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3-Aryl Coumarin Derivatives Bearing Aminoalkoxy Moiety As Multi-Target-Directed Ligands Against Alzheimer's Disease Publisher Pubmed



Abdshahzadeh H1 ; Golshani M2 ; Nadri H3 ; Saberi Kia I2 ; Abdolahi Z3 ; Forootanfar H4 ; Ameri A5 ; Tuylu Kucukkilinc T6 ; Ayazgok B6 ; Jalilibaleh L2 ; Sadat Ebrahimi SE1 ; Moghimi S2 ; Haririan I7, 8 ; Khoobi M2, 9 Show All Authors
Authors
  1. Abdshahzadeh H1
  2. Golshani M2
  3. Nadri H3
  4. Saberi Kia I2
  5. Abdolahi Z3
  6. Forootanfar H4
  7. Ameri A5
  8. Tuylu Kucukkilinc T6
  9. Ayazgok B6
  10. Jalilibaleh L2
  11. Sadat Ebrahimi SE1
  12. Moghimi S2
  13. Haririan I7, 8
  14. Khoobi M2, 9
  15. Foroumadi A1, 10
Show Affiliations
Authors Affiliations
  1. 1. Department of Medicinal Chemistry, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, 14176, Iran
  2. 2. The Institute of Pharmaceutical Sciences (TIPS), Tehran University of Medical Sciences, Tehran, 14176, Iran
  3. 3. Faculty of Pharmacy and Pharmaceutical Sciences Research Center, Shahid Sadoughi University of Medical Sciences, Yazd, 37240171-035, Iran
  4. 4. Pharmaceutics Research Center, Institute of Neuropharmacology, Kerman, University of Medical Sciences, Kerman, 7616913555, Iran
  5. 5. Department of Medicinal Chemistry, Faculty of Pharmacy, Kerman University of Medical Sciences, Kerman, 7616913555, Iran
  6. 6. Hacettepe University, Faculty of Pharmacy, Department of Biochemistry, Ankara, 06100, Turkey
  7. 7. Biosensor Research Center, Endocrinology and Metabolism Molecular-Cellular Sciences Institute, Tehran University of Medical Sciences, Tehran, 1416753955, Iran
  8. 8. Center of Excellence in Electrochemistry, Faculty of Chemistry, University of Tehran, Tehran, Iran
  9. 9. Department of Pharmaceutical Biomaterials and Medical Biomaterials Research Center, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, 1416753955, Iran
  10. 10. Neuroscience Research Center, Institute of Neuropharmacology, Kerman University of Medical Sciences, Kerman, 7616913555, Iran

Source: Chemistry and Biodiversity Published:2019


Abstract

Two series of novel coumarin derivatives, substituted at 3 and 7 positions with aminoalkoxy groups, are synthesized, characterized, and screened. The effect of amine substituents and the length of cross-linker are investigated in acetyl- and butyrylcholinesterase (AChE and BuChE) inhibition. Target compounds show moderate to potent inhibitory activities against AChE and BuChE. 3-(3,4-Dichlorophenyl)-7-[4-(diethylamino)butoxy]-2H-chromen-2-one (4y) is identified as the most potent compound against AChE (IC50=0.27 μm). Kinetic and molecular modeling studies affirmed that compound 4y works in a mixed-type way and interacts simultaneously with the catalytic active site (CAS) and peripheral anionic site (PAS) of AChE. In addition, compound 4y blocks β-amyloid (Aβ) self-aggregation with a ratio of 44.11 % at 100 μm and significantly protects PC12 cells from H2O2-damage in a dose-dependent manner. © 2019 Wiley-VHCA AG, Zurich, Switzerland
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