Evaluation of sulfonamide derivatives of dagenan chloride as lipoxygenase and α-glucosidase inhibitors

Abstract

Purpose: To study the enzyme inhibition activity of various sulfonamides derived from dagenan chloride. Methods: The synthesis of N-(naphthalen-1-yl)-4-acetamidobenzenesulfonamide (3) was carried out by gearing up 1-naphthylamine (1) with dagenan chloride (2) in water in the presence of Na2CO3 solution. Further, compound 3 was treated with various alkyl/aralkyl halides (4a-o) to yield 5a-o in an aprotic polar solvent, DMF (dimethylformamide), using LiH as activator. The structures of all the synthesized molecules were corroborated by infra red spectroscopy (IR), proton nuclear magnetic resonance (1HNMR) and electron impact mass spectrometry (EI-MS) and screened against lipoxygenase and α- glucosidase using baicalein and acarbose as reference standards, respectively. Results: Molecules 5e and 5j showed good lipoxygenase inhibition activity with IC50 (50 % inhibition concentration) value of 132.21 ± 0.73 and 133.33 ± 0.87 μmol/L, respectively, relative to reference, while 5m was the most active inhibitor of α-glucosidase with IC50 of 19.41 ± 0.55 μmol/L relative to reference. Conclusion: Most of the synthesized compounds are good inhibitors of lipoxygenase but moderate inhibitors of α-glucosidase enzyme. These molecules should be evaluated for their in vivo activity to determine their potentials as anti-inflammatory and anti-diabetic drugs.