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Design, synthesis, molecular modeling and anticholinesterase activity of benzylidene-benzofuran-3-ones containing cyclic amine side chain

    Farzad Mehrabi

    Department of Neuroscience, Faculty of Medicine, AJA University of Medical Sciences, Tehran, Iran

    ,
    Yaghoub Pourshojaei

    Department of Medicinal Chemistry, Faculty of Pharmacy & Pharmaceutics Research Center, Institute of Neuropharmacology, Kerman University of Medical Sciences, Kerman, Iran

    Department of Neuroscience, Neuroscience Research Center, Institute of Neuropharmacology, Kerman University of Medical Sciences, Kerman, Iran

    ,
    Alireza Moradi

    Department of Medicinal Chemistry, Faculty of Pharmacy, Shahid Sadoughi University of Medical Sciences, Yazd, Iran

    ,
    Mohammad Sharifzadeh

    Department of Toxicology & Pharmacology, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, Iran

    ,
    Leila Khosravani

    Department of Medicinal Chemistry, Drug Design & Development Research Center, Tehran University of Medical Sciences, Tehran, Iran

    ,
    Reyhaneh Sabourian

    Department of Medicinal Chemistry, Drug Design & Development Research Center, Tehran University of Medical Sciences, Tehran, Iran

    ,
    Samira Rahmani-Nezhad

    Department of Medicinal Chemistry, Faculty of Pharmacy & Pharmaceutical Sciences Research Center, Tehran University of Medical Sciences, Tehran, Iran

    ,
    Maryam Mohammadi-Khanaposhtani

    Department of Medicinal Chemistry, Faculty of Pharmacy & Pharmaceutical Sciences Research Center, Tehran University of Medical Sciences, Tehran, Iran

    ,
    Mohammad Mahdavi

    Department of Medicinal Chemistry, Drug Design & Development Research Center, Tehran University of Medical Sciences, Tehran, Iran

    ,
    Ali Asadipour

    Department of Medicinal Chemistry, Faculty of Pharmacy & Pharmaceutics Research Center, Institute of Neuropharmacology, Kerman University of Medical Sciences, Kerman, Iran

    ,
    Hamid Reza Rahimi

    Department of Toxicology & Pharmacology, Faculty of Pharmacy, Kerman University of Medical Sciences, Kerman, Iran

    ,
    Setareh Moghimi

    Department of Medicinal Chemistry, Drug Design & Development Research Center, Tehran University of Medical Sciences, Tehran, Iran

    &
    Alireza Foroumadi

    *Author for correspondence:

    E-mail Address: aforoumadi@yahoo.com

    Department of Medicinal Chemistry, Drug Design & Development Research Center, Tehran University of Medical Sciences, Tehran, Iran

    Department of Medicinal Chemistry, Faculty of Pharmacy & Pharmaceutical Sciences Research Center, Tehran University of Medical Sciences, Tehran, Iran

    Published Online:https://doi.org/10.4155/fmc-2016-0237

    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.

    Papers of special note have been highlighted as: • of interest; •• of considerable interest

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