Synthesis and characterization of new chalcone derivatives as acetylcholinesterase inhibitor

Synthesis and characterization of new chalcone derivatives as acetylcholinesterase inhibitor

Chalcones are open-chain flavonoids and considered to be precursors of isoflavonoids and flavonoids which consist of two aromatic rings that linked by a three carbon consist of a, ß-unsaturated carbonyl system. Besides, chalcones display a wide range of biological activities such as antibacterial, a...

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Main Author: Ali, Arman Abdalla
Format: Thesis
Language:English
Published: 2020
Subjects:
QD Chemistry
Online Access:http://eprints.utm.my/id/eprint/102053/1/ArmanAbdallaAliMFS2020.pdf
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id my-utm-ep.102053
record_format uketd_dc
institution Universiti Teknologi Malaysia
collection UTM Institutional Repository
language English
topic QD Chemistry
spellingShingle QD Chemistry
Ali, Arman Abdalla
Synthesis and characterization of new chalcone derivatives as acetylcholinesterase inhibitor
description Chalcones are open-chain flavonoids and considered to be precursors of isoflavonoids and flavonoids which consist of two aromatic rings that linked by a three carbon consist of a, ß-unsaturated carbonyl system. Besides, chalcones display a wide range of biological activities such as antibacterial, anticancer, antioxidant including AChE inhibition activities. Super-activation of cholinesterase (acetylcholinesterase) is linked to various neurological problems most precisely Alzheimer’s disease (AD), which leads to senile dementia. Therefore, cholinesterase (AChE) inhibition is considered as a promising strategy for the treatment of Alzheimer’s disease. For this purpose, this study focused on the synthesis of a series of new chalcone derivatives with anti-cholinesterase potential. In the first step of this study 1-(4-(benzyloxy)phenyl)ethan-1-one (51) was successfully synthesized by benzylation of 4-hydroxy acetophenone with a yield of 88.49% as a precursor to synthesize a series of chalcone derivatives. Then, the precursor was reacted with benzaldehyde derivatives (52a-f) with different substituent groups on its para position (4-H, 4-Br, 4-NO2, 4-isopropyl, 4-OCH3, and 4-Cl), respectively, by base-catalyzed Claisen-Schmidt condensation reaction to produce a series of new chalcone derivatives (53a-f). The yield of synthesized compounds were (50-58%), and their molecular structures were confirmed using IR, 1H NMR and 13C NMR analysis. The synthesized chalcone derivatives (53a-f) were tested against AChE. All compounds showed good activity in AChE inhibition. Moreover, compounds with the presence of electron-withdrawing groups (53b, 53c and 53f) showed excellent activity in AChE inhibition, Among them, compound (53c) showed the most potent activity (89.44%) in acetylcholinesterase inhibition which quite near from the result of the standard Galantamine (94.11%).Chalcones are open-chain flavonoids and considered to be precursors of isoflavonoids and flavonoids which consist of two aromatic rings that linked by a three carbon consist of a, ß-unsaturated carbonyl system. Besides, chalcones display a wide range of biological activities such as antibacterial, anticancer, antioxidant including AChE inhibition activities. Super-activation of cholinesterase (acetylcholinesterase) is linked to various neurological problems most precisely Alzheimer’s disease (AD), which leads to senile dementia. Therefore, cholinesterase (AChE) inhibition is considered as a promising strategy for the treatment of Alzheimer’s disease. For this purpose, this study focused on the synthesis of a series of new chalcone derivatives with anti-cholinesterase potential. In the first step of this study 1-(4-(benzyloxy)phenyl)ethan-1-one (51) was successfully synthesized by benzylation of 4-hydroxy acetophenone with a yield of 88.49% as a precursor to synthesize a series of chalcone derivatives. Then, the precursor was reacted with benzaldehyde derivatives (52a-f) with different substituent groups on its para position (4-H, 4-Br, 4-NO2, 4-isopropyl, 4-OCH3, and 4-Cl), respectively, by base-catalyzed Claisen-Schmidt condensation reaction to produce a series of new chalcone derivatives (53a-f). The yield of synthesized compounds were (50-58%), and their molecular structures were confirmed using IR, 1H NMR and 13C NMR analysis. The synthesized chalcone derivatives (53a-f) were tested against AChE. All compounds showed good activity in AChE inhibition. Moreover, compounds with the presence of electron-withdrawing groups (53b, 53c and 53f) showed excellent activity in AChE inhibition, Among them, compound (53c) showed the most potent activity (89.44%) in acetylcholinesterase inhibition which quite near from the result of the standard Galantamine (94.11%).
format Thesis
qualification_level Master's degree
author Ali, Arman Abdalla
author_facet Ali, Arman Abdalla
author_sort Ali, Arman Abdalla
title Synthesis and characterization of new chalcone derivatives as acetylcholinesterase inhibitor
