57270-80-1

Upstream product

• 769-42-6 1,3-dimethylbarbituric acid 
• 123-08-0 4-hydroxy-benzaldehyde 
• 6642-31-5 6-Amino-1,3-dimethylbarbituric acid 

Downstream Products

• 110449-08-6 5-(4'-acetoxybenzylidene)-1,3-dimethylbarbituric acid 

Relevant academic research and scientific papers

Application of bioorthogonal hetero-Diels-Alder cycloaddition of 5-arylidene derivatives of 1,3-dimethylbarbituric acid and vinyl thioether for imaging inside living cells

New bioorthogonal cycloaddition of 5-arylidene derivatives of 1,3-dimethylbarbituric acid as 1-oxa-1,3-butadienes and vinyl thioether as a dienophile has been applied to imaging inside living cells. The reaction is high yielding, selective, and fast in aqueous media. The proposed 1-oxa-1,3-butadiene derivative conjugated to a FITC fluorochrome selectively and rapidly labels the cancer cells pretreated with the dienophile-taxol. The second order rate constants k2 for various proposed bioorthogonal cycloadditions were estimated to be in the range from 0.9 × 10-2 M-1 s-1 to 1.4 M-1 s-1, which is much better than in the case of the first generation TQ-ligation (o-quinolinone quinone methide and vinyl thioether ligation, k2 = 1.5 × 10-3 M-1 s-1) and comparable or better to that for the second generation TQ-ligation (k2 = 2.8 × 10-2 M-1 s-1). The reaction rate constants k2 of proposed ligation reactions are in the range of the rate constants k2 for tetrazines and norbornenes or tetrazines and cyclopropenes. These findings indicate that this chemistry is suitable for in vitro imaging experiments.

L-Proline based ionic liquid: A highly efficient and homogenous catalyst for synthesis of 5-benzylidene-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione and pyrano[2,3-d] pyrimidine diones under ultrasonic irradiation

A catalytic, practical, efficient procedure for the synthesis of 5-benzylidene-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione and pyrano[2,3-d] pyrimidine diones at room temperature was developed using L-Proline nitrate ionic liquid under ultrasonic irradiation. The L-Proline nitrate is homogeneous and green catalyst easy to prepare by mixing L-Proline and nitric acid possess excellent catalytic activity under standard ultrasonic bath at room temperature for the synthesis of pyrimidine core. This adequate procedure offers some advantages like the use of green solvent H2O, environmentally green benign procedure, excellent yields, simple procedure, short reaction times, no need for column chromatographic separation and reusability of catalyst for five subsequent reaction.

Efficient one-pot synthesis of some new pyrimido[5′,4′:5,6]pyrido[2,3-d]pyrimidines catalyzed by magnetically recyclable Fe3O4 nanoparticles

The study is devoted to one-pot reaction of 1,3-dimethylbarbituric acid with aromatic aldehydes and ammonium acetate using Fe3O4 nanoparticles as efficient and magnetically recyclable catalysts. Aromatic aldehydes substituted with electron-withdrawing groups or none, reacted successfully with 1,3-dimethylbarbituric acid and ammonium acetate to give new pyrimido[5′,4′:5,6]pyrido[2,3-d]pyrimidine derivatives (can be also named as pyrido[2,3-d:6,5-d′]dipyrimidines) in high yields over relatively short reaction time. The Knoevenagel condensation products were isolated using aromatic aldehydes bearing electron-donating substituents. The catalyst could be efficiently used for four times without substantial reduction in its activity. The new products were characterized on the basis of FT-IR, 1H NMR and 13C NMR spectral data.

