35221-12-6Relevant academic research and scientific papers
Barbiturate squaraine dyes as fluorescent probes for serum albumins detection
Almeida, Paulo,Boto, Renato E. F.,Gomes, Vanessa S. D.,Gon?alves, Helena M. R.,Reis, Lucinda V.
, (2020/07/02)
Three indolenine-based barbiturate squaraine dyes were synthesized, characterized and subjected to photophysical studies, including their affinity with human serum albumin and bovine serum albumin as protein models in phosphate buffer solution. All dyes successfully interact with both proteins with high affinity binding constants. It was found that dyes with hydrophobic substituents had superior binding constants with both proteins. The fluorescence intensity of all dyes increased in the presence of both proteins which allowed the determination of detection and quantifications limits in the tens of nanomolar, using a protein concentration of 0–3.5 μM. Concerning to the study on the binding sites of the synthesized dyes using the warfarin and ibuprofen markers, the results of this study suggest that, one dye binds to both BSA binding sites while the two others dyes binds only to site I, and that all three dyes bind to both HSA binding sites.
Trisubstituted barbiturates and thiobarbiturates: Synthesis and biological evaluation as xanthine oxidase inhibitors, antioxidants, antibacterial and anti-proliferative agents
Figueiredo, Joana,Serrano, Jo?o L.,Cavalheiro, Eunice,Keurulainen, Leena,Yli-Kauhaluoma, Jari,Moreira, Vania M.,Ferreira, Susana,Domingues, Fernanda C.,Silvestre, Samuel,Almeida, Paulo
, p. 829 - 842 (2017/12/13)
Barbituric and thiobarbituric acid derivatives have become progressively attractive to medicinal chemists due to their wide range of biological activities. Herein, different series of 1,3,5-trisubstituted barbiturates and thiobarbiturates were prepared in moderate to excellent yields and their activity as xanthine oxidase inhibitors, antioxidants, antibacterial agents and as anti-proliferative compounds was evaluated in vitro. Interesting bioactive barbiturates were found namely, 1,3-dimethyl-5-[1-(2-phenylhydrazinyl)ethylidene]pyrimidine-2,4,6(1H,3H,5H)-trione (6c) and 1,3-dimethyl-5-[1-[2-(4-nitrophenyl)hydrazinyl]ethylidene]pyrimidine-2,4,6(1H,3H,5H)-trione (6e), which showed concomitant xanthine oxidase inhibitory effect (IC50 values of 24.3 and 27.9 μM, respectively), and 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging activity (IC50 values of 18.8 and 23.8 μM, respectively). In addition, 5-[1-(2-phenylhydrazinyl)ethylidene]pyrimidine-2,4,6(1H,3H,5H)-trione (6d) also revealed DPPH radical scavenger effect, with an IC50 value of 20.4 μM. Moreover, relevant cytotoxicity against MCF-7 cells (IC50 = 13.3 μM) was observed with 5-[[(2-chloro-4-nitrophenyl)amino]methylene]-2-thioxodihydropyrimidine-4,6(1H,5H)-dione (7d). Finally, different 5-hydrazinylethylidenepyrimidines revealed antibacterial activity against Acinetobacter baumannii (MIC values between 12.5 and 25.0 μM) which paves the way for developing new treatments for infections caused by this Gram-negative coccobacillus bacterium, known to be an opportunistic pathogen in humans with high relevance in multidrug-resistant nosocomial infections. The most promising bioactive barbiturates were studied in silico with emphasis on compliance with the Lipinski's rule of five as well as several pharmacokinetics and toxicity parameters.
Pharmacophore Hybridization to Discover Novel Topoisomerase II Poisons with Promising Antiproliferative Activity
Ortega, Jose Antonio,Riccardi, Laura,Minniti, Elirosa,Borgogno, Marco,Arencibia, Jose M.,Greco, Maria L.,Minarini, Anna,Sissi, Claudia,De Vivo, Marco
supporting information, p. 1375 - 1379 (2018/02/17)
We used a pharmacophore hybridization strategy to combine key structural elements of merbarone and etoposide and generated new type II topoisomerase (topoII) poisons. This first set of hybrid topoII poisons shows promising antiproliferative activity on hu
5-CARBOXAMIDE-2-THIOBARBITURIC ACIDS AND USE THEREOF AS MEDICAMENTS
-
Page/Page column 13; 16, (2018/10/19)
The invention relates to a class of 5-carboxamide-2-thiobarbituric acid derivatives which inhibits human type II topoisomerase (topoII) enzyme and to use thereof as medicaments especially for blocking the proliferation of cancer cells and treating cancer.