title_short Synthesis and characterization of new chalcone derivatives as acetylcholinesterase inhibitor
title_full Synthesis and characterization of new chalcone derivatives as acetylcholinesterase inhibitor
title_fullStr Synthesis and characterization of new chalcone derivatives as acetylcholinesterase inhibitor
title_full_unstemmed Synthesis and characterization of new chalcone derivatives as acetylcholinesterase inhibitor
title_sort synthesis and characterization of new chalcone derivatives as acetylcholinesterase inhibitor
granting_institution Universiti Teknologi Malaysia, Faculty of Science
granting_department Faculty of Science
publishDate 2020
url http://eprints.utm.my/id/eprint/102053/1/ArmanAbdallaAliMFS2020.pdf
_version_ 1776100834772254720
spelling my-utm-ep.1020532023-07-31T07:30:17Z Synthesis and characterization of new chalcone derivatives as acetylcholinesterase inhibitor 2020 Ali, Arman Abdalla QD Chemistry Chalcones are open-chain flavonoids and considered to be precursors of isoflavonoids and flavonoids which consist of two aromatic rings that linked by a three carbon consist of a, ß-unsaturated carbonyl system. Besides, chalcones display a wide range of biological activities such as antibacterial, anticancer, antioxidant including AChE inhibition activities. Super-activation of cholinesterase (acetylcholinesterase) is linked to various neurological problems most precisely Alzheimer’s disease (AD), which leads to senile dementia. Therefore, cholinesterase (AChE) inhibition is considered as a promising strategy for the treatment of Alzheimer’s disease. For this purpose, this study focused on the synthesis of a series of new chalcone derivatives with anti-cholinesterase potential. In the first step of this study 1-(4-(benzyloxy)phenyl)ethan-1-one (51) was successfully synthesized by benzylation of 4-hydroxy acetophenone with a yield of 88.49% as a precursor to synthesize a series of chalcone derivatives. Then, the precursor was reacted with benzaldehyde derivatives (52a-f) with different substituent groups on its para position (4-H, 4-Br, 4-NO2, 4-isopropyl, 4-OCH3, and 4-Cl), respectively, by base-catalyzed Claisen-Schmidt condensation reaction to produce a series of new chalcone derivatives (53a-f). The yield of synthesized compounds were (50-58%), and their molecular structures were confirmed using IR, 1H NMR and 13C NMR analysis. The synthesized chalcone derivatives (53a-f) were tested against AChE. All compounds showed good activity in AChE inhibition. Moreover, compounds with the presence of electron-withdrawing groups (53b, 53c and 53f) showed excellent activity in AChE inhibition, Among them, compound (53c) showed the most potent activity (89.44%) in acetylcholinesterase inhibition which quite near from the result of the standard Galantamine (94.11%).Chalcones are open-chain flavonoids and considered to be precursors of isoflavonoids and flavonoids which consist of two aromatic rings that linked by a three carbon consist of a, ß-unsaturated carbonyl system. Besides, chalcones display a wide range of biological activities such as antibacterial, anticancer, antioxidant including AChE inhibition activities. Super-activation of cholinesterase (acetylcholinesterase) is linked to various neurological problems most precisely Alzheimer’s disease (AD), which leads to senile dementia. Therefore, cholinesterase (AChE) inhibition is considered as a promising strategy for the treatment of Alzheimer’s disease. For this purpose, this study focused on the synthesis of a series of new chalcone derivatives with anti-cholinesterase potential. In the first step of this study 1-(4-(benzyloxy)phenyl)ethan-1-one (51) was successfully synthesized by benzylation of 4-hydroxy acetophenone with a yield of 88.49% as a precursor to synthesize a series of chalcone derivatives. Then, the precursor was reacted with benzaldehyde derivatives (52a-f) with different substituent groups on its para position (4-H, 4-Br, 4-NO2, 4-isopropyl, 4-OCH3, and 4-Cl), respectively, by base-catalyzed Claisen-Schmidt condensation reaction to produce a series of new chalcone derivatives (53a-f). The yield of synthesized compounds were (50-58%), and their molecular structures were confirmed using IR, 1H NMR and 13C NMR analysis. The synthesized chalcone derivatives (53a-f) were tested against AChE. All compounds showed good activity in AChE inhibition. Moreover, compounds with the presence of electron-withdrawing groups (53b, 53c and 53f) showed excellent activity in AChE inhibition, Among them, compound (53c) showed the most potent activity (89.44%) in acetylcholinesterase inhibition which quite near from the result of the standard Galantamine (94.11%). 2020 Thesis http://eprints.utm.my/id/eprint/102053/ http://eprints.utm.my/id/eprint/102053/1/ArmanAbdallaAliMFS2020.pdf application/pdf en public http://dms.library.utm.my:8080/vital/access/manager/Repository/vital:146250 masters Universiti Teknologi Malaysia, Faculty of Science Faculty of Science

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