“On-water” catalyst-free, one-pot synthesis of quaternary centered and spiro-tetrahydrothiophene-barbiturate hybrids

A green and efficient method have been developed for the synthesis of quaternary centered and spiro-barbiturate-tetrahydrothiophene hybrids via Knoevenagel condensation,1,4-thia-Michael and intramolecular Aldol reactions using “on water” concept under catalyst-free conditions. Systematic studies were carried out to find the role of the water and total reaction concentration (0.086?M) to promote the reaction in two steps (one-pot). The use of water as a reaction medium, catalyst-free conditions, broad substrate scope, one-pot approach for the creation of quaternary centered and spiro molecules are the advantages of this method.

SHIKIMATE PATHWAY INHIBITORS AND THE USE THEREOF

The present invention relates to methods of inhibiting shikimate pathway, comprising administering to a subject a pharmaceutically acceptable composition comprising a compound having a formula: or pharmaceutically acceptable salts thereof. The present invention also provides a synergistic antibacterial composition containing compound

Effect of reaction parameters on the synthesis of 5-arylidene barbituric acid derivatives in ball mills

The influence of crucial reaction parameters on Knoevenagel condensation in planetary ball mills was investigated. Rotation frequency (νrot), milling ball diameter (dMB), milling ball filling degree (φMB), and beaker size

Synthesis of spiro 3-bromo-4,5-dihydroisoxazoles via [1,3]dipolar cycloaddition reactions

A group of novel 4-bromo-7,9-dimethyl-1-aryl-2-oxa-3,7,9-triaza-spiro[4.5]dec-3-ene-6,8,10-trione derivatives is prepared through 1,3-dipolar cycloadditions between benzylidenes and bromonitrile oxide. This reaction is shown to have high atom economy.

Knoevenagel condensation in aqueous micellar media using EDAHS as a new Bronsted acidic ionic liquid

The Knoevenagel condensation between aromatic aldehydes and malononitrile, barbituric acid or 1,3-dimethylbarbituric acid with ethane-1,2-diammonium hydrogen sulfate (EDAHS) in aqueous micellar media, using sodium dodecyl sulfate is described. EDAHS was found to be a highly active and stable Bronsted acidic ionic liquid catalyst under the reaction conditions. Graphical Abstract: [Figure not available: see fulltext.].

Synthesis and antifungal activity of substituted 2,4,6-pyrimidinetrione carbaldehyde hydrazones

Opportunistic fungal infections caused by the Candida spp. are the most common human fungal infections, often resulting in severe systemic infections - a significant cause of morbidity and mortality in at-risk populations. Azole antifungals remain the mainstay of antifungal treatment for candidiasis, however development of clinical resistance to azoles by Candida spp. limits the drugs' efficacy and highlights the need for discovery of novel therapeutics. Recently, it has been reported that simple hydrazone derivatives have the capability to potentiate antifungal activities in vitro. Similarly, pyrimidinetrione analogs have long been explored by medicinal chemists as potential therapeutics, with more recent focus being on the potential for pyrimidinetrione antimicrobial activity. In this work, we present the synthesis of a class of novel hydrazone-pyrimidinetrione analogs using novel synthetic procedures. In addition, structure-activity relationship studies focusing on fungal growth inhibition were also performed against two clinically significant fungal pathogens. A number of derivatives, including phenylhydrazones of 5-acylpyrimidinetrione exhibited potent growth inhibition at or below 10 μM with minimal mammalian cell toxicity. In addition, in vitro studies aimed at defining the mechanism of action of the most active analogs provide preliminary evidence that these compound decrease energy production and fungal cell respiration, making this class of analogs promising novel therapies, as they target pathways not targeted by currently available antifungals.

5-Arylidene N,N-dimethylbarbiturates as urease inhibitors

Earlier 5-arylidene N,N-dimethylbarbiturates 1-24 were reported by our group as novel antioxidant, nevertheless, urease inhibitory activity of these compounds has not been investigated at all. In the present study, compounds 1-24 were synthesized by the reaction of N,N-dimethylbarbituric acid with different aromatic aldehydes, and screened for their in vitro urease inhibitory effects. Compound 7, was found to be most active urease inhibitor in the series. Nonetheless, compounds 11, 12, and 19 were also active against urease enzyme.