Novel dehydroabietylamine derivatives as potent inhibitors of acetylcholinesterase

Wiemann, Jana; Csuk, René; Csük, René

doi:10.1016/j.bioorg.2017.07.013

Cited by 31 publications

(21 citation statements)

References 23 publications

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“…It has been reported that furan ring structures can participate in benzoxazine crosslinking reactions and improve the crosslinking density of the system . Dehydroabietylamine is widely used in the fields of dyes, coatings, photochemical resolution, metal processing, and other fine processing . Recently, our group also successfully synthesized two fully bio‐based benzoxazines using dehydroabietylamine .…”

Section: Introductionmentioning

confidence: 99%

“…30,[34][35][36][37] Dehydroabietylamine is widely used in the fields of dyes, coatings, photochemical resolution, metal processing, and other fine processing. [38][39][40][41][42][43] Recently, our group also successfully synthesized two fully bio-based benzoxazines using dehydroabietylamine. 44 This is also the first application of dehydroabietylamine in the field of benzoxazine research.…”

Section: Introductionmentioning

confidence: 99%

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Bio‐based benzoxazines based on sesamol: Synthesis and properties

Liu

Zhan

et al. 2019

J of Applied Polymer Sci

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Sesamol was used with furfurylamine, dehydroabietylamine, and stearylamine to prepare three fully‐bio‐based benzoxazines: S‐fa, S‐da, and S‐sa, respectively. Their structures were confirmed by Fourier transform infrared spectroscopy (FTIR), 1H‐NMR, and 13C‐NMR. FTIR and differential scanning calorimetry were performed to monitor the curing behaviors of S‐fa, S‐da, and S‐sa. The thermal stability of the corresponding polybenzoxazines was supported by thermogravimetric analysis, and all polymers showed high thermal stability. The limiting oxygen indexes of all three polybenzoxazines were higher than 30, suggestive of good flame retardancy. The use of polybenzoxazine for the corrosion protection of Q235 low‐carbon steel was also studied. The results of OCP curves and Tafel plots demonstrate that the polymer coatings provide good corrosion resistance and can be applied to this purpose. © 2019 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2019, 136, 48255.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Bio‐based benzoxazines based on sesamol: Synthesis and properties

Liu

Zhan

et al. 2019

J of Applied Polymer Sci

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“…Alzheimer's disease (AD) is the most common progressive and multifaceted neurodegenerative disease, with clinical manifestations of memory loss and cognitive impairment. 1) World Alzheimer's Report showed that in 2015 there were about 50 million Alzheimer's patients all over the world and the number of AD cases was estimated to be 0.15 billion by 2050 as global population increasing. 2) Although the pathogenesis and etiology of AD are still unknown, the hypothesis of cholinergic dysfunction and amyloid beta (Aβ) protein aggregation were made reference to be involved in the development of AD.…”

Section: Introductionmentioning

confidence: 99%

Discovery and Biological Evaluation of New Selective Acetylcholinesterase Inhibitors with Anti-Aβ Aggregation Activity through Molecular Docking-Based Virtual Screening

et al. 2020

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Discovery of novel multifunctional inhibitors targeting acetylcholinesterase (AChE) has becoming a hot spot in anti-Alzheimer's disease (AD) drug development. In the present study, four potent small molecule inhibitors (A01, A02, A03 and A04) of AChE with new chemical scaffold were identified. Inhibitor A03 displayed the most potent inhibition activity on AChE at enzymatic level with IC 50 value of 180 nM, and high selectivity towards AChE over butyrylcholinesterase (BChE) by more than 100-fold. The binding modes of compounds A01-A04 were carefully analyzed by molecular docking and molecular dynamics (MD) simulation to provide informative clues for further structure modification. Finally, the anti-amyloid beta (Aβ) aggregation and neuroprotective activity were also well investigated. Our findings highlighted the therapeutic promise of AChE inhibitors A01-A04 for AD treatment.

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“…Results from our group have demonstrated that structural modifications of the terpenoid backbone have a high impact onto the inhibitory potential for cholinesterases (ChEs) [11,12,13]. Exceptionally good ChE inhibition has been found for some amino derivatives of platanic acid [12], as well as for amides of dehydroabietylamine [14] and 12-hydroxydehydroabietylamine [15].…”

Section: Introductionmentioning

confidence: 99%

Triterpene-Based Carboxamides Act as Good Inhibitors of Butyrylcholinesterase

et al. 2019

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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.

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Novel dehydroabietylamine derivatives as potent inhibitors of acetylcholinesterase

Cited by 31 publications

References 23 publications

Bio‐based benzoxazines based on sesamol: Synthesis and properties

Bio‐based benzoxazines based on sesamol: Synthesis and properties

Discovery and Biological Evaluation of New Selective Acetylcholinesterase Inhibitors with Anti-Aβ Aggregation Activity through Molecular Docking-Based Virtual Screening

Triterpene-Based Carboxamides Act as Good Inhibitors of Butyrylcholinesterase

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