55427-33-3

Usage

Chemical Family

Pyrimidine-2,4,6-trione

Formation

Condensation of benzaldehyde with urea in the presence of concentrated sulfuric acid

Biological Activities

a. Antioxidant
b. Anti-inflammatory
c. Anti-cancer

Therapeutic Applications

Potential treatment for various diseases and disorders

Research Significance

Key molecule for further research and development in medicinal chemistry and drug discovery

Chemical Structure

1,3-dibenzylpyrimidine-2,4,6(1H,3H,5H)-trione

Reactivity

Influenced by its chemical structure and functional groups

Molecular Weight

Approximately 290.3 g/mol

Appearance

Likely a solid or crystalline compound, based on its molecular weight and structure

Solubility

Solvent compatibility depends on the specific functional groups and molecular structure, but generally soluble in organic solvents like methanol, ethanol, or dimethyl sulfoxide (DMSO)

Stability

Stability can vary depending on environmental factors such as temperature, light, and humidity; typically stable under controlled laboratory conditions

Synthesis

The synthesis process involves the condensation of benzaldehyde and urea, which requires specific reaction conditions and purification techniques to obtain the desired product

Analytical Techniques

Techniques such as nuclear magnetic resonance (NMR), mass spectrometry (MS), and infrared (IR) spectroscopy can be used to analyze and confirm the structure of 1,3-dibenzylpyrimidine-2,4,6(1H,3H,5H)-trione

Safety Precautions

As with any chemical compound, appropriate safety measures should be taken when handling 1,3-dibenzylpyrimidine-2,4,6(1H,3H,5H)-trione, including the use of personal protective equipment (PPE) and proper disposal methods.

Upstream product

• 597-55-7 dibenzylmalonic acid diethyl ester 
• 141-52-6 sodium ethanolate 
• 57-13-6 urea 
• 141-82-2 malonic acid 
• 1466-67-7 1,3-dibenzylurea 
• 100-46-9 benzylamine 

Downstream Products

• 102747-81-9 5,5-diallyl-1,3-dibenzyl-pyrimidine-2,4,6-trione 
• 1675821-32-5 1,3-dibenzyl-5-(2,6-dimethyl-4-hydroxybenzylidene)pyrimidine-2,4,6(1H,3H,5H)-trione 

Relevant academic research and scientific papers

Development of a One-Pot Four C-C Bond-Forming Sequence Based on Palladium/Ruthenium Tandem Catalysis

A one-pot four C-C bond-forming sequence has been developed using two distinct transition metal complexes. The sequence entails a double Pd-catalyzed allylic alkylation followed by a Ru-catalyzed ring-closing metathesis and a Pd-catalyzed Heck coupling. The use of various active methylene nucleophiles was examined with yields up to 76% (93% per C-C bond).

A novel cell-permeable, selective, and noncompetitive inhibitor of KAT3 histone acetyltransferases from a combined molecular pruning/classical isosterism approach

Selective inhibitors of the two paralogue KAT3 acetyltransferases (CBP and p300) may serve not only as precious chemical tools to investigate the role of these enzymes in physiopathological mechanisms but also as lead structures for the development of further antitumor agents. After the application of a molecular pruning approach to the hardly optimizable and not very cell-permeable garcinol core structure, we prepared many analogues that were screened for their inhibitory effects using biochemical and biophysical (SPR) assays. Further optimization led to the discovery of the benzylidenebarbituric acid derivative 7h (EML425) as a potent and selective reversible inhibitor of CBP/p300, noncompetitive versus both acetyl-CoA and a histone H3 peptide, and endowed with good cell permeability. Furthermore, in human leukemia U937 cells, it induced a marked and time-dependent reduction in the acetylation of lysine H4K5 and H3K9, a marked arrest in the G0/G1 phase and a significant increase in the hypodiploid nuclei percentage.

Pyrimidine-2,4,6-trione derivatives and their inhibition of mutant SOD1-dependent protein aggregation. Toward a treatment for amyotrophic lateral sclerosis

Amyotrophic lateral sclerosis (ALS) is a fatal neurodegenerative disease characterized by the progressive loss of motor neurons, leading to muscle weakness, paralysis, and death, most often from respiratory failure. The only FDA-approved drug for the treatment of ALS, riluzole, only extends the median survival in patients by 2-3 months. There is an urgent need for novel therapeutic strategies for this devastating disease. Using a high-throughput screening assay targeting an ALS cultured cell model (PC12-G93A-YFP cell line), we previously identified three chemotypes that were neuroprotective. We present a further detailed analysis of one promising scaffold from that group, pyrimidine-2,4,6-triones (PYTs), characterizing a number of PYT analogues using SAR and ADME. The PYT compounds show good potency, superior ADME data, low toxicity, brain penetration, and excellent oral bioavailability. Compounds from this series show 100% efficacy in the protection assay with a good correlation in activity between the protection and protein aggregation assays. The modifications of the PYT scaffold presented here suggest that this chemical structure may be a novel drug candidate scaffold for use in clinical trials in ALS.

Barbituric acid derivative and preventive and therapeutic agent for bone and cartilage containing the same

A compound of the formula wherein the substituents are as defined in the specification and solvates and salts thereof useful for treating bone and cartilage diseases.

N,N-Dialkylalloxans - a new class of catalyst for dioxirane epoxidations

N,N-Dimethyl- and N,N-dibenzylalloxans 1a and 1b have been prepared and used as novel dioxirane catalysts for the epoxidation of a range of di- and tri-substituted alkenes in good to excellent yield. The dibenzylalloxan 1b can be recovered in high yield with no evidence of catalyst decomposition.