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Synthesis of Brominated 2-phenitidine Derivatives As Valuable Inhibitors of Cholinesterases for the Treatment of Alzheimer's Disease

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Publisher Brieflands
Specialty Pharmacology
Date 2014 Apr 16
PMID 24734059
Citations 2
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Abstract

The present study reports the synthesis of a series N-substituted derivatives of brominated 2-phenitidine. First, the reaction of 2-phenitidine (1) with benzenesulfonyl chloride (2) in aqueous media yielded N-(2-ethoxyphenyl) benzenesulfonamide (3), which was then subjected to bromination with bromine in the presence of glacial acetic acid to give N-(4,5-dibromo-2-ethoxyphenyl) benzenesulfonamide (4). Secondly, the product (4) on further treatment with alkyl/aryl halides (5a-l) in the presence of lithium hydride (LiH) produced twelve new derivatives of N-substituted sulfonamides (6a-l). These were characterized by (1)H-NMR spectrum and screened against acetylcholinesterase (AChE), butyrylcholinesterase (BChE) and lipoxygenase (LOX) and were found to be valuable inhibitors of butyrylcholinesterase (BChE) and acetylcholinesterase (AChE). Few of them were also active against LOX.

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References
1.
Ye Q, Zhao W . New alloaromadendrane, cadinene and cyclocopacamphane type sesquiterpene derivatives and bibenzyls from Dendrobium nobile. Planta Med. 2002; 68(8):723-9. DOI: 10.1055/s-2002-33786. View

2.
Cygler M, Schrag J, Sussman J, Harel M, Silman I, Gentry M . Relationship between sequence conservation and three-dimensional structure in a large family of esterases, lipases, and related proteins. Protein Sci. 1993; 2(3):366-82. PMC: 2142374. DOI: 10.1002/pro.5560020309. View

3.
Clapp C, Banerjee A, Rotenberg S . Inhibition of soybean lipoxygenase 1 by N-alkylhydroxylamines. Biochemistry. 1985; 24(8):1826-30. DOI: 10.1021/bi00329a004. View

4.
Shi F, Tse M, Zhou S, Pohl M, Radnik J, Hubner S . Green and efficient synthesis of sulfonamides catalyzed by nano-Ru/Fe(3)O(4). J Am Chem Soc. 2009; 131(5):1775-9. DOI: 10.1021/ja807681v. View

5.
Oh S, Moon H, Son I, Jung J, Avery M . Synthesis of sulfonamides and evaluation of their histone deacetylase (HDAC) activity. Molecules. 2007; 12(5):1125-35. PMC: 6149482. DOI: 10.3390/12051125. View