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. 2007 Aug 20;12(8):1964-72.
doi: 10.3390/12081964.

Targeted synthesis of 1-(4-hydroxyiminomethylpyridinium)-3-pyridiniumpropane dibromide--a new nerve agent reactivator

Kamil Kuca  1 , Kamil Musilek, Martin Paar, Daniel Jun, Petr Stodulka, Martina Hrabinova, Jan Marek
Affiliations

Targeted synthesis of 1-(4-hydroxyiminomethylpyridinium)-3-pyridiniumpropane dibromide--a new nerve agent reactivator

Kamil Kuca et al. Molecules. .

Abstract

Preparation of 1-(4-hydroxy-iminomethylpyridinium)-3-pyridiniumpropane dibromide is described. This compound represents a new acetylcholinesterase (AChE) reactivator, which has no substituents on the second pyridinium ring as found in other commonly used AChE reactivators. The reactivation ability of this reactivator was tested on tabun- and cyclosarin-inhibited AChE. According to the results obtained, the new compound (without substitution and with decreased molecule size) showed increased reactivation potency in case of cyclosarin inhibited AChE. A potent oxime for treatment of tabun and cyclosarin-caused intoxications was thus obtained via slight modification of the reactivator structure (compared to trimedoxime and K027).

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Figures

Figure 1
Figure 1
Organophosphorus inhibitors of acetylcholinesterase known as nerve agents.
Figure 2
Figure 2
Commercially available oxime reactivators.
Figure 3
Figure 3
Novel reactivators designed for nerve agent poisonings.
Scheme 1
Scheme 1
Proposed products via one step synthesis of bisquaternary non-symmetrical acetylcholinesterase reactivator.
Scheme 2
Scheme 2
Two step synthesis of non-symmetrical acetylcholinesterase reactivator.
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