27402-47-7Relevant articles and documents
A method for rapid synthesis of 18Olabeled aldehyde compounds
-
Paragraph 0010-0011, (2022/01/12)
The present invention discloses a method for rapid synthesis of 18O labeled aldehyde compounds, first the aldehyde compound and barbituric acid was added to ethanol, reacted at 40 ~ 60 ° C for 10 to 12 h, to obtain precipitation, cooled to room
A study on the physical properties of low melting mixtures and their use as catalysts/solvent in the synthesis of barbiturates
Theresa, Letcy Vincent,Avudaiappan, Govindan,Shaibuna, Machingal,Hiba, Kottayil,Sreekumar, Krishnapillai
, p. 1849 - 1860 (2021/06/17)
In recent years, deep eutectic solvents have become attractive due to their interesting characteristics such as, physicochemical properties, low cost of components, easiness to prepare, low toxicity, bio-renewability, and biodegradability. In order to make the deep eutectic mixture more cost-effective and renewable, carbohydrate derivatives were linked with deep eutectic mixtures, since, carbohydrates are the most important and widespread renewable compounds on the earth. In this work, we have used low melting mixtures comprised of carbohydrates to create the reaction media for organic transformations. The physical properties such as density, viscosity, acidity, refractive index, surface tension, solubility, glass transition temperature, thermal stability, solvent polarity, and toxicity of the mixture were studied. Low melting mixtures were used as reaction media and catalysts for the effective synthesis of Barbiturates. The reaction between aldehydes and barbituric acid/thiobarbituric acid, and the reaction between aldehydes, barbituric acid/thiobarbituric acid, and malononitrile/dimedone were performed effectively with good to excellent yields. The recyclability of the catalyst/solvent was also established.
Knoevenagel condensation in aqueous media promoted by 2,2′-bipyridinium dihydrogen phosphate as a green efficient catalyst
Darvishzad, Shila,Daneshvar, Nader,Shirini, Farhad,Tajik, Hassan
, p. 2973 - 2984 (2021/04/19)
A 2,2′-Bipyridine-based ionic compound named 2,2′-bipyridinium dihydrogen phosphate was synthesized by addition of phosphoric acid to a solution of 2,2′-Bipyridine in dichloromethane. After the characterization using FT-IR, mass, 1H, 13C and 31P NMR techniques, it was used as a Bronsted dicationic acidic catalyst for the promotion of the synthesis of 2-arylidene malononitrile and 5-arylidene barbituric acid derivatives via Knoevenagel condensation reaction in water. Some of the advantages of this method are the utilization of an easy preparable, cost-effective and eco-friendly organic salt as a catalyst within high rates and yields of the reactions, simple and quick work-up and acceptable reusability of the catalyst.
Assessing the potential of para-donor and para-acceptor substituted 5-benzylidenebarbituric acid derivatives as push–pull electronic systems: Experimental and quantum chemical study
Stojiljkovi?, Ivana N.,Ran?i?, Milica P.,Marinkovi?, Aleksandar D.,Cvijeti?, Ilija N.,Mil?i?, Milo? K.
supporting information, (2021/02/26)
Electronic interactions in donor-π-linker-acceptor systems with barbituric acid as an electron acceptor and possible electron donor were investigated to screen promising candidates with a push–pull character based on experimental and quantum chemical studies. The tautomeric properties of 5-benzylidenebarbituric acid derivatives were studied with NMR spectra, spectrophotometric determination of the pKa values, and quantum chemical calculations. Linear solvation energy relationships (LSER) and linear free energy relationships (LFER) were applied to the spectral data - UV frequencies and 13C NMR chemical shifts. The experimental studies of the nature of the ground and excited state of investigated compounds were successfully interpreted using a computational chemistry approach including ab initio MP2 geometry optimization and time-dependent DFT calculations of excited states. Quantification of the push–pull character of barbituric acid derivatives was performed by the 13CNMR chemical shift differences, Mayer π bond order analysis, hole-electron distribution analysis, and calculations of intramolecular charge transfer (ICT) indices. The results obtained show, that when coupled with a strong electron-donor, barbituric acid can act as the electron-acceptor in push–pull systems, and when coupled with a strong electron-acceptor, barbituric acid can act as the weak electron-donor.
