Substituted cinnamic anhydrides act as selective inhibitors of acetylcholinesterase.
作者： Josephine M. Gießel , Immo Serbian , Anne Loesche , René Csuk
DOI: 10.1016/J.BIOORG.2019.103058
关键词: Butyrylcholinesterase 、 Mixed type 、 Electric eel 、 Aché 、 Chemistry 、 Acetylcholinesterase 、 Enzyme 、 Reagent 、 Cytotoxic T cell 、 Stereochemistry
摘要: Abstract Cinnamic anhydrides have been shown to be more than reactive reagents, but they also act as inhibitors of the enzyme acetylcholinesterease (AChE). Thus, out a set 33 synthesised derivatives, several them were mixed type for AChE (from electric eel). (E)-3-(2,4-dimethoxyphenyl)acrylic anhydride (2c) showed Ki = 8.30 ± 0.94 µM and Ki′ = 9.54 ± 0.38 µM, (E)-3-(3-chlorophenyl)acrylic (2u) Ki = 8.23 ± 0.93 µM Ki′ = 13.07 ± 0.46 µM measured. While being not cytotoxic many human cell lines, these compounds an unprecedented noteworthy inhibitory effect butyrylcholinesterase (BChE).
sci-hub.se 参考文章(40)
Vernon L. Singleton, Paul Esau, Phenolic substances in grapes and wine,: And their significance ,(1969)
Hojatollah Khabazzadeh, Roohollah Moordini Nejad, Hassan Sheibani, Kazem Saidi, Solvent free microwave assisted Doebner reaction: A green method for the preparation of cinnamic acids Catalysis Communications. ,vol. 8, pp. 1411- 1413 ,(2007) , 10.1016/J.CATCOM.2006.11.036
George L. Ellman, K.Diane Courtney, Valentino Andres, Robert M. Featherstone, A new and rapid colorimetric determination of acetylcholinesterase activity Biochemical Pharmacology. ,vol. 7, pp. 88- 95 ,(1961) , 10.1016/0006-2952(61)90145-9
F. Benington, R. C. Morin, L. C. Clark, Jr., Notes - Mescaline Anaologs. VI. Mescaline Homologs Journal of Organic Chemistry. ,vol. 21, pp. 1545- 1546 ,(1956) , 10.1021/JO01118A635
Sophie Lafay, Angel Gil-Izquierdo, Bioavailability of phenolic acids Phytochemistry Reviews. ,vol. 7, pp. 301- 311 ,(2008) , 10.1007/S11101-007-9077-X
Shu-Fen Lin, Kenneth A. Connorsx, Kinetics of trans-Cinnamic Anhydride Reactions Catalyzed by Pyridine, 4-Dimethylaminopyridine, and N-Methylimidazole Journal of Pharmaceutical Sciences. ,vol. 70, pp. 235- 238 ,(1981) , 10.1002/JPS.2600700302
Touqeer Ahmed, Anwarul-Hassan Gilani, Inhibitory effect of curcuminoids on acetylcholinesterase activity and attenuation of scopolamine-induced amnesia may explain medicinal use of turmeric in Alzheimer's disease. Pharmacology, Biochemistry and Behavior. ,vol. 91, pp. 554- 559 ,(2009) , 10.1016/J.PBB.2008.09.010
Suresh, Dhruva Kumar, Jagir S. Sandhu, Bismuth(III) Chloride–Mediated, Efficient, Solvent-Free, MWI-Enhanced Doebner Condensation for the Synthesis of (E)-Cinnamic Acids Synthetic Communications. ,vol. 40, pp. 1915- 1919 ,(2010) , 10.1080/00397910903162833
O. Doebner, Synthese der Muconsäure aus Glyoxal und Malonsäure Berichte der deutschen chemischen Gesellschaft. ,vol. 35, pp. 1147- 1148 ,(1902) , 10.1002/CBER.190203501188
John R. Peterson, Morley E. Russell, Irawan B. Surjasasmita, Synthesis and experimental ionization energies of certain (E)-3-arylpropenoic acids and their methyl esters Journal of Chemical & Engineering Data. ,vol. 33, pp. 534- 537 ,(1988) , 10.1021/JE00054A042