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

A series of novel bromophenol derivatives were synthesized and evaluated for their antioxidant, acetylcholinesterase, butyrylcholinesterase and carbonic anhydrase inhibitory properties. All synthesized compounds showed important activities. [Display omitted] •Series of novel bromophenol derivatives were synthesized.•Ferric ions (Fe3+) and cupric ions (Cu2+) reducing capacities were investigated.•The synthesized compounds showed ▪ and ▪ scavenging activities.•All compounds demonstrated inhibition against acetylcholinesterase and butyrylcholinesterase.•The synthesized compounds are hCA I and hCA II inhibitors. 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-sulphonic 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 α-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±35.6nM against hCA I, 4.32±0.23 to 72.25±12.94nM against hCA II, 4.60±1.15 to 38.13±5.91nM against AChE and 7.36±1.31 to 29.38±3.68nM against BChE.