100% (3a-3s) and 96.2–100% (4a-4s). The 12 compounds that displayed excellent anti-inflammatory and analgesic effects were tested for their inhibitory activity against ovine COX-1 and COX-2. Six compounds bearing a chromen moiety were weak inhibitors of the COX-1 isozyme but showed moderate COX-2 isozyme inhibitory effects (IC50s from 0.37 μM to 0.83 μM) and COX-2 selectivity indexes (SI: 22.49–9.34). Those bearing a benzof]chromen moiety were more selective toward COX-2 than those bearing a chromen moiety with IC50s from 0.25 μM to 0.43 μM and COX-2 selectivity indexes from SI: 31.08 to 20.67. |
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| Keywords: | Chalcone derivatives Anti-inflammatory Analgesic COX-1/COX-2 |
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