Three Resorcin[4]arene-Based Two-Dimensional Zn(II) Supramolecular Isomers Synthesized via a Structure-Directing Strategy for Knoevenagel Condensation
Wang, Fei-Fei,Liu, Ying-Ying,Pei, Wen-Yuan,Ma, Jian-Fang
supporting information, p. 7329 - 7336 (2021/05/29)
Herein, in the presence of three structure-directing agents (SDAs), a family of imidazole-functionalized resorcin[4]arene-based coordination polymers (CPs), [Zn(TIC4R)(HCOO)]·HCOO·0.5DMF·1.5H2O (1), [Zn(TIC4R)(CN)]·HCOO·DMF·2.5H2O (2), and [Zn(TIC4R)(H2O)
BARBITURIC ACID DERIVATIVES AS SELF-TANNING SUBSTANCES
-
Paragraph 0226, (2020/02/20)
The present invention relates to the use of barbituric acid derivatives of the formula I as self-tanning substance, for increasing melanin synthesis, for improving melanin transport and/or improving the distribution of melanin in superbasal layers, to preparations comprising these barbituric acid derivatives, and to specific barbituric acid derivatives.
Antifibrotic Effects of a Barbituric Acid Derivative on Liver Fibrosis by Blocking the NF-κB Signaling Pathway in Hepatic Stellate Cells
Chen, Tzu-Lang,Hsu, Ming-Hua,Liao, Yi-Jen,Liu, Chao-Lien,Suk, Fat-Moon,Twu, Yuh-Ching,Wang, Yuan-Hsi
, (2020/04/21)
Hepatic stellate cells (HSCs) are the major profibrogenic cells that promote the pathogenesis of liver fibrosis. The crosstalk between transforming growth factor-β1 (TGF-β1) signaling and lipopolysaccharide (LPS)-induced NF-κB signaling plays a critical role in accelerating liver fibrogenesis. Until now, there have been no FDA-approved drug treatments for liver fibrosis. Barbituric acid derivatives have been used as antiasthmatic drugs in the clinic; however, the effect of barbituric acid derivatives in treating liver fibrosis remains unknown. In this study, we synthesized a series of six barbituric acid (BA) derivatives, and one of the compounds, BA-5, exhibited the best ability to ameliorate TGF-β1-induced HSC activation without overt cytotoxic effects. Then, we treated HSCs and RAW264.7 macrophages with BA-5 to analyze the cross-talk of anti-fibrotic and anti-inflammatory effects. Carbon tetrachloride (CCl4)-induced liver fibrosis mouse model was used to evaluate the therapeutic effects of BA-5. Treatment with BA-5 inhibited TGF-β1-induced α-SMA, collagen1a2, and phosphorylated smad2/3 expression in HSCs. Furthermore, BA-5 treatment reversed the LPS-induced reduction in BAMBI protein and decreased IκBα and NF-κB phosphorylation in HSCs. NF-κB nuclear translocation, MCP-1 secretion, and ICAM-1 expression were also inhibited in BA-5-treated HSCs. Conditioned medium collected from BA-5-treated HSCs showed a reduced ability to activate RAW264.7 macrophages by inhibiting the MAPK pathway. In the mouse model, BA-5 administration reduced CCl4-induced liver damage, liver fibrosis, and F4/80 expression without any adverse effects. In conclusion, our study showed that the barbituric acid derivative BA-5 inhibits HSCs activation and liver fibrosis by blocking both the TGF-β1 and LPS-induced NF-κB signaling pathways and further inhibits macrophages recruitment and activation.
