103293-55-6Relevant academic research and scientific papers
Studies on cerebral protective agents. I. Novel 4-arylpyrimidine derivatives with anti-anoxic and anti-lipid peroxidation activities
Kuno,Sugiyama,Katsuta,Kamitani,Takasugi
, p. 1452 - 1461 (2007/10/02)
Novel 4-arylpyrimidine derivatives were synthesized by the oxidation of 4-aryl-1,4-dihydropyrimidines, and their effects on anti-anoxic (AA) activity in mice and anti-lipid peroxidation (ALP) activity in rat brain mitochondria were investigated. Among these compounds, ethyl 6-methyl-2-phenyl-4-(4-pyridyl)-5-pyrimidinecarboxylate (4b) has AA activity (10mg/kg, i.p.) and ethyl 6-methyl-4-(3-nitrophenyl)-2-phenyl-5-pyrimidinecarboxylate (4f) has ALP activity (73% inhibition at 10-5 g/ml). The latter compound (100mg/kg, i.p.) was also effective on arachidonate-induced cerebral edema in rats with comparable potency to that of vitamin E.
Pyrimidine derivatives, processes for preparation thereof and composition containing the same
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, (2008/06/13)
The invention relates to pyrimidine derivatives and their pharmaceutically acceptable salts which are useful in the treatment of cerebrovascular diseases, to processes for preparation thereof and to the composition containing the same, said pyrimidine der
Dihydropyrimidines. Part 6. 5-Acetyldihydropyrimidines via Condensation of Olefinic Acetylacetones with Amidines. Reinvestigation of Ruhemann's Reaction.
Weis, Alexander L.,Frolow, Felix
, p. 83 - 90 (2007/10/02)
The condensation of benzylideneacetylacetone and benzylamidine, studied by Ruhemann in 1903, has been reinvestigated in detail, and several new reaction products have been isolated and identified.The influence of varying the conditions of reaction have been studied.By using an aprotic solvent (benzene) with azeotropic removal of the water released, for example, the reaction is directed towards formation of 5-acetyldihydropyrimidine (5a).This compound has been obtained in better yields with a two-step approach: initial preparation of the 5-acetyl-6-hydroxytetrahydropyrimidine intermediate (4a), followed by dehydration in acidic media.While this tetrahydropyrimidine in CDCl3 solution most probablyexists as a mixture of the 1,4,5,6-tetrahydro and 3,4,5,6-tetrahydro compounds, crystallization from acetone gave single crystals of 5-acetyl-6-hydroxy-3,4,5,6-tetrahydropyrimidine (4aB) and water in the ratio 2:1.Using the two-step procedure, other tetrahydro- and dihydro-pyrimidine derivatives have been prepared from m-nitrobenzylideneacetylacetone and benzamidine.The reaction has also been explored using acetamidine.All isolated 5-acetyldihydropyrimidines exist in the solid state in the 1,4-dihydro form.However, in solution amidinic tautomerism was observed, which also favours the 1,4-dihydro tautomer.These newly prepared dihydropyrimidines easily undergo oxidation to the corresponding pyrimidines The mechanism of the basic deacetylation observed by Ruhemann in ethanolic solutions, affording the 5-unsubstituted dihydropyrimidine, is also discussed.
