Preparation of Antidotes for Anticholinesterase Poisoning: Ii. Tertiary and Quaternary Salts of Parpanit and Parpanit Analogues

Abstract

potassium methane disulphonate. The e.s.r. spectra are similar for all these compounds, consisting of a single absorption line with a g value of 2.004. The authors (3) present evidence indicating that the e.s.r. spectra are due to the presence of sulphite free-radical ions. The g values found in the present work are significantly higher than the value of 2.004 reported by Chantry et al. Hence it would appear that if the interpretation of these authors is correct the spectra obtained in the present work are not due to sulphite freeradical ions. Clark et al. (4) suggested that the SOz-free-radical ion was responsible for the e.s.r. spectra obtained by them from X-irradiated sodium and potassium dithionites. The spectra obtained in the present work for y-irradiated thiosulphates are similar to those obtained by Clark et al. As a check, a sample of sodium dithionite was irradiated with CoGo y rays. The e.s.r. spectra of the irradiated sample, a t room temperature and a t liquid nitrogen temperature, were obtained. At the lower temperature the sample could be readily power saturated. At both temperatures the g value of the peak was 2.005 and the line width was 10.4 gauss. The values reported by Clark et al. are 2.005 and 11.5 gauss, respectively.On the basis of the similarity of the e.s.r. spectra of irradiated dithionites and thiosulphates it seems safe to tentatively assume that Sop-free-radical ions are produced in the gamma irradiation of thiosulphates.T h e g value for the low-field shoulder of the low-field structure observed in the e.s.r. spectra of anhydrous IKazSp03 is 2.032. Free radicals in which the odd electron is mainly involved with the sulphur atom may be responsible for this structure ( 2 ) . Low-field structures a t a similar g value have been noted in the e.s.r. spectra of sulphur dissolved oleum (5) and of chilled sulphur vapor (6). Such a conclusion is consistent with the observation that colloidal sulphur is formed when gamma-irradiated thiosulphates are dissolved in water. ACKNOIVLEDGMENTThe authors gratefully acknowledge financial assistance from the Sational Research Council of Canada in the form of a research grant.1.

Preparation of antidotes for anticholinesterase poisoning. IV. Synthesis and protective effectiveness of 2′-(cis- and trans-2″-hydroxycyclohexyl)aminoethyl 1-phenylcyclopentanecarboxylate hydrochlorides

“…We have previously examined methods for the synthesis of Parpanit and its analogues (8)(9)(10) and considered that the most expedient route to the desired compounds would likely be provided by the interaction of a 2'-haloethyl l-phenylcyclopentanecarboxylate with the requisite transand cis-2-aminocyclohexanol. Before embarking on the synthesis of the desired compounds, optimum conditions for the reaction between 2'-bromoethyl 1-phenylcyclopentanecarboxylate and diethylamine in benzene were determined and the resultant yield of Parpanit was 80 %.…”