A synthetic route to novel 3-substituted-2,1-benzisoxazoles from 5-(2-nitrobenzylidene)(thio)barbiturates
Serrano, Jo?o L.,Cavalheiro, Eunice,Barroso, Sónia,Rom?o, Maria J.,Silvestre, Samuel,Almeida, Paulo
, p. 990 - 995 (2017/11/27)
2,1-Benzisoxazoles, also called anthranils, are one of the two types of aromatic bicyclic heterocycles having a benzene ring fused with an isoxazole, which are particularly recognized as valuable intermediates in organic synthesis. Nevertheless several methods can be found in the literature to prepare 2,1-benzisoxazoles, we herein report a new, efficient, simple, mild, and alternative procedure to prepare 3-substituted-2,1-benzisoxazoles from 5-(2-nitrobenzylidene)barbiturates in moderate to good yields (51–82%). All the novel benzisoxazoles showed spectral data fully consistent with the assigned structures, which were unequivocally confirmed by single crystal X-ray analysis. A possible mechanism of the reaction is proposed. In addition, a screening of the bioactivity of these benzisoxazoles as xanthine oxidase inhibitors, antioxidants, and cytotoxic compounds was performed. The benzisoxazole formed from barbituric acid revealed moderate xanthine oxidase inhibitory effects (IC50 = 22.10 μM).
A sulfur on behalf of the barbituric acid derivative for the probe molecule detecting secondary amine method and its preparation
-
Paragraph 0048, (2018/01/19)
The invention discloses a method for detecting secondary amine with thiobarbituric acid derivatives (TBAs) serving as ultraviolet-visible light (UV-vis) spectrophotometric method probe molecules and preparation of the thiobarbituric acid derivatives for detecting secondary amine. The probe molecules are prepared from primary amine through a preparation line of a system. The probe molecules are provided with a furan ring (or thiophene ring) for recognizing secondary amine, an independent probe molecule solution is yellow, and along with addition of secondary amine, the solution becomes red from yellow. A molecular probe is high in selectivity and sensitivity to secondary amine, the response range to secondary amine is 100 micrometers to 400 micrometers, and the limit of detection (LOD) is 12 micrometers. Test paper can be prepared from the probe molecules, and qualitative detection on secondary amine can be achieved fast with low cost. The method can be widely applied to fast and sensitive detection such as online detection of secondary amine compounds, food analysis and environmental monitoring in the industrial process.
Synthesis of biginelli products of thiobarbituric acids and their antimicrobial activity
Dabholkar, Vijay V.,Ravi, Tripathi Dilip
body text, p. 1033 - 1040 (2011/02/23)
A simple and efficient method has been developed for the synthesis of 2,4,7-tri(substituted)phenyl-2,4,8,10-tetraza-3,9-dithioxo-5-oxobicyclo-[4.4.0] dec-1(6)-ene (4) and 2,4,7-tri(substituted)phenyl-2,4,8,10-tetraza-3-thioxo-5,9- dioxobicyclo[4.4.0]dec-1
One or two step acid mediated cyclocondensation process for the preparation of 5-carbethoxy-2-thiouracils from diethyl ethoxymethylenemalonate and thioureas
Botsi, Sofia,Tsolomitis, Athanase
, p. 229 - 234 (2008/03/14)
An acid mediated synthesis of 5-carbethoxy-2-thiouracils via an one step cyclocondensation of diethyl ethoxymethylenemalonate and thioureas or the under milder reaction conditions, also obtained, thioureidomethylenemalonates, is described here.
Chemical modification of plant alkaloids. 2. Reaction of cotarnine with barbituric acid derivatives and structure of 5-dihydrocotarnylbarbituric acids
Krasnov,Kartsev,Yurova
, p. 543 - 550 (2007/10/03)
The reaction of barbituric acid and its N-substituted derivatives and 2-thio analogs with cotarnine forms 5-(4-methoxy-6-methyl-5,6,7,8-tetrahydro-2H-1,3-methylenedioxy-[4,5-g]isoquinolinyl-1)barbituric acids, a new class of zwitter-ions, the structure of which was studied by 1H and 13C NMR spectroscopy and mass spectrometry. The prepared compounds exist in solution as stable intermolecular associates and have a complicated H-bonded structure.
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.
