Design, synthesis and biological evaluation of 1,3-diaryltriazenesubstituted sulfonamides as antioxidant, acetylcholinesterase and butyrylcholinesterase inhibitors

Abstract

1,3-diaryltriazenes are one of the most useful and important linkers for many pharmaceuticalapplications. Therefore, in the current work, a series of 1,3-diaryltriazene sulfonamides 4(a-k) weresynthesized by reacting diazonium salt of sulfanylamide and substituted aromatic amine derivatives 3(ak). The obtained compounds were investigated for antioxidant properties by using different methods suchas a DPPH radical scavenging assay, ABTS radical decolarization, cupric reducing antioxidant capacity(CUPRAC) and metal chelating methods. The cholinesterase inhibition activities (acetylcholinesterase andbutyrylcholinesterase) of synthesized compounds were also tested. In general, compounds showed weakantioxidant activity, except compounds 4d (IC50 =114.89 µM for DPPH activity), 4i (IC50 =25.31 µM forABTS activity), 4a (IC50 = 86.33 µM for metal chelating activity), and 4k (absorbance value 1.229 µM forCUPRAC). Some of the compounds showed great % inhibition against both acetylcholinesterase andbutyrylcholinesterase with % inhibition values ranging from 11.54 to 93.67 and 62.24 to 98.47,respectively.