Synthesis of New 3-Arylcoumarins Bearing N-Benzyl Triazole Moiety: Dual Lipoxygenase and Butyrylcholinesterase Inhibitors With Anti-Amyloid Aggregation and Neuroprotective Properties Against Alzheimer’S Disease

Synthesis of New 3-Arylcoumarins Bearing N-Benzyl Triazole Moiety: Dual Lipoxygenase and Butyrylcholinesterase Inhibitors With Anti-Amyloid Aggregation and Neuroprotective Properties Against Alzheimer’S Disease Publisher

Pourabdi L¹ ; Kucukkilinc TT² ; Khoshtale F¹ ; Ayazgok B² ; Nadri H³ ; Farokhi Alashti F¹ ; Forootanfar H⁴ ; Akbari T⁵ ; Shafiei M⁶ ; Foroumadi A^{6, 7} ; Sharifzadeh M⁸ ; Shafiee Ardestani M⁹ ; Abaee MS¹ ; Firoozpour L⁶ Show All Authors

Pourabdi L¹
Kucukkilinc TT²
Khoshtale F¹
Ayazgok B²
Nadri H³
Farokhi Alashti F¹
Forootanfar H⁴
Akbari T⁵
Shafiei M⁶
Foroumadi A^{6, 7}
Sharifzadeh M⁸
Shafiee Ardestani M⁹
Abaee MS¹
Firoozpour L⁶
Khoobi M^{7, 9}
Mojtahedi MM¹

Show Affiliations

1. Department of Organic Chemistry and Natural Products, Chemistry and Chemical Engineering Research Center of Iran, Tehran, Iran
2. Faculty of Pharmacy, Department of Biochemistry, Hacettepe University, Ankara, Turkey
3. Department of Medicinal Chemistry, Faculty of Pharmacy and Pharmaceutical Sciences Research Center, Shahid Sadoughi University of Medical Sciences, Yazd, Iran
4. Pharmaceutical Sciences and Cosmetic Products Research Center, Kerman University of Medical Sciences, Kerman, Iran
5. Department of Microbiology, Islamic Azad University, North Tehran Branch, Tehran, Iran
6. Department of Medicinal Chemistry, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, Iran
7. Pharmaceutical Sciences Research Center, The institute of Pharmaceutical Sciences (TIPS), Tehran University of Medical Sciences, Tehran, Iran
8. Department of Pharmacology and Toxicology, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, Iran
9. Department of Radiopharmacy, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, Iran

Source: Frontiers in Chemistry Published:2022

Abstract

A novel series of coumarin derivatives linked to the N-benzyl triazole group were synthesized and evaluated against 15-lipoxygenase (15-LOX), and acetyl- and butyrylcholinesterase (AChE and BuChE) to find the most potent derivative against Alzheimer’s disease (AD). Most of the compounds showed weak to moderate activity against ChEs. Among the most active BuChE and 15-LOX inhibitors, 8l and 8n exhibited an excellent neuroprotective effect, higher than the standard drug (quercetin) on the PC12 cell model injured by H2O2 and significantly reduced aggregation of amyloid Aβ1-42, with potencies of 1.44 and 1.79 times higher than donepezil, respectively. Compound 8l also showed more activity than butylated hydroxytoluene (BHT) as the reference antioxidant agent in reducing the levels of H2O2 activated by amyloid β in BV2 microglial cells. Kinetic and ligand–enzyme docking studies were also performed for better understanding of the mode of interaction between the best BuChE inhibitor and the enzyme. Considering the acceptable BuChE and 15-LOX inhibition activities as well as significant neuroprotection, and anti-amyloid aggregation activities, 8l and 8n could be considered as potential MTDLs for further modification and studies against AD. Copyright © 2022 Pourabdi, Kucukkilinc, Khoshtale, Ayazgok, Nadri, Farokhi Alashti, Forootanfar, Akbari, Shafiei, Foroumadi, Sharifzadeh, Shafiee Ardestani, Abaee, Firoozpour, Khoobi and Mojtahedi.

