Syntheses and Anticholinesterase Activities of Novel 3-Aminocarbonylmethylene-3-methyl-2,3-dihydrobenzofuran-5-yl Carbamates

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Novel carbamates 4 and 5 were synthesized from starting material 5hydroxy-3-methyl-3H-benzofuran-2-one, 17.The acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibitory activities of 4 and 5 were determined against fresh human enzyme, are in the realm of clinically valuable compounds and are discussed.In addition, the reductive properties of the 2-carbonyl group of 3H-benzofuran-2-one, possessing an unsaturated substituted group in its 3 position (9, 11 and 14), were studied.Carbamates based on physostigmine series 1a-1c, on physovenine series 2a-2c and on tetrahydrofurobenzofuran series 3a-3c have been proven to be potent inhibitors of the enzymes acetylcholinesterase (AChE) or butyrylcholinesterase (BChE), with specific compounds exhibiting remarkable selectivity for one form of the enzyme over the other.These enzymes are validated targets in the treatment of Alzheimer's disease (AD), and their characterization is leading to the development of new and better tolerated drug candidates with actions that may impact disease course.][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17] Herein, we report the chemical synthesis and anticholinesterase properties of the novel and unexpected carbamates, 4 and 5.