Phenethyl Esters and Amide of Ferulic Acid, Hydroferulic Acid, Homovanillic Acid, and Vanillic Acid: Synthesis, Free Radicals Scavenging Activity, and Molecular Modeling as Potential Cholinesterases Inhibitors
As ferulic acid was reported to be involved in novel potential mechanisms associated with Alzheimer’s disease (AD) therapy, five closely related phenethyl esters and amide of this natural product were synthesized and screened for their free radicals scavenging activity. Ferulic acid and its analogue...
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MDPI AG
2020-08-01
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| Online Access: | https://www.mdpi.com/1422-8599/2020/3/M1151 |
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| author | Ayyoub Selka Fanta J. Ndongou Moutombi Marc Cormier Mohamed Touaibia |
| author_facet | Ayyoub Selka Fanta J. Ndongou Moutombi Marc Cormier Mohamed Touaibia |
| author_sort | Ayyoub Selka |
| collection | DOAJ |
| description | As ferulic acid was reported to be involved in novel potential mechanisms associated with Alzheimer’s disease (AD) therapy, five closely related phenethyl esters and amide of this natural product were synthesized and screened for their free radicals scavenging activity. Ferulic acid and its analogue′s absorption, distribution, metabolism, and excretion (ADME) properties were predicted. All compounds obey Lipinski′s rules. Moreover, all evaluated compounds seem to present a high oral bioavailability and blood–brain barrier (BBB) permeation which is crucial for Alzheimer′s disease drug candidates. Molecular docking of analogues <b>4</b> and <b>8</b> with acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) showed interactions with the residues of the catalytic triad of AChE and BChE. In addition to their interactions with the anionic subsite, hydroferulic acid phenethyl ester <b>4</b> and homovanillic acid phenethyl ester <b>8</b> may have potential as inhibitors of AChE and BChE, respectively. |
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| institution | Directory Open Access Journal |
| issn | 1422-8599 |
| language | English |
| last_indexed | 2024-03-10T17:43:55Z |
| publishDate | 2020-08-01 |
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| record_format | Article |
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| spelling | doaj.art-87c3293a6ca248fc8c9093486119a8f82023-11-20T09:35:59ZengMDPI AGMolbank1422-85992020-08-0120203M115110.3390/M1151Phenethyl Esters and Amide of Ferulic Acid, Hydroferulic Acid, Homovanillic Acid, and Vanillic Acid: Synthesis, Free Radicals Scavenging Activity, and Molecular Modeling as Potential Cholinesterases InhibitorsAyyoub Selka0Fanta J. Ndongou Moutombi1Marc Cormier2Mohamed Touaibia3Department of Chemistry and Biochemistry, Université de Moncton, Moncton, NB E1A 3E9, CanadaDepartment of Chemistry and Biochemistry, Université de Moncton, Moncton, NB E1A 3E9, CanadaDepartment of Chemistry and Biochemistry, Université de Moncton, Moncton, NB E1A 3E9, CanadaDepartment of Chemistry and Biochemistry, Université de Moncton, Moncton, NB E1A 3E9, CanadaAs ferulic acid was reported to be involved in novel potential mechanisms associated with Alzheimer’s disease (AD) therapy, five closely related phenethyl esters and amide of this natural product were synthesized and screened for their free radicals scavenging activity. Ferulic acid and its analogue′s absorption, distribution, metabolism, and excretion (ADME) properties were predicted. All compounds obey Lipinski′s rules. Moreover, all evaluated compounds seem to present a high oral bioavailability and blood–brain barrier (BBB) permeation which is crucial for Alzheimer′s disease drug candidates. Molecular docking of analogues <b>4</b> and <b>8</b> with acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) showed interactions with the residues of the catalytic triad of AChE and BChE. In addition to their interactions with the anionic subsite, hydroferulic acid phenethyl ester <b>4</b> and homovanillic acid phenethyl ester <b>8</b> may have potential as inhibitors of AChE and BChE, respectively.https://www.mdpi.com/1422-8599/2020/3/M1151ferulic acidphenethyl estersAlzheimer’s diseasecholinesterasesradicals scavengingmolecular docking |
| spellingShingle | Ayyoub Selka Fanta J. Ndongou Moutombi Marc Cormier Mohamed Touaibia Phenethyl Esters and Amide of Ferulic Acid, Hydroferulic Acid, Homovanillic Acid, and Vanillic Acid: Synthesis, Free Radicals Scavenging Activity, and Molecular Modeling as Potential Cholinesterases Inhibitors Molbank ferulic acid phenethyl esters Alzheimer’s disease cholinesterases radicals scavenging molecular docking |
| title | Phenethyl Esters and Amide of Ferulic Acid, Hydroferulic Acid, Homovanillic Acid, and Vanillic Acid: Synthesis, Free Radicals Scavenging Activity, and Molecular Modeling as Potential Cholinesterases Inhibitors |
| title_full | Phenethyl Esters and Amide of Ferulic Acid, Hydroferulic Acid, Homovanillic Acid, and Vanillic Acid: Synthesis, Free Radicals Scavenging Activity, and Molecular Modeling as Potential Cholinesterases Inhibitors |
| title_fullStr | Phenethyl Esters and Amide of Ferulic Acid, Hydroferulic Acid, Homovanillic Acid, and Vanillic Acid: Synthesis, Free Radicals Scavenging Activity, and Molecular Modeling as Potential Cholinesterases Inhibitors |
| title_full_unstemmed | Phenethyl Esters and Amide of Ferulic Acid, Hydroferulic Acid, Homovanillic Acid, and Vanillic Acid: Synthesis, Free Radicals Scavenging Activity, and Molecular Modeling as Potential Cholinesterases Inhibitors |
| title_short | Phenethyl Esters and Amide of Ferulic Acid, Hydroferulic Acid, Homovanillic Acid, and Vanillic Acid: Synthesis, Free Radicals Scavenging Activity, and Molecular Modeling as Potential Cholinesterases Inhibitors |
| title_sort | phenethyl esters and amide of ferulic acid hydroferulic acid homovanillic acid and vanillic acid synthesis free radicals scavenging activity and molecular modeling as potential cholinesterases inhibitors |
| topic | ferulic acid phenethyl esters Alzheimer’s disease cholinesterases radicals scavenging molecular docking |
| url | https://www.mdpi.com/1422-8599/2020/3/M1151 |
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