Synthesis, molecular docking and biochemical analysis of aminoalkylated naphthalene-based chalcones as acetylcholinesterase inhibitors

Twelve novel chalcones were synthesized using 2-alkyloxy-naphthaldehydes and Mannich bases of 4-hydroxyacetophenone. The chalcones were characterized using FTIR, 1D and 2D NMR and HRMS spectroscopy. Comparative docking analysis was carried out to screen their affinity towards the AChE enzyme (PDB 1E...

Descripción completa

Guardado en:

Detalles Bibliográficos
Autores principales:	Ghadah Aljohani, Adeeb Al-Sheikh Ali, Shaya Y. Alraqa, Syazwani Itri Amran, Norazah Basar
Formato:	article
Lenguaje:	EN
Publicado:	Taylor & Francis Group 2021
Materias:	acetylcholinesterase chalcone dpph docking structure–activity relationship Science (General) Q1-390
Acceso en línea:	https://doaj.org/article/f3e653eeeede45c59bbc29d470158c16
Etiquetas:	Agregar Etiqueta Sin Etiquetas, Sea el primero en etiquetar este registro!

id	oai:doaj.org-article:f3e653eeeede45c59bbc29d470158c16
record_format	dspace
spelling	oai:doaj.org-article:f3e653eeeede45c59bbc29d470158c162021-11-26T11:19:47ZSynthesis, molecular docking and biochemical analysis of aminoalkylated naphthalene-based chalcones as acetylcholinesterase inhibitors1658-365510.1080/16583655.2021.2005921https://doaj.org/article/f3e653eeeede45c59bbc29d470158c162021-01-01T00:00:00Zhttp://dx.doi.org/10.1080/16583655.2021.2005921https://doaj.org/toc/1658-3655Twelve novel chalcones were synthesized using 2-alkyloxy-naphthaldehydes and Mannich bases of 4-hydroxyacetophenone. The chalcones were characterized using FTIR, 1D and 2D NMR and HRMS spectroscopy. Comparative docking analysis was carried out to screen their affinity towards the AChE enzyme (PDB 1EVE). All chalcones showed lower binding energy (−13.06 to −10.43 kcal/mol) against AChE better than donepezil (−10.52 kcal/mol). All chalcones were potent inhibitors towards AChE, with IC50 values ranging between 0.11 and 5.34 nM better than donepezil (IC50 33.4 nM) and selectivity indexes (0.66–23.83), despite the fact that chalcones 10 and 13 were inactive. The structure activity relationship indicated that introducing diethyl amine in ring A of the chalcone skeleton and the propargyl moiety at ring B was aﬃrmed to be a prospective drug against AChE. The multifunctional properties of chalcone 15 were all advantages that demonstrate an excellent candidate for the development of an effective drug against AChE.Ghadah AljohaniAdeeb Al-Sheikh AliShaya Y. AlraqaSyazwani Itri AmranNorazah BasarTaylor & Francis Grouparticleacetylcholinesterasechalconedpphdockingstructure–activity relationshipScience (General)Q1-390ENJournal of Taibah University for Science, Vol 15, Iss 1, Pp 781-797 (2021)
institution	DOAJ
collection	DOAJ
language	EN
topic	acetylcholinesterase chalcone dpph docking structure–activity relationship Science (General) Q1-390
spellingShingle	acetylcholinesterase chalcone dpph docking structure–activity relationship Science (General) Q1-390 Ghadah Aljohani Adeeb Al-Sheikh Ali Shaya Y. Alraqa Syazwani Itri Amran Norazah Basar Synthesis, molecular docking and biochemical analysis of aminoalkylated naphthalene-based chalcones as acetylcholinesterase inhibitors
description	Twelve novel chalcones were synthesized using 2-alkyloxy-naphthaldehydes and Mannich bases of 4-hydroxyacetophenone. The chalcones were characterized using FTIR, 1D and 2D NMR and HRMS spectroscopy. Comparative docking analysis was carried out to screen their affinity towards the AChE enzyme (PDB 1EVE). All chalcones showed lower binding energy (−13.06 to −10.43 kcal/mol) against AChE better than donepezil (−10.52 kcal/mol). All chalcones were potent inhibitors towards AChE, with IC50 values ranging between 0.11 and 5.34 nM better than donepezil (IC50 33.4 nM) and selectivity indexes (0.66–23.83), despite the fact that chalcones 10 and 13 were inactive. The structure activity relationship indicated that introducing diethyl amine in ring A of the chalcone skeleton and the propargyl moiety at ring B was aﬃrmed to be a prospective drug against AChE. The multifunctional properties of chalcone 15 were all advantages that demonstrate an excellent candidate for the development of an effective drug against AChE.
format	article
author	Ghadah Aljohani Adeeb Al-Sheikh Ali Shaya Y. Alraqa Syazwani Itri Amran Norazah Basar
author_facet	Ghadah Aljohani Adeeb Al-Sheikh Ali Shaya Y. Alraqa Syazwani Itri Amran Norazah Basar
author_sort	Ghadah Aljohani
title	Synthesis, molecular docking and biochemical analysis of aminoalkylated naphthalene-based chalcones as acetylcholinesterase inhibitors
title_short	Synthesis, molecular docking and biochemical analysis of aminoalkylated naphthalene-based chalcones as acetylcholinesterase inhibitors
title_full	Synthesis, molecular docking and biochemical analysis of aminoalkylated naphthalene-based chalcones as acetylcholinesterase inhibitors
title_fullStr	Synthesis, molecular docking and biochemical analysis of aminoalkylated naphthalene-based chalcones as acetylcholinesterase inhibitors
title_full_unstemmed	Synthesis, molecular docking and biochemical analysis of aminoalkylated naphthalene-based chalcones as acetylcholinesterase inhibitors
title_sort	synthesis, molecular docking and biochemical analysis of aminoalkylated naphthalene-based chalcones as acetylcholinesterase inhibitors
publisher	Taylor & Francis Group
publishDate	2021
url	https://doaj.org/article/f3e653eeeede45c59bbc29d470158c16
work_keys_str_mv	AT ghadahaljohani synthesismoleculardockingandbiochemicalanalysisofaminoalkylatednaphthalenebasedchalconesasacetylcholinesteraseinhibitors AT adeebalsheikhali synthesismoleculardockingandbiochemicalanalysisofaminoalkylatednaphthalenebasedchalconesasacetylcholinesteraseinhibitors AT shayayalraqa synthesismoleculardockingandbiochemicalanalysisofaminoalkylatednaphthalenebasedchalconesasacetylcholinesteraseinhibitors AT syazwaniitriamran synthesismoleculardockingandbiochemicalanalysisofaminoalkylatednaphthalenebasedchalconesasacetylcholinesteraseinhibitors AT norazahbasar synthesismoleculardockingandbiochemicalanalysisofaminoalkylatednaphthalenebasedchalconesasacetylcholinesteraseinhibitors
_version_	1718409571608821760

Synthesis, molecular docking and biochemical analysis of aminoalkylated naphthalene-based chalcones as acetylcholinesterase inhibitors

Ejemplares similares