Metabolism of Drugs. XXX. The Biotransformation of Drugs having Cyclohexene Ring.(3). The Synthesis and Metabolism of 5-Ethyl-5-(1-cyclohexenyl)-4, 6-dioxohexahydropyrimidine

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5-Ethyl-5-(1-cyclohexenyl)-4, 6-dioxo-hexahydropyrimidine (ECP), which had beenexpected to display anticonvulsant activity, was prepared by the hydrogenolysis of the corresponding 2-thiobarbituric acid with Raney nickel catalyst, and the mechanism of its biotransformation was discussed.<BR>The transformation of the cyclohexenyl group in 2-thiobarbituric acid derivatives to a cyclohexyl group did not take place when Raney nickel catalyst was prepared by the method of Mozingo.<BR>5-Ethyl-5-(1-cyclohexenyl)-4, 6-dioxo-hexahydropyrimidine (m.p. 269-270°) was obtained in an excellent yields. When administered to rabbits, ECP was partly biotransformed into a metabolite and partly excreted intact in their urine. This metabolite wan confirmed to be 5-ethyl-5-(3'-oxo-1'-cyclohexenyl) barbituric acid by admixture with the oxidation product of ethylhexabit with chromimum trioxide. The characterization and identification of the unchanged ECP as well as a metabolite 5-ethyl-5-(3'-oxo-1'-cyclohexenyl) barbituric acid, were also performed by the color reactions with copper-pyridine and cobaltous nitrate-ammonia, by the paper chromatography, and by the measurement of the ultraviolet and infrared absorption spectra.

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