Microwave-associate synthesis of Co3O4 nanoparticles as an effcient nanocatalyst for the synthesis of arylidene barbituric and Meldrum's acid derivatives in green media
Yahyazadehfar, Mahdieh,Sheikhhosseini, Enayatollah,Ahmadi, Sayed Ali,Ghazanfari, Dadkhoda
, (2019/08/02)
In this study, Co3O4 nanocatalysts were constructed in environmentally appropriate conditions using controlled, effective, and facile microwave method. The final nanostructures were characterized by SEM, XRD, and TEM analyses. The products had a small size distribution, homogeneous morphology, and crystallographic structures associated with the formation of Co3O4 nanostructures. Moreover, EDS mapping analysis confirmed the existence of Co and O elements in the final structure, and the magnetic properties of the samples were investigated by VSM. The application of this nanostructure in a catalytic process was further examined, and the results suggested that it could be used as a novel candidate for the synthesis of arylidene barbituric and Meldrum,s acid through Knoevenagel condensation of aldehydes by barbituric and Meldrum,s acid in aqueous media. The high yield of these nanocatalysts would be justified by the nature of the nanostructure as well as the experimental procedure developed in this study, which affected the physicochemical features of the products.
Verjuice as a green and bio-degradable solvent/catalyst for facile and eco-friendly synthesis of 5-arylmethylenepyrimidine-2,4,6-trione, pyrano[2,3-d]pyrimidinone and pyrimido[4,5-d]pyrimidinone derivatives
Safari, Niloufar,Shirini, Farhad,Tajik, Hassan
, p. 887 - 897 (2019/03/27)
Verjuice (unripe grape juice), a natural mixture of organic acids, which is identified by pH-metric and TGA analysis, is efficiently used for the promotion of the synthesis of 5-arylmethylenepyrimidine-2,4,6-triones, via Knovenagel condensation reaction between barbituric or thiobarbituric acid and aldehydes. Verjuice is also employed for the effective synthesis of pyrano[2,3-d]pyrimidinone derivatives via a three-component reaction of barbituric acid or its thio analogue, aldehydes and malononitrile. In the same way, pyrimido[4,5-d]pyrimidinone derivatives are simply produced via the reaction of barbituric acid, aldehydes and urea or thiourea in the presence of verjuice. This green methodology rewards notable advantages including simple procedures, acceptable reaction times, easy work-up, high yields, circumventing the use of any expensive starting materials, volatile and hazardous organic solvents during the reaction and work-up process, and use of a natural, low-cost, reusable, and bio-degradable catalyst.
Comparison of the efficiency of two imidazole-based dicationic ionic liquids as the catalysts in the synthesis of pyran derivatives and Knoevenagel condensations
Sharifi, Zahra,Daneshvar, Nader,Langarudi, Mohaddeseh Safarpoor Nikoo,Shirini, Farhad
, p. 4941 - 4958 (2019/07/03)
In the present work, 3,3′-(butane-1,4-diyl)bis(1-methyl-1H-imidazol-3-ium) dichloride ([C4(MIm)2]·2Cl) and 3,3′-(butane-1,4-diyl)bis(1-methyl-1H-imidazol-3-ium) hydrogen sulfate ([C4(MIm)2]·2HSO4) were prepared via adequate, solvent-free methods and characterized using FT-IR, 1H NMR, 13C NMR, and potentiometric titration techniques. These reagents were investigated in the synthesis of 5-arylidene (thio)barbituric acids, 2-arylidene malononitriles, 4H-pyrans, and pyrano[2,3-d] pyrimidineones, and their catalytic activities were compared in the promotion of these reactions. Based on the obtained results, we found that [C4(MIm)2]·2Cl showed more catalytic efficiency where a basic or weak acidic media is needed. In contrast, [C4(MIm)2]·2HSO4 is a powerful catalyst in reactions needing acidic catalysts to enhance the reaction rate. Using these reagents, the products were formed under mild and eco-friendly conditions in excellent yields during short reaction times without needing column chromatography for work-up.
