Reactivation of Aged Organophosphorus Inhibited Acetylcholinesterase

Abstract

The purpose of this work is to prepare derivatives of 2-PAM that are substituted in the 3-position by groups capable of bonding to, or liganding with, the oxygen on the phosphorus of aged, poisoned (by phosphorylation or phosphonylation) acetylcholinesterase. The derivatives suggested for preparation are designed to facilitate cleavage of the bond between phosphorus and the oxygen of the serine in the active site of the poisoned acetylcholinesterase and to thus regenerate native enzyme. The major effort in this first year has been development of a general route to these previously unknown oximes. That route, beginning with derivatives of 3-aminocrotonate and acrolein, has now been defined. Additionally, using the successful route, one compound has been prepared and submitted (i.e., ethyl pyridine-3-acetate 2-carboxaldehyde oxime methiodide, BL19566), another prepared (i.e., t-butyl pyridine-3-carboxylate 2- carboxaldehyde oxime methiodide) but not submitted (because the methochloride, not the methiodide as originally anticipated, is desired and anion exchange has not yet succeeded), and significant quantities of intermediates for other proposed compounds have been generated. Keywords: Pyridine oximes.

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Document Details

Document Type
Technical Report
Publication Date
Aug 31, 1986
Accession Number
ADB110083

Entities

People

  • David R. Dalton

Organizations

  • Temple University

Tags

DTIC Thesaurus Topics

  • Acids
  • Acroleins
  • Alcohols
  • Aldehydes
  • Anhydrides
  • Chemical Synthesis
  • Chemistry
  • Chlorides
  • Hydroxides
  • Ion Exchange
  • Materials
  • Organic Chemistry
  • Phosphonic Acids
  • Sodium Compounds

Fields of Study

  • Chemistry

Readers

  • Analytical Chemistry
  • Neurotoxicology
  • Systems Analysis and Design