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Design, Synthesis, Molecular Modeling and Anticholinesterase Activity of Benzylidene-Benzofuran-3-Ones Containing Cyclic Amine Side Chain Publisher Pubmed



Mehrabi F1 ; Pourshojaei Y2, 3 ; Moradi A4 ; Sharifzadeh M5 ; Khosravani L6 ; Sabourian R6 ; Rahmaninezhad S7 ; Mohammadikhanaposhtani M7 ; Mahdavi M6 ; Asadipour A2 ; Rahimi HR8 ; Moghimi S6 ; Foroumadi A6, 7
Authors
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Authors Affiliations
  1. 1. Department of Neuroscience, Faculty of Medicine, AJA University of Medical Sciences, Tehran, Iran
  2. 2. Department of Medicinal Chemistry, Faculty of Pharmacy and Pharmaceutics Research Center, Institute of Neuropharmacology, Kerman University of Medical Sciences, Kerman, Iran
  3. 3. Department of Neuroscience, Neuroscience Research Center, Institute of Neuropharmacology, Kerman University of Medical Sciences, Kerman, Iran
  4. 4. Department of Medicinal Chemistry, Faculty of Pharmacy, Shahid Sadoughi University of Medical Sciences, Yazd, Iran
  5. 5. Department of Toxicology and Pharmacology, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, Iran
  6. 6. Department of Medicinal Chemistry, Drug Design and Development Research Center, Tehran University of Medical Sciences, Tehran, Iran
  7. 7. Department of Medicinal Chemistry, Faculty of Pharmacy and Pharmaceutical Sciences Research Center, Tehran University of Medical Sciences, Tehran, Iran
  8. 8. Department of Toxicology and Pharmacology, Faculty of Pharmacy, Kerman University of Medical Sciences, Kerman, Iran

Source: Future Medicinal Chemistry Published:2017


Abstract

Aim: A series of 2-benzylidene-benzofuran-3-ones were designed from the structures of Ebselen analogs and aurone derivatives and synthesized in good yields. Materials & methods: The target compounds were prepared by the condensation reaction between appropriate benzofuranones with amino alkoxy aldehydes and evaluated as cholinesterase inhibitors by Ellman's method. Results: The in vitro anti-acetylcholinesterase (AChE)/butyrylcholinesterase activities of the synthesized compounds revealed that 7e (IC50 = 0.045 μM) is the most active compound against AChE. Furthermore, the docking study confirmed the results obtained through in vitro experiments and predicted the possible binding conformation. Conclusion: The anticholinesterase activities of benzylidene-benzofurane-3-ones as aurone analogs revealed that the compounds bearing piperidinylethoxy residue showed better activities against AChE, introducing these compounds for further drug discovery developments.
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