Synthesis, Spectral Characterization and Antioxidant Activity of Novel Zafirlukast Sulfonyl Derivatives

A new series of cyclopentyl 3-(2-methoxy-4-(piperazine-1-carbonyl) benzyl)-1-methyl-1H-indol-5-ylcarbamate sulfonyl derivatives were synthesized by the reaclion of 4-((5-(cyclopentyloxycarbonylamino)-1-methyl-1H-indol-3-yl) methyl)-3-methoxybenzoic acid (ZAK drug intermediate) with Boc piperazine in the presence of EDC. HCl, HOBt, TEA in DMF followed by deboxylation by using 2N HCl or 35% HCl in acetone to get an intermediate compound. Further, this compound was treated with various substituted benzene sulfonyl chlorides in the presence of TEA in THF to afford title compounds. All the title compounds were characterized by (HNMR)-H-1, (CNMR)-C-13, IR and mass spectral data. The title compounds and starting material were evaluated for their antioxidant activity by using the DPPH, H2O2 and NO methods. The results revealed that some of the compounds have shown significant antioxidant activity.