104169-72-4Relevant academic research and scientific papers
The influence of sulfur substituents on the mol-ecular geometry and packing of thio derivatives of N-methyl-phenobarbital
Janik, Alicja,Olech, Andrzej,Stasiewicz-Urban, Anna,Stadnicka, Katarzyna
, p. o70-o75 (2009)
The room-temperature crystal structures of four new thio derivatives of N-methyl-phenobarbital [systematic name: 5-ethyl-1-methyl-5-phenyl-pyrimidine-2, 4,6(1H,3H,5H)-trione], Cl3H14N2O3, are compared with the structure of the parent
Kinetics of Hydrolysis of N-Methyl-2,4-dithiophenobarbital
Tarsa, Monika,Starek, Ma?gorzata,Zuchowski, Grzegorz,Stasiewicz-Urban, Anna,Ceg?a, Marek
, p. 89 - 97 (2016/01/26)
The rate of hydrolytic degradation of N-methyl-2,4-dithiophenobarbital by spectrophotometric and separation methods was studied. The rate constants, order of reaction, activation energy, and pKa values were calculated based on the measurements of absorbance in the UV range. The changes in the absorbance values over time for solutions of different pH were analysed. Based on the obtained results, it was found that the hydrolysis of N-methyl-2,4-dithiophenobarbital followed the kinetics of a pseudo-first order reaction. Plots illustrating dependences, log k, and pH indicate the catalytic effect of OH- ions on the occurring process. The results show that in an alkaline environment the pyrimidine ring undergoes cleavage in the 1-6 position, and gradual desulfurization. The obtained results were compared with data for phenobarbital, 2-thiophenobarbital, and 2,4-dithiophenobarbital. It can be concluded that the change of an oxygen atom to a sulfur atom in the ring of a barbituric acid derivative causes an easier decomposition of the compound. However, the insertion of a methyl group on the nitrogen atom increases the durability of the compound.
Synthesis of thio derivatives of phenobarbital and its N-methyl derivatives
Stasiewicz-Urban,Kubaszek,Zylewski,Cegla,Bojarski
, p. 2105 - 2115 (2007/10/03)
Differently substituted thio derivatives of phenobarbital and its N-mono- and N,N′-dimethyl derivatives were obtained by thionation of respective substrates with Lawesson's reagent. The structure of the products not described in the literature was confirmed by spectral and elemental analyses. The spectral properties allow to differentiate between positional isomers of the products.
Methylation of 5-ethyl-5-phenyl-2-thioxo-4,6(1H,3H,5H)-pyrimidinedione
Kubaszek, M.,Paluchowska, M.,Chmiel, E.,Bojarski, J.
, p. 117 - 124 (2007/10/02)
Methylation of the title compound (2-thiophenobarbital) under different conditions yielded two pairs of isomeric N-, and S--monomethyl and N,N'- and N,S-dimethyl derivatives.Spectral data confirm their structure and allow to identify the methyl substitution.Preliminary results of irradiation of N-CH3 substituted compounds are also presented. Key words: pyrimidines, sulfur compounds, 2-thiobarbiturate
N-Alkyl barbiturates. A series of compounds for the study of metabolic structure-activity relationships
Treston,Hooper
, p. 1627 - 1629 (2007/10/02)
Many therapeutic agents are metabolised along multiple pathways, but up to now there have been few investigations addressing the question of which chemical features of drugs govern the participation in, and quantitative significance of, different biotransformation pathways. To assess the influence of variations of the chemical structure upon metabolim, a series of novel barbiturate analogues has been synthesized. The N1-monoalkylated and N1,N2-dialkylated phenobarbitones and 2-desoxyphenobarbitones have been synthesized via condensation of ethylphenylmalonic acid derivatives with different N-alkylated ureas or thioureas, and/or by base-catalyzed N-alkylation of different barbituric acids.
