Journal of medicinal chemistry

Sulfur derivatives of 2-oxopropanal oxime as reactivators of organophosphate-inhibited acetylcholinesterase in vitro: synthesis and structure-reactivity relationships

F Degorre, D Kiffer, F Terrier

Index: Degorre, Francoise; Kiffer, Daniel; Terrier, Francois Journal of Medicinal Chemistry, 1988 , vol. 31, # 4 p. 757 - 763

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Citation Number: 27

Abstract

We have prepared four new oximes, lb-e, which conform to the general structure RCH, COCH= NOH where R= CH, S, CH, SO, CH, S02, and (CH3) 2Sf, respectively, and have the same E configuration as the parent 2-oxopropanal oxime la (R= H, MINA). The pK, values range from 6.54 (le) to 8.16 (lb), as compared with 8.30 for la. Rates of reaction (k,) with 4- nitrophenyl acetate indicate that the oximate anions have a much higher nucleophilicity ...