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.
Highlights
It is more than a century since Alois Alzheimer, a German physician, described a new disease of the brain [1], being today one of the most threatening plagues for the elderly and one of the greatest challenges for chemists and biologists
A common strategy for the management of Alzheimer’s disease (AD) is to develop inhibitors that suppress the degradation of ACh caused by hydrolases acetylcholinesterase (AChE, EC 3.1.1.7)
Reagents and technical equipment were purchased in Germany unless otherwise stated
Summary
It is more than a century since Alois Alzheimer, a German physician, described a new disease of the brain [1], being today one of the most threatening plagues for the elderly and one of the greatest challenges for chemists and biologists. The eponymous disease is today one of the greatest scourges of humanity. Alzheimer’s disease (AD), the most common cause of dementia, is a neurodegenerative disorder, causing the progressive loss of cognitive functions and memory. As a result of demographic changes, the number of AD patients is steadily rising. This disease is characterized by an increasing decline in acetylcholine (ACh, neurotransmitter) levels in the cholinergic system [2]. A common strategy for the management of AD is to develop inhibitors that suppress the degradation of ACh caused by hydrolases acetylcholinesterase (AChE, EC 3.1.1.7)
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