Imidazolium chloride organophosphate antidotes

Abstract

The structures of four imidazolium oxime derivatives were solved by direct methods. These compounds have been shown to be effective in the treatmen of organophosphate poisoning. Despite substantial differences in the nature of the substituent on N1, all four compounds have similar shapes when viewed down the plane of the imidazole ring. The potency of these compounds in the treatment of organophosphate poisoning correlates well with the distance between the imidazole ring and the oxygen moiety on the side chain. 2-(hydroxyimino)methyl-3-methyl-1-[1-(3-methyl-sulfonylpropyloxy) methyl]imidazolium chooride (1) crystallizes in the triclinic space groupPī (Z=2). The unit cell parametersa, b, c (Å) and α, β, and γ (^o) were: 8.506(2), 8.787(4), 10.070(4), 73.68(3), 81.37(3), 85.39(3). 2-(hydroxyimino)-methyl-3-methyl-1-(2′-N-phenylsulfonylamino-1′-ethyl) imidazolium chloride (2) crystallizes in the monoclinic space groupP2 ₁ la(Z=4). The unit cell parametersa, b, c (Å) and β (^o) were: 12.690(2), 6.317(4), 20.193(4), 91.47(2). 1-(2′-ethyl-2′-trifluoromethanesulfonyl-aminoethyl)-2-(hydroxyimino) methyl-3-methylimidazolium chloride (3) crystallizes in the triclinic space groupPī (Z=2). The unit cell parametersa, b, c (Å) and α, β, and γ (^o) were: 6.635(1), 11.333(2), 12.274(3), 115.05(3), 98.46(3), 90.11(3). 2-(hydroxyimino)-methyl-3-methyl-1-[2-(2-methyl-3-nitrobutyloxy) methyl]-imidazolium chloride (4) crystallizes in the orthorhombic space groupP2₁2₁2₁ (Z=4). The unit cell parametersa, b, andc (Å) were: 10.034(1), 11.401(2), 13.352(2).