55138-39-1Relevant academic research and scientific papers
Crystal structure, spectroscopic studies and theoretical studies of thiobarbituric acid derivatives: understanding the hydrogen-bonding patterns
Sharma, Anamika,Zamisa, Sizwe J.,Noki, Sikabwe,Almarhoon, Zainab,El-Faham, Ayman,Torre, Beatriz G. de la,Albericio, Fernando
, p. 1703 - 1714 (2018)
In addition to their wide-ranging applications in the pharmaceutical industry, thiobarbituric acid (TBA) derivatives are also known to possess applications in engineering and materials science. 20 TBA derivatives, with diversity at the N and C-5 positions through acylation, Schiff base formation, Knoevenagel condensation, thioamide and enamine formation, were studied. The absolute configurations for six derivatives, namely 5-acetyl-1,3-diethyl-2-thioxodihydropyrimidine-4,6(1H,5H)-dione, C10H14N2O3S, A01, 1,3-diethyl-5-propionyl-2-thioxodihydropyrimidine-4,6(1H,5H)-dione, C11H16N2O3S, A02, tert-butyl [1-(1,3-diethyl-4,6-dioxo-2-thioxohexahydropyrimidin-5-yl)-3-methyl-1-oxobutan-2-yl]carbamate, C18H29N3O5S, A06, 1,3-diethyl-4,6-dioxo-2-thioxo-N-(p-tolyl)hexahydropyrimidine-5-carbothioamide, C16H19N3O2S2, A13, 5-(1-aminoethylidene)-1,3-diethyl-2-thioxodihydropyrimidine-4,6(1H,5H)-dione, C10H15N3O2S, A17, and 5-(1-aminopropylidene)-1,3-diethyl-2-thioxodihydropyrimidine-4,6(1H,5H)-dione, C11H17N3O2S, A18, were confirmed by single-crystal X-ray crystallography, which indicates the formation of intramolecular hydrogen bonding in all six cases and intermolecular hydrogen bonding for A17. In A13, the presence of two intramolecular hydrogen bonds was observed. The stabilization of the enol form over the keto form was confirmed by computation. In order to convert the keto form to the enol form, an energy barrier of 55.05 kcal mol?1 needs to be overcome, as confirmed by transition-state calculations.
Exploiting the Thiobarbituric Acid Scaffold for Antibacterial Activity
Sharma, Anamika,Noki, Sikabwe,Zamisa, Sizwe J.,Hazzah, Heba A.,Almarhoon, Zainab M.,El-Faham, Ayman,de la Torre, Beatriz G.,Albericio, Fernando
, p. 1923 - 1930 (2018)
Thiobarbituric acid (TBA) has been considered a privileged structure for developing antimicrobial agents. Diversity was obtained at positions N and at C5 through acylation, Schiff base formation, Knoevenagel condensation, and thioamide and enamine formation. The present work describes the synthesis of small libraries based on the TBA moiety and above-mentioned reactions. Preliminary antimicrobial activity screening of the prepared compounds against selected bacteria (both Gram-positive and -negative) showed the best results for the Boc-Phe-TBA derivative. These results could be useful for designing and building libraries based on other amino acids with distinct protecting groups.
Synthesis and characterization of the novel pyrimidine’s derivatives, as a promising tool for antimicrobial agent and in-vitro cytotoxicity
Abd-Elaziz, Arwa M.,Aly, Hala M.,Fouad, Sawsan A.,Fouda, Amr,Ismail, Abla A.,Saleh, Nashwa M.
, (2021/11/22)
Herein, the biological activities including antibacterial, antifungal, and?in-vitro cytotoxicity for some novel substituted pyrazolo[3,4-d]pyrimidinone, benzylidene dihydropyrimidine, pyrano[2,3-d]pyrimidine, hexahydropyrimido[4, 5-d]pyrimidinone, tetrahydropyrido[2,3-d]pyrimidine-6-carbonitrile, and pyrido[2, 3-d:6,5-d'] dipyrimidinone derivatives were investigated. The synthesized novel compounds were achieved through the incorporation of the active moieties such as halo compound, pyrazolo, pyrano, pyrimido, pyrido-derivatives with active methylene group in thiobarbituric acid derivatives at C-5. Structures of all synthesized compounds were characterized by spectral techniques including IR, 1H-NMR, MS, and 13C-NMR. All synthesized compounds were screened for their antibacterial and antifungal activity, while the most promising compounds were selected to investigate their in-vitro cytotoxic efficacy against normal Vero cells and cancerous Caco-2 cells. Data showed that the biological activities were concentration-dependent. All novel pyrimidine derivatives exhibited broad-spectrum antimicrobial activity with a varied zone of inhibition ranging between 11.3 ± 0.6 and 25.3 ± 0.6?mm. The MIC values are different according to a pathogenic organism (ranging between 3.91 and 500?μg?mL?1), whereas the MBC/MFC were 2 × to 4 × MIC value. Data of in-vitro cytotoxicity confirm the efficiency of selected novel pyrimidine derivatives to target Caco-2 cancerous cells at low concentrations more Vero normal cells. Four selected compounds 4, 7b, 10, and 12 displayed IC50 values of 286.73 ± 4.54, 138.07 ± 8.21, 332.48 ± 18.75, and 241.18 ± 15.60?μg?mL?1, respectively, for normal Vero cell line, whereas it was 271.55 ± 3.68, 65.94 ± 2.36, 121.16 ± 4.96, and 82.28 ± 4.08?μg?mL?1, respectively, for Caco-2 cancerous cell line.
An efficient acylation/base-catalyzed cyclization of thioureas affords N,N′-disubstituted thiobarbituric acids
Heath, Perry C.,Huang, Charles Q.,Lowe, Richard F.,McCarthy, James R.,Weigel, Leland O.,Whitten, Jeffery P.
, p. 1607 - 1610 (2007/10/03)
Acylation of 1,3-disubstituted thioureas with methyl malonyl chloride followed by base-catalyzed cyclization leads to the preparation of 1,3-disubstituted-2-thiobarbituric acids in high yield.
