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Paper | Regular issue | Vol 71, No. 11, 2007, pp.2413-2425
Published online, 8th August, 2007
DOI: 10.3987/COM-07-11136
Syntheses and Anticholinesterase Activities of Novel 3-Aminocarbonylmethylene-3-methyl-2,3-dihydrobenzofuran-5-yl Carbamates

Weiming Luo, Qian-sheng Yu, Harold W. Holloway, David Tweedie, Damon Parrish, Arnold Brossi, and Nigel H. Greig*

*Drug Design & Development Section, Laboratory of Neurosciences, Intramural Research Program, National Institute on Aging, National Institutes of Health, 5600 Nathan Shock Drive, Baltimore, Maryland 21224, U.S.A.

Abstract

Novel carbamates 4 and 5 were synthesized from starting material 5-hydroxy-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.