58713-03-4

Basic information

• Product Name: 5-Acetyl-1,3-dimethylbarbituric
• Synonyms: 5-Acetyl-1,3-dimethylbarbituric;5-Acetyl-1,3-diMethylbarbituric Acid;5-acetyl-1,3-dimethyl-1,3-diazinane-2,4,6-trione
• CAS NO: 58713-03-4
• Molecular Formula: C₈H₁₀N₂O₄
• Molecular Weight: 198.176
• Mol File: 58713-03-4.mol
• Article Data: 9

Chemical Properties

• Melting Point: 99 °C
• Boiling Point: 305.7°Cat760mmHg
• Flash Point: 135.9°C
• Appearance: /
• Density: 1.327g/cm³
• Vapor Pressure: 0.000806mmHg at 25°C
• Refractive Index: 1.509
• Storage Temp.: -20°C Freezer
• Solubility: Acetonitrile (Slightly), Chloroform (Slightly), DMSO (Slightly)
• CAS DataBase Reference: 5-Acetyl-1,3-dimethylbarbituric(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Acetyl-1,3-dimethylbarbituric(58713-03-4)
• EPA Substance Registry System: 5-Acetyl-1,3-dimethylbarbituric(58713-03-4)

Safety Data

• Hazardous Substances Data: 58713-03-4(Hazardous Substances Data)

Usage

General Description

5-Acetyl-1,3-dimethylbarbituric is a chemical compound with the molecular formula C8H12N2O3. It is a derivative of barbituric acid with an acetyl group attached to the 5th position and methyl groups attached to the 1st and 3rd positions of the barbituric acid ring. 5-Acetyl-1,3-dimethylbarbituric is used in the synthesis of other organic compounds and pharmaceuticals. It has sedative and hypnotic properties and has been used in the treatment of conditions such as epilepsy and insomnia. It is considered to be a central nervous system depressant and can have effects on neurotransmitter activity in the brain. The compound is regulated and its use is restricted in many countries due to its potential for abuse and dependence.

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

Upstream product

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

Downstream Products

• 7391-61-9 1,3-dimethyl-5-ethylpyrimidine-2,4,6-(1H,3H,5H)-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 
• 1352143-58-8 C₂₈H₃₂N₄O₃ 
• 1637484-93-5 1',1-phenyl-5',5-(1,4-phenylene)bis(3-(1,3-dimethyl-2,4,6-pyrimidinetrione-5-yl))pyrazoline 

Relevant articles and documents

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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.

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