Radical scavenging and anti-inflammatory activities of (hetero)arylethenesulfonyl fluorides: Synthesis and structure-activity relationship (SAR) and QSAR studies

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 OCH 3 ) groups on the phenyl ring possessed excellent antioxidant properties while compounds containing electron-withdrawing ( Cl, NO 2 , F and Br) groups on the phenyl ring were found to be most potent anti-inflammatory agents. The presence of SO 2 F group played a crucial role in increases both antioxidant and anti-inflammatory activities.