Related Docs

View other Related Docs

1. Chromone Derivatives Bearing Pyridinium Moiety As Multi-Target-Directed Ligands Against Alzheimer's Disease, Bioorganic Chemistry (2021)

2. Chromone–Lipoic Acid Conjugate: Neuroprotective Agent Having Acceptable Butyrylcholinesterase Inhibition, Antioxidant and Copper-Chelation Activities, DARU# Journal of Pharmaceutical Sciences (2021)

3. New Racemic Annulated Pyrazolo[1,2-B]Phthalazines As Tacrine-Like Ache Inhibitors With Potential Use in Alzheimer's Disease, European Journal of Medicinal Chemistry (2017)

4. Novel 3-Phenylcoumarin–Lipoic Acid Conjugates As Multi-Functional Agents for Potential Treatment of Alzheimer's Disease, Bioorganic Chemistry (2018)

5. 3-Aryl Coumarin Derivatives Bearing Aminoalkoxy Moiety As Multi-Target-Directed Ligands Against Alzheimer's Disease, Chemistry and Biodiversity (2019)

6. Coumarin Derivatives Bearing Benzoheterocycle Moiety: Synthesis, Cholinesterase Inhibitory, and Docking Simulation Study, Iranian Journal of Basic Medical Sciences (2017)

7. Anticholinesterase Activity of Cinnamic Acids Derivatives: In Vitro, in Vivo Biological Evaluation, and Docking Study, Letters in Drug Design and Discovery (2020)

8. New Classes of Carbazoles As Potential Multi-Functional Anti-Alzheimer's Agents, Bioorganic Chemistry (2019)

Experts (# of related papers)

View all Related Experts

Alireza Foroumadi (23)

Mohammad Mahdavi (23)

Style	Citing Format
MLA	Pourabdi L, et al.. "Synthesis of New 3-Arylcoumarins Bearing N-Benzyl Triazole Moiety: Dual Lipoxygenase and Butyrylcholinesterase Inhibitors With Anti-Amyloid Aggregation and Neuroprotective Properties Against Alzheimer’S Disease." Frontiers in Chemistry, vol. 9, no. , 2022, pp. -.
APA	Pourabdi L, Kucukkilinc TT, Khoshtale F, Ayazgok B, Nadri H, Farokhi Alashti F, Forootanfar H, Akbari T, Shafiei M, Foroumadi A, Sharifzadeh M, Shafiee Ardestani M, Abaee MS, Firoozpour L, Khoobi M, Mojtahedi MM (2022). Synthesis of New 3-Arylcoumarins Bearing N-Benzyl Triazole Moiety: Dual Lipoxygenase and Butyrylcholinesterase Inhibitors With Anti-Amyloid Aggregation and Neuroprotective Properties Against Alzheimer’S Disease. Frontiers in Chemistry, 9(), -.
Chicago	Pourabdi L, Kucukkilinc TT, Khoshtale F, Ayazgok B, Nadri H, Farokhi Alashti F, Forootanfar H, et al.. "Synthesis of New 3-Arylcoumarins Bearing N-Benzyl Triazole Moiety: Dual Lipoxygenase and Butyrylcholinesterase Inhibitors With Anti-Amyloid Aggregation and Neuroprotective Properties Against Alzheimer’S Disease." Frontiers in Chemistry 9, no. (2022): -.
Harvard	Pourabdi L et al. (2022) 'Synthesis of New 3-Arylcoumarins Bearing N-Benzyl Triazole Moiety: Dual Lipoxygenase and Butyrylcholinesterase Inhibitors With Anti-Amyloid Aggregation and Neuroprotective Properties Against Alzheimer’S Disease', Frontiers in Chemistry, 9(), pp. -.
Vancouver	Pourabdi L, Kucukkilinc TT, Khoshtale F, Ayazgok B, Nadri H, Farokhi Alashti F, et al.. Synthesis of New 3-Arylcoumarins Bearing N-Benzyl Triazole Moiety: Dual Lipoxygenase and Butyrylcholinesterase Inhibitors With Anti-Amyloid Aggregation and Neuroprotective Properties Against Alzheimer’S Disease. Frontiers in Chemistry. 2022;9():-.
BibTex	@article{ author = {Pourabdi L and Kucukkilinc TT and Khoshtale F and Ayazgok B and Nadri H and Farokhi Alashti F and Forootanfar H and Akbari T and Shafiei M and Foroumadi A and Sharifzadeh M and Shafiee Ardestani M and Abaee MS and Firoozpour L and Khoobi M and Mojtahedi MM}, title = {Synthesis of New 3-Arylcoumarins Bearing N-Benzyl Triazole Moiety: Dual Lipoxygenase and Butyrylcholinesterase Inhibitors With Anti-Amyloid Aggregation and Neuroprotective Properties Against Alzheimer’S Disease}, journal = {Frontiers in Chemistry}, volume = {9}, number = {}, pages = {-}, year = {2022} }
RIS	TY - JOUR AU - Pourabdi L AU - Kucukkilinc TT AU - Khoshtale F AU - Ayazgok B AU - Nadri H AU - Farokhi Alashti F AU - Forootanfar H AU - Akbari T AU - Shafiei M AU - Foroumadi A AU - Sharifzadeh M AU - Shafiee Ardestani M AU - Abaee MS AU - Firoozpour L AU - Khoobi M AU - Mojtahedi MM TI - Synthesis of New 3-Arylcoumarins Bearing N-Benzyl Triazole Moiety: Dual Lipoxygenase and Butyrylcholinesterase Inhibitors With Anti-Amyloid Aggregation and Neuroprotective Properties Against Alzheimer’S Disease JO - Frontiers in Chemistry VL - 9 IS - SP - EP - PY - 2022 ER -

