A novel and efficient method for N-acylation of sulfonamides and carbamates: Their biological evaluation towards anti Malassezia activity

Abstract

BackgroundThe N-acylation of sulfonamides and carbamates with acid anhydrides in the presence of Lewis catalysis has been described. The N-acylation of various sulfonamides and carbamates with carboxylic acid anhydrides were effectively promoted by catalytic amount of CeCl3 under solvent-free conditions to produce the corresponding N-acyl products in good to excellent yields. The synthesized compounds were tested for their antifungal activity. MethodsTo a mixture of sulfonamide and anhydride, and anhydrous CeCl3 was added and the reaction was stirred for the given time. After completion of the reaction, the reaction mixture was diluted with dichloromethane and washed with water and brine solution. The combined organic layers were dried over Na2SO4 and evaporated in vacuum. The crude compound was purified by column chromatography to afford the corresponding N-acylated product. ResultsSynthesized compounds were screened for their antifungal activity against two virulent organisms Malassezia furfur and Malassezia pachydermatis. The compounds were tested in different concentrations ranging from 200 uM to 1 uM and taking their growth observations at OD 600 nm at different time intervals. The growth in the treated wells was compared with the growth in the untreated wells. Ketoconazole was used as control, among the compounds screened 2a, 2i and 4a showed activity than the standard antifungal drug i.e. Ketoconazole. ConclusionSynthesized compounds were evaluated for their antifungal activity and three compounds 2a, 2i, and 4a showed very good activity against both the organisms, for the first time N-acyl sulfonamides and carbamates classes were evaluated as potential anti-Malassezia agents.