Evaluation of Sulfonamide Derivatives of Dagenan Chloride as Lipoxygenase and α-Glucosidase Inhibitors

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 (1H-NMR) and electron impact mass spectrometry (EI-MS) and screened against lipoxygenase and alpha-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 mu mol/L, respectively, relative to reference, while 5m was the most active inhibitor of alpha-glucosidase with IC50 of 19.41 +/- 0.55 mu mol/L relative to reference. Conclusion: Most of the synthesized compounds are good inhibitors of lipoxygenase but moderate inhibitors of alpha-glucosidase enzyme. These molecules should be evaluated for their in vivo activity to determine their potentials as anti-inflammatory and anti-diabetic drugs.