Style

Citing Format

MLA

Pourabdi L, et al.. "Synthesis of New 3-Arylcoumarins Bearing N-Benzyl Triazole Moiety: Dual Lipoxygenase and Butyrylcholinesterase Inhibitors With Anti-Amyloid Aggregation and Neuroprotective Properties Against Alzheimer’S Disease." Frontiers in Chemistry, vol. 9, no. , 2022, pp. -.

APA

Pourabdi L, Kucukkilinc TT, Khoshtale F, Ayazgok B, Nadri H, Farokhi Alashti F, Forootanfar H, Akbari T, Shafiei M, Foroumadi A, Sharifzadeh M, Shafiee Ardestani M, Abaee MS, Firoozpour L, Khoobi M, Mojtahedi MM (2022). Synthesis of New 3-Arylcoumarins Bearing N-Benzyl Triazole Moiety: Dual Lipoxygenase and Butyrylcholinesterase Inhibitors With Anti-Amyloid Aggregation and Neuroprotective Properties Against Alzheimer’S Disease. Frontiers in Chemistry, 9(), -.

Chicago

Pourabdi L, Kucukkilinc TT, Khoshtale F, Ayazgok B, Nadri H, Farokhi Alashti F, Forootanfar H, et al.. "Synthesis of New 3-Arylcoumarins Bearing N-Benzyl Triazole Moiety: Dual Lipoxygenase and Butyrylcholinesterase Inhibitors With Anti-Amyloid Aggregation and Neuroprotective Properties Against Alzheimer’S Disease." Frontiers in Chemistry 9, no. (2022): -.

Harvard

Pourabdi L et al. (2022) 'Synthesis of New 3-Arylcoumarins Bearing N-Benzyl Triazole Moiety: Dual Lipoxygenase and Butyrylcholinesterase Inhibitors With Anti-Amyloid Aggregation and Neuroprotective Properties Against Alzheimer’S Disease', Frontiers in Chemistry, 9(), pp. -.

Vancouver

Pourabdi L, Kucukkilinc TT, Khoshtale F, Ayazgok B, Nadri H, Farokhi Alashti F, et al.. Synthesis of New 3-Arylcoumarins Bearing N-Benzyl Triazole Moiety: Dual Lipoxygenase and Butyrylcholinesterase Inhibitors With Anti-Amyloid Aggregation and Neuroprotective Properties Against Alzheimer’S Disease. Frontiers in Chemistry. 2022;9():-.

BibTex

@article{ author = {Pourabdi L and Kucukkilinc TT and Khoshtale F and Ayazgok B and Nadri H and Farokhi Alashti F and Forootanfar H and Akbari T and Shafiei M and Foroumadi A and Sharifzadeh M and Shafiee Ardestani M and Abaee MS and Firoozpour L and Khoobi M and Mojtahedi MM}, title = {Synthesis of New 3-Arylcoumarins Bearing N-Benzyl Triazole Moiety: Dual Lipoxygenase and Butyrylcholinesterase Inhibitors With Anti-Amyloid Aggregation and Neuroprotective Properties Against Alzheimer’S Disease}, journal = {Frontiers in Chemistry}, volume = {9}, number = {}, pages = {-}, year = {2022} }

RIS

TY - JOUR
AU - Pourabdi L
AU - Kucukkilinc TT
AU - Khoshtale F
AU - Ayazgok B
AU - Nadri H
AU - Farokhi Alashti F
AU - Forootanfar H
AU - Akbari T
AU - Shafiei M
AU - Foroumadi A
AU - Sharifzadeh M
AU - Shafiee Ardestani M
AU - Abaee MS
AU - Firoozpour L
AU - Khoobi M
AU - Mojtahedi MM
TI - Synthesis of New 3-Arylcoumarins Bearing N-Benzyl Triazole Moiety: Dual Lipoxygenase and Butyrylcholinesterase Inhibitors With Anti-Amyloid Aggregation and Neuroprotective Properties Against Alzheimer’S Disease
JO - Frontiers in Chemistry
VL - 9
IS -
SP -
EP -
PY - 2022
ER -

Science Communicator Platform

Authors

Authors Affiliations

Abstract