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Supramolecular structure of new phenacyloxime derivative of piridoxal oxime

In the past few decades, a whole series of aliphatic, aromatic and heterocyclic oximes have been synthesized and tested as antidotes in poisoning with organophosphorus compounds (OPC). Among them only mono‐ and bis‐pyridinium compounds possessing an oxime group in position 2 and 4 (PAM‐2, TMB‐4, HI‐6) have been used in human therapy. Reactivating action of these compounds is due to the quaternary nitrogen of the pyridine ring and to the oxime groups which make possible the rupture of the phosphorylated enzyme and its reactivation. Compounds that possess quaternary pyridinium nitrogen and an oxime group, but in the aliphatic part of the molecule, are also synthesized. Malatesta et al. have synthesized 1‐phenacyloxime quinoline chloride, which proved to be a better in vitro reactivator of cholinestrase inhibited by sarin then PAM‐2. Binenfeld et al. synthesized derivatives of 1‐phenacyloxime quinoline chloride and showed that the replacement of the pyridine ring by quinoline analogue produces an enhancement of its inhibitory effect on ChE and also makes it possible to reactivate ChE inhibited by sarin 1. Hankonyi et al. prepared 1‐phenacyloxime‐pyridinium chloride and 2‐ methyl and 4‐methylpyridinium derivatives 2. In this work we present supramolecular structure of new dioxime, 3‐hydroxy‐1‐((2‐ (hydroxyimino)‐2‐phenylethyl)‐4‐ (hydroxyiminomethyl)‐5‐(hydroxymethyl)‐2‐ methylpyridin‐ 1‐ium bromide (1), prepared by quaternisation of pyridoxaloxime with phenacyloxime bromide (Figure 1a). It will be shown that cations and anions in 1 form a complex network of hydrogen bonds and a three‐dimensional network (Figure 1b).

piridoxal oxime, supramolecular structure

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