Synthesis, docking study, and biological evaluation of novel umbellipherone/hymecromone derivatives as acetylcholinesterase/butyrylcholinesterase inhibitors

Synthesis, docking study, and biological evaluation of novel umbellipherone/hymecromone... A novel hybrid series of umbellipherone and benzyl amine scaffolds, linked via triazole ring, was synthesized and evaluated as both acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) inhibitors. Most of the synthesized compounds showed moderate to high activities by using Ellman’s modified assay. Among the target compounds, 6e bearing 3-methoxy substituent on benzyl moiety was the most active one (AChE and BuChE IC = 3.4 and 1.1 μM, respectively). Finally, binding modes of the target compound was studied using molecular docking stimulations. The neuroprotectivity evaluation exhibited that this compound efficiently protected PC12 neurons against H O -induced cell death. 2 2 ● ● ● Keywords Alzheimer’s disease Cholinesterase inhibitor Docking Umbellipherone derivatives Introduction Electronic supplementary material The online version of this article Alzheimer’s disease (AD) is known as the frequent type of (https://doi.org/10.1007/s00044-018-2187-8) contains supplementary material, which is available to authorized users. dementia among older adults. The related symptoms include loss of memory, decrease in cognitive function and beha- * Mehdi Khoobi vioral impairment affecting on many lives worldwide khoobi@tums.ac.ir (Palmer 2011). The exact reason of Alzheimer’s disease is Alireza Foroumadi poorly understood, but there are some identified causes, aforoumadi@yahoo.com explaining the pathology of AD, including decline in acet- Department of http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Medicinal Chemistry Research Springer Journals

Synthesis, docking study, and biological evaluation of novel umbellipherone/hymecromone derivatives as acetylcholinesterase/butyrylcholinesterase inhibitors

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Publisher
Springer US
Copyright
Copyright © 2018 by Springer Science+Business Media, LLC, part of Springer Nature
Subject
Biomedicine; Pharmacology/Toxicology; Biochemistry, general; Cell Biology
ISSN
1054-2523
eISSN
1554-8120
D.O.I.
10.1007/s00044-018-2187-8
Publisher site
See Article on Publisher Site

Abstract

A novel hybrid series of umbellipherone and benzyl amine scaffolds, linked via triazole ring, was synthesized and evaluated as both acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) inhibitors. Most of the synthesized compounds showed moderate to high activities by using Ellman’s modified assay. Among the target compounds, 6e bearing 3-methoxy substituent on benzyl moiety was the most active one (AChE and BuChE IC = 3.4 and 1.1 μM, respectively). Finally, binding modes of the target compound was studied using molecular docking stimulations. The neuroprotectivity evaluation exhibited that this compound efficiently protected PC12 neurons against H O -induced cell death. 2 2 ● ● ● Keywords Alzheimer’s disease Cholinesterase inhibitor Docking Umbellipherone derivatives Introduction Electronic supplementary material The online version of this article Alzheimer’s disease (AD) is known as the frequent type of (https://doi.org/10.1007/s00044-018-2187-8) contains supplementary material, which is available to authorized users. dementia among older adults. The related symptoms include loss of memory, decrease in cognitive function and beha- * Mehdi Khoobi vioral impairment affecting on many lives worldwide khoobi@tums.ac.ir (Palmer 2011). The exact reason of Alzheimer’s disease is Alireza Foroumadi poorly understood, but there are some identified causes, aforoumadi@yahoo.com explaining the pathology of AD, including decline in acet- Department of

Journal

Medicinal Chemistry ResearchSpringer Journals

Published: May 30, 2018

References

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