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Design and Synthesis of Novel Anti-Alzheimer's Agents: Acridine-Chromenone and Quinoline-Chromenone Hybrids Publisher Pubmed



Najafi Z1 ; Saeedi M2, 3 ; Mahdavi M4 ; Sabourian R3 ; Khanavi M5 ; Tehrani MB1 ; Moghadam FH6 ; Edraki N7 ; Karimporrazkenari E3 ; Sharifzadeh M8 ; Foroumadi A9 ; Shafiee A9 ; Akbarzadeh T1, 3
Authors
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Authors Affiliations
  1. 1. Department of Medicinal Chemistry, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, Iran
  2. 2. Medicinal Plants Research Center, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, Iran
  3. 3. Persian Medicine and Pharmacy Research Center, Tehran University of Medical Sciences, Tehran, Iran
  4. 4. Drug Design and Development Research Center, Tehran University of Medical Sciences, Tehran, Iran
  5. 5. Department of Pharmacognosy, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, Iran
  6. 6. Department of Cellular Biotechnology at Cell Science Research Center, Royan Institute for Biotechnology, ACECR, Isfahan, Iran
  7. 7. Medicinal and Natural Products Chemistry Research Center, Shiraz University of Medical Sciences, Shiraz, Iran
  8. 8. Department of Pharmacology and Toxicology, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, Iran
  9. 9. Department of Medicinal Chemistry, Faculty of Pharmacy and Pharmaceutical Sciences Research Center, Tehran University of Medical Sciences, Tehran, Iran

Source: Bioorganic Chemistry Published:2016


Abstract

A novel series of acridine-chromenone and quinoline-chromenone hybrids were designed, synthesized, and evaluated as anti-Alzheimer's agents. All synthesized compounds were evaluated as cholinesterases (ChEs) inhibitors and among them, 7-(4-(6-chloro-2,3-dihydro-1H-cyclopenta[b]quinolin-9-ylamino)phenoxy)-4-methyl-2H-chromen-2-one (8e) exhibited the most potent anti-acetylcholinesterase (AChE) inhibitory activity (IC50 = 16.17 μM) comparing with rivastigmine (IC50 = 11.07 μM) as the reference drug. Also, compound 8e was assessed for its β-secretase (BACE1) inhibitory and neuroprotective activities which demonstrated satisfactory results. It should be noted that both kinetic study on the inhibition of AChE and molecular modeling revealed that compound 8e interacted simultaneously with both the catalytic active site (CAS) and peripheral anionic site (PAS) of AChE. © 2016 Elsevier Inc.
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