The first synthesis and antioxidant and anticholinergic activities of 1-(4,5-dihydroxybenzyl)pyrrolidin-2-one derivative bromophenols including natural products

Authors : Mohsen REZAİ, Çetin BAYRAK, Parham TASLİMİ, İlhami GÜLÇİN, Abdullah MENZEK

Pages : 808-825

View : 16 | Download : 8

Publication Date : 0000-00-00

Article Type : Research Paper

Abstract :We report herein the first synthesis of biologically active natural bromophenols, namely 1-insert ignore into journalissuearticles values(2,3,6-tribromo-4,5-dihydroxybenzyl);pyrrolidin-2-one insert ignore into journalissuearticles values(2);, 2RS-1-insert ignore into journalissuearticles values(2,3-dibromo-4,5-dihydroxybenzyl);-5-oxopyrrolidine-2-carboxylic acid insert ignore into journalissuearticles values(3);, and 2RS-methyl 1-insert ignore into journalissuearticles values(2,3-dibromo-4,5-dihydroxybenzyl);-5-oxopyrrolidine-2-carboxylate insert ignore into journalissuearticles values(4);, along with their different derivatives insert ignore into journalissuearticles values(6 and 8-18);. Among the synthesized compounds, , 4, and their derivatives insert ignore into journalissuearticles values(8 and 9); are yielded in racemic form. Radical scavenging assays of the synthesized molecules were investigated using various bioanalytical antioxidant methods including 2,2`-azino-bis insert ignore into journalissuearticles values(3-ethylbenzothiazoline-6-sulfonic acid); insert ignore into journalissuearticles values(ABTS$^{\bullet +});$ and 2,2-diphenyl-1-picrylhydrazyl insert ignore into journalissuearticles values(DPPH$^{\bullet });$. In addition, the reducing power of the novel bromophenols was investigated by Cu$^{2+}$-Cu$^{+}$ reducing, Fe$^{3+}$-Fe$^{2+}$ reducing, and [Fe$^{3+}$-insert ignore into journalissuearticles values(TPTZ);$_{2}$]$^{3+}$-[Fe$^{2+}$-insert ignore into journalissuearticles values(TPTZ);$_{2}$]$^{2+}$ reducing capacity and ferrous ions insert ignore into journalissuearticles values(Fe$^{2+});$ chelating abilities. The molecules demonstrated powerful antioxidant activities when compared to standard antioxidant compounds of $\alpha $-tocopherol, trolox, butylated hydroxyanisole insert ignore into journalissuearticles values(BHA);, and butylated hydroxytoluene insert ignore into journalissuearticles values(BHT);. Moreover, novel bromophenols were tested against cholinergic enzymes including acetylcholinesterase insert ignore into journalissuearticles values(AChE); and butyrylcholinesterase insert ignore into journalissuearticles values(BChE); enzymes in the last part of this study. The presented novel bromophenols showed Ki values in the range of 2.60 $\pm $ 0.75-16.36 $\pm $ 2.67 nM against AChE and 13.10 $\pm $ 3.33-54.47 $\pm $ 13.53 nM against BChE.
Keywords : Bromination, bromophenol, pyrrolidin 2 one, natural product, antioxidant activity, acetylcholinesterase, butyrylcholinesterase