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



Mehrabi F¹ ; Pourshojaei Y^{2, 3} ; Moradi A⁴ ; Sharifzadeh M⁵ ; Khosravani L⁶ ; Sabourian R⁶ ; Rahmaninezhad S⁷ ; Mohammadikhanaposhtani M⁷ ; Mahdavi M⁶ ; Asadipour A² ; Rahimi HR⁸ ; Moghimi S⁶ ; Foroumadi A^{6, 7}
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.