Kinetic assessment of N-methyl-2-methoxypyridinium species as phosphonate anion methylating agents

Joseph J. Topczewski; Daniel M. Quinn

doi:10.1021/ol400054m

Kinetic assessment of N-methyl-2-methoxypyridinium species as phosphonate anion methylating agents

Joseph J. Topczewski, Daniel M. Quinn

Chemistry (Twin Cities)

Research output: Contribution to journal › Article › peer-review

19 Scopus citations

Abstract

Organophosphate nerve agents and pesticides are potent inhibitors of acetylcholinesterase (AChE). Although oxime nucleophiles can reactivate the AChE-phosphyl adduct, the adduct undergoes a reaction called aging. No compounds have been described that reactivate the aged-AChE adduct. A family of 2-methoxypyridinium species which reverse aging in a model system is presented. A kinetic study of this system, which includes an SAR analysis, demonstrates that the reaction is highly tunable based on the ring substituents.

Original language	English (US)
Pages (from-to)	1084-1087
Number of pages	4
Journal	Organic Letters
Volume	15
Issue number	5
DOIs	https://doi.org/10.1021/ol400054m
State	Published - Mar 2013

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10.1021/ol400054m

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abstract = "Organophosphate nerve agents and pesticides are potent inhibitors of acetylcholinesterase (AChE). Although oxime nucleophiles can reactivate the AChE-phosphyl adduct, the adduct undergoes a reaction called aging. No compounds have been described that reactivate the aged-AChE adduct. A family of 2-methoxypyridinium species which reverse aging in a model system is presented. A kinetic study of this system, which includes an SAR analysis, demonstrates that the reaction is highly tunable based on the ring substituents.",

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AU - Quinn, Daniel M.

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AB - Organophosphate nerve agents and pesticides are potent inhibitors of acetylcholinesterase (AChE). Although oxime nucleophiles can reactivate the AChE-phosphyl adduct, the adduct undergoes a reaction called aging. No compounds have been described that reactivate the aged-AChE adduct. A family of 2-methoxypyridinium species which reverse aging in a model system is presented. A kinetic study of this system, which includes an SAR analysis, demonstrates that the reaction is highly tunable based on the ring substituents.

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Kinetic assessment of N-methyl-2-methoxypyridinium species as phosphonate anion methylating agents

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