Synthesis and characterization of novel bromophenols: Determination of their anticholinergic, antidiabetic and antioxidant activities

In this paper, a series of novel bromophenol derivatives were synthesized and evaluated for their acetylcholinesterase and alpha-glycosidase enzymes inhibition properties and antioxidant activity. Diarylmethanones were synthesized and their bromination was carried out. During bromination, some compounds gave new bromophenols via regioselective O-demethylation. Demethylation of brominated diarylmethanones was also performed with BBr3 to give novel bromophenols. In addition, we examines the antioxidant capacity of novel bromophenol derivatives using several in vitro bioanalytical methodologies such as 2,2'-azino-bis(3-ethylbenzthiazoline-6-sulfonic acid) (ABTS center dot(+)) and 1,1-dipheny1-2-picryl-hydrazyl free radical (DPPH center dot) radical scavenging activity, Fe3+ and Cu2+ reducing activities and ferrous (Fe2+) ions chelating activities. Also, novel bromophenols and methoxylated bromophenols derivatives were tested against acetylcholinesterase and alpha-glycosidase, which associated with some metabolic diseases. The novel bromophenols showed Ki values in range of 8.94 +/- 0.73-59.45 +/- 14.97 nM against AChE and 4.31 +/- 1.93-44.14 +/- 2.19 nM against alpha-glycosidase.