Synthesis of organophosphates with fluorine-containing leaving groups as serine esterase inhibitors with potential for Alzheimer disease therapeutics

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Abstract

Acetylcholinesterase and butyrylcholinesterase inhibitors are potential cognition enhancers in Alzheimer disease. O,O-Dialkylphosphate inhibitors with 1-substituted 2,2,2-trifluoroethoxy leaving groups were synthesized by phosphonate-phosphate rearrangement. Substituents in the 1-position of the leaving group along with the O-alkyl groups modulated potency and selectivity against acetylcholinesterase, butyrylcholinesterase, and carboxylesterase. © 2009 Elsevier Ltd. All rights reserved.

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Makhaeva, G. F., Aksinenko, A. Y., Sokolov, V. B., Serebryakova, O. G., & Richardson, R. J. (2009). Synthesis of organophosphates with fluorine-containing leaving groups as serine esterase inhibitors with potential for Alzheimer disease therapeutics. Bioorganic and Medicinal Chemistry Letters, 19(19), 5528–5530. https://doi.org/10.1016/j.bmcl.2009.08.065

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