26908-37-2

Basic information

• Product Name: 2,4,6(1H,3H,5H)-Pyrimidinetrione,5-[(2-nitrophenyl)methylene]-
• Synonyms: 2,4,6(1H,3H,5H)-Pyrimidinetrione,5-[(2-nitrophenyl)methylene]-;5-{2-nitrobenzylidene}-2,4,6(1H,3H,5H)-pyrimidinetrione
• CAS NO: 26908-37-2
• Molecular Formula: C₁₁H₇N₃O₅
• Molecular Weight: 261.19038
• Mol File: 26908-37-2.mol
• Article Data: 21

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.558g/cm³
• Refractive Index: 1.671
• CAS DataBase Reference: 2,4,6(1H,3H,5H)-Pyrimidinetrione,5-[(2-nitrophenyl)methylene]-(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4,6(1H,3H,5H)-Pyrimidinetrione,5-[(2-nitrophenyl)methylene]-(26908-37-2)
• EPA Substance Registry System: 2,4,6(1H,3H,5H)-Pyrimidinetrione,5-[(2-nitrophenyl)methylene]-(26908-37-2)

Safety Data

• Hazardous Substances Data: 26908-37-2(Hazardous Substances Data)

Usage

Pyrimidine derivative

The compound is based on a pyrimidine ring structure, which is a six-membered nitrogen-containing ring.

Nitrophenyl group attachment

The compound has a nitrophenyl group (a phenyl group with a nitro group attached) as a substituent, which can influence its reactivity and properties.

Reactivity

The presence of the nitro group makes the compound reactive, which can be useful in various chemical reactions.

Potential precursor or reagent

The compound has the potential to be used as a starting material or reagent in organic synthesis, which can lead to the development of new compounds.

Interest to researchers

The properties and uses of the compound are of interest to researchers in the fields of chemistry, biochemistry, and pharmaceuticals, due to its potential for a range of applications.

InChI:InChI=1/C11H7N3O5/c15-9-7(10(16)13-11(17)12-9)5-6-3-1-2-4-8(6)14(18)19/h1-5H,(H2,12,13,15,16,17)

Upstream product

• 67-52-7 BARBITURIC ACID 
• 552-89-6 2-nitro-benzaldehyde 

Relevant articles and documents

One pot synthesis of barbiturates on reaction of barbituric acid with aldehydes under microwave irradiation using a variety of catalysts

The condensation of barbituric acid with aldehydes under microwave irradiation in dry media has been investigated in the presence of NH 4OAc/AcOH (4/3, w/w) (41-54%), Montmorillonite K-10 (49-60%), Silica gel (52-63%), basic Al2O3 (56-67%), NaCl (57-69%), Montmorillonite KSF (62-70%), and KSF + NaCl (1:1, w/w) (70-89%).

Comparison of the efficiency of two imidazole-based dicationic ionic liquids as the catalysts in the synthesis of pyran derivatives and Knoevenagel condensations

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.

Trisubstituted barbiturates and thiobarbiturates: Synthesis and biological evaluation as xanthine oxidase inhibitors, antioxidants, antibacterial and anti-proliferative agents

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.