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Dergiler / Turkish Journal of Chemistry / 2018 / Cilt: 42 - Sayı: 3

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

Abdullah MENZEK
İlhami GÜLÇİN
Mohsen REZAI
Çetin BAYRAK
Parham TASLIMI
Sayfa
808–825
Yayın Tarihi
2022-11-05
DOI
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The presented novel bromophenols showed Kivalues in the range of 2.60 ± 0.75–16.36 ± 2.67 nM against AChE and 13.10 ± 3.33–54.47 ± 13.53 nM against BChE.

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Amaç & Hipotez:We report herein the first synthesis of biologically active natural bromophenols, namely 1-(2,3,6-tribromo-4,5-dihydroxybenzyl)pyrrolidin-2-one (2), 2RS-1-(2,3-dibromo-4,5-dihydroxybenzyl)-5-oxopyrrolidine-2-carboxylic acid(3), and 2RS-methyl 1-(2,3-dibromo-4,5-dihydroxybenzyl)-5-oxopyrrolidine-2-carboxylate (4), along with their differentderivatives (6 and 8–18).
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Temel Bulgular & Veri:Among the synthesized compounds, 3, 4, and their derivatives (8 and 9) are yielded inracemic form.
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Sonuç & Katkı:The presented novel bromophenols showed Kivalues in the range of 2.60 ± 0.75–16.36 ± 2.67 nM against AChE and 13.10 ± 3.33–54.47 ± 13.53 nM against BChE.
🔬Tür:Araştırma Makalesi
📍Kapsam:Genişletilmiş Akademik Örneklem
⚙️Değişkenler:Alan Parametreleri

Abstract

We report herein the first synthesis of biologically active natural bromophenols, namely 1-(2,3,6-tribromo-4,5-dihydroxybenzyl)pyrrolidin-2-one (2), 2RS-1-(2,3-dibromo-4,5-dihydroxybenzyl)-5-oxopyrrolidine-2-carboxylic acid(3), and 2RS-methyl 1-(2,3-dibromo-4,5-dihydroxybenzyl)-5-oxopyrrolidine-2-carboxylate (4), along with their differentderivatives (6 and 8–18). Among the synthesized compounds, 3, 4, and their derivatives (8 and 9) are yielded inracemic form. Radical scavenging assays of the synthesized molecules were investigated using various bioanalyticalantioxidant methods including 2,2’-azino-bis (3-ethylbenzothiazoline-6-sulfonic acid) (ABTS • +) and 2,2-diphenyl-1-picrylhydrazyl (DPPH • ). In addition, the reducing power of the novel bromophenols was investigated by Cu 2+ –Cu + reducing, Fe 3+ –Fe 2+ reducing, and [Fe 3+ –(TPTZ) 2 ] 3+ –[Fe 2+ –(TPTZ) 2 ] 2+ reducing capacity and ferrous ions(Fe 2+) chelating abilities. The molecules demonstrated powerful antioxidant activities when compared to standardantioxidant compounds of α -tocopherol, trolox, butylated hydroxyanisole (BHA), and butylated hydroxytoluene (BHT).Moreover, novel bromophenols were tested against cholinergic enzymes including acetylcholinesterase (AChE) andbutyrylcholinesterase (BChE) enzymes in the last part of this study. The presented novel bromophenols showed Kivalues in the range of 2.60 ± 0.75–16.36 ± 2.67 nM against AChE and 13.10 ± 3.33–54.47 ± 13.53 nM against BChE.

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Bu Makaleye Atıf Yap

MENZEK, A., GÜLÇİN, İ., REZAI, M., BAYRAK, Ç., TASLIMI, P. (2022). The first synthesis and antioxidant and anticholinergic activities of 1-(4,5-dihydroxyb enzyl)pyrrolidin-2-one derivative bromophenols including natural products. Turkish Journal of Chemistry, Cilt: 42 - Sayı: 3, 808–825. https://ajindex.com/articles/601999

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