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Triterpene-Based Carboxamides Act as Good Inhibitors of Butyrylcholinesterase

1
Martin-Luther-University Halle-Wittenberg, Organic Chemistry, Kurt-Mothes-Str. 2, D-06120 Halle (Saale), Germany
2
Leibniz Institute of Plant Biochemistry, Bioorganic Chemistry, Weinberg 3, D-06120 Halle (Saale), Germany
*
Author to whom correspondence should be addressed.
Academic Editors: Eva E. Rufino-Palomares and José Antonio Lupiáñez
Molecules 2019, 24(5), 948; https://doi.org/10.3390/molecules24050948
Received: 12 February 2019 / Revised: 25 February 2019 / Accepted: 2 March 2019 / Published: 7 March 2019
(This article belongs to the Special Issue Natural Products and Derivatives in Human Disorders)
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Abstract

A set of overall 40 carboxamides was prepared from five different natural occurring triterpenoids including oleanolic, ursolic, maslinic, betulinic, and platanic acid. All of which were derived from ethylene diamine holding an additional substituent connected to the ethylene diamine group. These derivatives were evaluated regarding their inhibitory activity of the enzymes acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) employing Ellman’s assay. We further determined the type of inhibition and inhibition constants. Carboxamides derived from platanic acid have been shown to be potent and selective BChE inhibitors. Especially the mixed-type inhibitor (3β)-N-(2-pyrrolidin-1-ylethyl)-3-acetyloxy-20-oxo-30-norlupan-28-amide (35) showed a remarkably low Ki of 0.07 ± 0.01 µM (Ki′ = 2.38 ± 0.48 µM) for the inhibition of BChE. View Full-Text
Keywords: acetylcholinesterase; butyrylcholinesterase; triterpenoids acetylcholinesterase; butyrylcholinesterase; triterpenoids
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Loesche, A.; Kahnt, M.; Serbian, I.; Brandt, W.; Csuk, R. Triterpene-Based Carboxamides Act as Good Inhibitors of Butyrylcholinesterase. Molecules 2019, 24, 948.

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