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

Affiliation

Atatürk University, Faculty of Science, Department of Chemistry, 25240 Erzurum, Turkey. Electronic address: [Email]

Abstract

In this paper, a series of novel bromophenol derivatives were synthesized and evaluated for their acetylcholinesterase and α-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⋅+) and 1,1-diphenyl-2-picryl-hydrazyl free radical (DPPH) 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 α-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 α-glycosidase.

Keywords

Acetylcholinesterase,Antioxidant activity,Bromophenols,Diarylmethanones, enzyme inhibition,α-glycosidase,

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