58713-03-4

Usage

Uses

Used in Pharmaceutical Industry:
5-Acetyl-1,3-dimethylbarbituric is used as an intermediate in the synthesis of other organic compounds and pharmaceuticals for its sedative and hypnotic properties. It is utilized in the treatment of conditions such as epilepsy and insomnia due to its effects on neurotransmitter activity in the brain.
Used in Research and Development:
5-Acetyl-1,3-dimethylbarbituric is used as a research compound to study its central nervous system depressant effects and its potential for abuse and dependence. This helps in understanding the mechanisms of action and developing safer alternatives or treatments for related conditions.

InChI:InChI=1/C8H10N2O4/c1-4(11)5-6(12)9(2)8(14)10(3)7(5)13/h5H,1-3H3

Upstream product

• 769-42-6 1,3-dimethylbarbituric acid 
• 108-24-7 acetic anhydride 
• 598-94-7 1,1-Dimethylurea 
• 75-36-5 acetyl chloride 
• 64-19-7 acetic acid 

Downstream Products

• 7391-61-9 1,3-dimethyl-5-ethylpyrimidine-2,4,6-(1H,3H,5H)-trione 
• 915222-02-5 5-[1-((1R,2R)-2-Amino-cyclohexylamino)-ethylidene]-1,3-dimethyl-pyrimidine-2,4,6-trione 
• 951322-68-2 C₂₂H₂₄N₄O₃ 
• 1309596-53-9 (2E)-3-(5-chloro-3-methyl-1-phenylpyrazol-4-yl)-1-(1,3-dimethyl-2,4,6-pyrimidinetrione-5-yl)-2-propen-1-one 
• 1309596-61-9 C₁₉H₁₉ClN₆O₃ 
• 1207290-27-4 C₂₂H₂₄N₄O₃ 
• 1551642-59-1 1,3-dimethyl-5-[(1E)-N-phenylethanimidoyl]pyrimidine-2,4,6-trione 
• 1551642-33-1 5-[(1E)-N-(4-hydroxyphenyl)ethanimidoyl]-1,3-dimethylpyrimidine-2,4,6-trione 
• 1551642-76-2 5-[(1E)-N-(4-methoxyphenyl)ethanimidoyl]-1,3-dimethylpyrimidine-2,4,6-trione 
• 1551641-39-4 5-{(1E)-1-[2-(2,4-dinitrophenyl)hydrazinylidene]ethyl}-1,3-dimethylpyrimidine-2,4,6-trione 
• 951322-69-3 C₃₀H₃₀N₄O₃ 

Relevant academic research and scientific papers

5-Hydrazinylethylidenepyrimidines effective against multidrug-resistant Acinetobacter baumannii: Synthesis and in vitro biological evaluation of antibacterial, radical scavenging and cytotoxic activities

Acinetobacter baumannii has emerged as an important nosocomial pathogen in recent years, with infectious outbreaks caused by multidrug-resistant strains increasing worldwide. Thus, new antibacterial treatments for multidrug-resistant A. baumannii strains

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.

Synthesis, Characterization, and Tautomerism of 1,3-Dimethyl Pyrimidine-2,4,6-Trione s-Triazinyl Hydrazine/Hydrazone Derivatives

1,3,5-Triazines and pyrimidine-2,4,6-triones belong to that class of compounds which are well known in literature for possessing wide range of biological activities. Here, we report a new family of compounds that encompasses these two structures. The unio

Asymmetric isomerization of ω-hydroxy-α,β-unsaturated thioesters into β-mercaptolactones by a bifunctional aminothiourea catalyst

We present a novel methodology for the asymmetric synthesis of β-mercaptolactones via isomerization of ω-hydroxy-α,β- unsaturated thioesters by means of a bifunctional aminothiourea catalyst. The catalyst interacts with the substrate through the cooperati

MELDRUM 'S ACID, BARBITURIC ACID AND PYRAZOLONE DERIVATIVES SUBSTITUTED WITH HYDROXYLAMINE AS HNO DONORS

The disclosed subject matter provides certain N-substituted hydroxylamine derivative compounds, pharmaceutical compositions and kits comprising such compounds, and methods of using such compounds or pharmaceutical compositions. In particular, the disclosed subject matter provides methods of using such compounds or pharmaceutical compositions for treating, preventing, or delaying the onset and/or development of a disease or condition. In some embodiments, the disease or condition is selected from cardiovascular diseases, ischemia, reperfusion injury, cancerous disease, pulmonary hypertension and conditions responsive to nitroxyl therapy.

Thermal solvent-free synthesis of novel pyrazolyl chalcones and pyrazolines as potential antimicrobial agents

A novel approach was adopted for the synthesis of series of new pyrazolyl chalcones (3a-c) by the reaction of 5-chloro-3-methyl-1-phenylpyrazole-4- carboxaldehyde (1) with different 5-acetylbarbituric acid derivatives (2a-c) under thermal solvent-free con

A facile synthesis of 5-acylbarbituric acids under microwave irradiations

N-Monosubstituted and N,N'-disubstituted barbituric acids on treatment with benzoic anhydride/acetic anhydride under microwave irradiations without using any solvent provide a convenient methodology for the synthesis of 5-benzoyl/ acylbarbituric acids in moderate to high yields.

O-COORDINATED METAL CHELATES AND THEIR USE IN OPTICAL RECORDING MEDIA HAVING HIGH STORAGE CAPACITY

The invention relates to novel o ptical recording materials that comprise specific and in some cases novel diketone enamines or metal chelates thereof and that have excellent recording and playback quality especially ata wavelength of 350-500 nm. The invention accordingly relates to an optical recording medium comprising a substrate, a recording layer and optionally a reflecting layer, wherein the recording layer comprises a compound of formula (I), wherein M is hydrogen, aluminium or, preferably, a transition metal, which may in addition be coordinated with one or more further ligands and/or, for balancing out an excess charge, where applicable, may have an electrostatic interaction with one or more further ions inside or outside the coordination sphere, but M in formulae (Ib) and (Ic) is not hydrogen, Q is C-H, N or C-R6, it being possible for the stereochernistry of the C=Q double bond to be either E or Z. For the exact definitions of R1 to R6 reference should be made to the description. Also claimed are the novel compounds, especially tetracoordinated chelates, and a process for the preparation thereof.

Preparation of 5-formyl- and 5-acetylbarbituric acids, including the corresponding Schiff bases and phenylhydrazones

Simple, effective, and high yield synthetic procedures for formylation and acetylation of barbituric acid derivatives is described. Generated 5-acylbarbituric acids are transformed into the corresponding Schiff bases in high yield condensation reactions with ω-aminoalkanoic acids and nitrophenylhydrazines.