Novel antioxidant bromophenols with acetylcholinesterase, butyrylcholinesterase and carbonic anhydrase inhibitory actions

Abstract

In this study, a series of novel bromophenols were synthesized from benzoic acids and methoxylated bromophenols. The synthesized compounds were evaluated by using different bioanalytical antioxidant assays including 2,2-diphenyl-1-picrylhydrazyl (DPPH) and 2,2'-azino-bis (3-ethylbenzothiazoline-6-sul phonic acid) (ABTS(+)) radical scavenging assays. Also, reducing power of novel bromophenols were evaluated by Cu2+-Cu+ reducing, Fe3+-Fe2+ reducing and [Fe3+-(TPTZ)(2)](3+)-[Fe2+-(TPTZ)(2)](2+) reducing and ferrous ions (Fe2+) chelating abilities. The compounds demonstrate powerful antioxidant activities when compared to standard antioxidant molecules of alpha-tocopherol, trolox, butylated hydroxyanisole (BHA), and butylated hydroxytoluene (BHT). Also in the last part of this studies novel bromophenols were tested against some metabolic enzymes including acetylcholinesterase (AChE), butyrylcholinesterase (BChE) enzymes and carbonic anhydrase I, and II (hCA I and hCA II) isoenzymes. The newly synthesized bromophenols showed Ki values in a range of 6.78 +/- 0.68 to 126.07 +/- 35.6 nM against hCA I, 4.32 +/- 0.23 to 72.25 +/- 12.94 nM against hCA II, 4.60 +/- 1.15 to 38.13 +/- 5.91 nM against AChE and 7.36 +/- 1.31 to 29.38 +/- 3.68 nM against BChE. (C) 2017 Elsevier Inc. All rights reserved.