Radical scavenging and anti-inflammatory activities of (hetero)arylethenesulfonyl fluorides: Synthesis and structure-activity relationship (SAR) and QSAR studies |
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| Institution: | 1. Department of Pharmaceutical Engineering, School of Chemistry, Chemical Engineering and Life Science, Wuhan University of Technology, 205 Luoshi Road, Wuhan 430073, PR China;2. Biotechnology Research Group, Deportment of Biological Sciences, Faculty of Science, King Abdulaziz University, Jeddah, Saudi Arabia;3. Department of Biotechnology, Adichunchanagiri University, B.G. Nagara, Mandya 571448, Karnataka, India;4. Department of Chemistry, Sri Jayachamarajendra College of Engineering, Mysuru 570006, Karnataka, India;5. Department of Biochemistry, Faculty of Applied Science College, University of Hajjah, Yemen;1. Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, Karnataka, India;2. Department of Chemistry, KLE Society''s Jagadguru Tontadarya College, Gadag-582101, Karnataka, India;1. Department of Pharmacy, Federal University of Juiz de Fora (UFJF), Campus Governador Valadares, MG, Brazil;2. Department of Pharmaceutical Sciences, Federal University of Santa Catarina (UFSC), Florianópolis, SC, Brazil;3. Department of Chemistry, Federal University of Santa Catarina (UFSC), Florianópolis, SC, Brazil;4. UMYMFOR-CONICET, Department of Organic Chemistry, University of Buenos Aires, Buenos Aires, Argentina;5. Theoretical Medicinal and Environmental Chemistry Laboratory (LQMAT), Department of Pharmacy, Western Paraná State University (Unioeste), Cascavel, PR, Brazil;1. Department of Chemistry, Sri Jayachamarajendra College of Engineering, Mysuru-570 006, Karnataka, India;2. Department of Studies in Biotechnology, University of Mysore, Manasagangotri, Mysuru-570006, Karnataka, India;3. Research and Development Centre, Bharathiar University, Coimbatore-641046, Tamil Nadu, India;4. Ganesh Consultancy and Analytical Services, Hebbal Industrial Area, Mysore-570016, Karnataka, India;5. Sri Ram Chem, R & D Centre, Plot No. 31, JCK Industrial Park, Belagola Industrial Area, Mysore 570016, Karnataka, India;6. PG Department of Chemistry, JSS College of Arts, Commerce and Science, Mysuru-570 025, Karnataka, India;7. Department of Pharmaceutical Engineering, School of Chemistry, Chemical Engineering and Life Science, Wuhan University of Technology, 205 Luoshi Road, Wuhan, 430073, PR China;1. Department of Pharmaceutical Engineering, School of Chemistry, Chemical Engineering and Life Science, Wuhan University of Technology, 205 Luoshi Road, Wuhan, 430073, PR, China;2. Department of Chemistry, Sri Jayachamarajendra College of Engineering, Mysuru, 570006, Karnataka, India;3. Department of Biochemistry, Faculty of Applied Science College, University of Hajjah, Yemen |
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| Abstract: | A series of (hetero)arylethenesulfonyl fluorides (1–58) were synthesized and screened for their in vitro antioxidant (DPPH, ABTS and DMPD methods) and anti-inflammatory activities. The results revealed that compounds 4, 15, 16, 24, 25, 26, 38, 39, 40, and 54 exhibited excellent antioxidant activity using all the three performed antioxidant methods, which were superior to the standard antioxidants ascorbic acid and gallic acid. Compounds 6–9, 11, 18, 19, 21, 22, 30, 39, 40, 44, 45, 48–50, 54, 55 and 57 displayed promising anti-inflammatory activity, which were better than the reference drug indomethacin. Preliminary structure–activity relationship (SAR) revealed that compounds containing electron donating ( OH and OCH3) groups on the phenyl ring possessed excellent antioxidant properties while compounds containing electron-withdrawing (Cl, NO2, F and Br) groups on the phenyl ring were found to be most potent anti-inflammatory agents. The presence of SO2F group played a crucial role in increases both antioxidant and anti-inflammatory activities. |
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| Keywords: | (hetero)arylethenesulfonyl fluorides DPPH ABTS DMPD Anti-inflammatory activity SAR studies |
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