141266-44-6

Basic information

• Product Name: 5-(6-Chloro-2,4-dioxo-1,3,4,10-tetrahydro-2H-9-oxa-1,3-diaza-anthracen-10-yl)-pyrimidine-2,4,6-trione
• Synonyms: 5-(6-Chloro-2,4-dioxo-1,3,4,10-tetrahydro-2H-9-oxa-1,3-diaza-anthracen-10-yl)-pyrimidine-2,4,6-trione;EM20-25;Bcl-2InhibitorIII,EM20-25
• CAS NO: 141266-44-6
• Molecular Formula: C15H9ClN4O6
• Molecular Weight: 376.70816
• Mol File: 141266-44-6.mol

Chemical Properties

• Appearance: light yellow to yellow/
• Density: 1.81±0.1 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• Solubility: DMSO: ≥5mg/mL at ~60°C
• PKA: 3.18±0.20(Predicted)
• CAS DataBase Reference: 5-(6-Chloro-2,4-dioxo-1,3,4,10-tetrahydro-2H-9-oxa-1,3-diaza-anthracen-10-yl)-pyrimidine-2,4,6-trione(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(6-Chloro-2,4-dioxo-1,3,4,10-tetrahydro-2H-9-oxa-1,3-diaza-anthracen-10-yl)-pyrimidine-2,4,6-trione(141266-44-6)
• EPA Substance Registry System: 5-(6-Chloro-2,4-dioxo-1,3,4,10-tetrahydro-2H-9-oxa-1,3-diaza-anthracen-10-yl)-pyrimidine-2,4,6-trione(141266-44-6)

Safety Data

• Hazard Codes: N
• Statements: 50
• Safety Statements: 61
• WGK Germany: 3
• Hazardous Substances Data: 141266-44-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
5-(6-Chloro-2,4-dioxo-1,3,4,10-tetrahydro-2H-9-oxa-1,3-diaza-anthracen-10-yl)-pyrimidine-2,4,6-trione is used as a potential therapeutic agent for targeting Bcl-2/BAX interactions in the pharmaceutical industry. The disruption of these interactions has been observed to induce apoptosis in tumor cells, making it a promising candidate for the development of anticancer drugs.
Used in Cancer Research:
In the field of cancer research, this compound is utilized as a tool to study the mechanisms underlying the regulation of apoptosis and the role of Bcl-2/BAX interactions in tumor cell survival. Understanding these mechanisms can lead to the development of novel targeted therapies for various types of cancer.
Used in Drug Design and Development:
5-(6-Chloro-2,4-dioxo-1,3,4,10-tetrahydro-2H-9-oxa-1,3-diaza-anthracen-10-yl)-pyrimidine-2,4,6-trione serves as a structural template for the design and development of new drugs with improved efficacy and selectivity. Its unique molecular architecture can be further modified and optimized to enhance its biological activities and pharmacological properties, potentially leading to the discovery of more effective anticancer agents.
Used in Drug Delivery Systems:
Similar to gallotannin, this compound may also benefit from the development of novel drug delivery systems to improve its bioavailability, delivery, and therapeutic outcomes. The use of organic and metallic nanoparticles as carriers can help overcome limitations associated with the compound's solubility, stability, and cellular uptake, ultimately enhancing its potential as a cancer treatment.

Upstream product

• 67-52-7 BARBITURIC ACID 
• 635-93-8 5-chlorosalicyclaldehyde 

Relevant articles and documents

Complete chemical shift assignment and molecular modeling studies of two chromene derivatives as potential leads for new anticancer drugs

The compounds 7-chloro-9-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-en-1-yl)-3,3-dimethyl-2,3,4,9-tetrahydro-1H-xanthen-1-one (5) and 5-[-7-chloro-2,4-dioxo-1H, 2H, 3H, 4H, 5H-chromeno[2,3-d]pyrimidin-5-yl)]-1,3-diazinane-2,4,6-trione (7), were synthesized from dimedone and barbituric acid and had their three-dimensional structures and precise chemical shifts assignments obtained by Nuclear Magnetic Resonance (NMR) from 1H, 13C, APT, COSY, HSQC, and HMBC spectra. Additional HOMO-LUMO DFT calculations corroborated the NMR results and pointed to the most stable stereoisomers of each compound. Besides, further docking and molecular dynamic studies suggest that the stereoisomers (9S)-7-chloro-9-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-en-1-yl)-3,3-dimethyl-2,3,4,9-tetrahydro-1H-xanthen-1-one, and 5-[(5S)-7-chloro-2,4-dioxo-1H, 2H, 3H, 4H, 5H-chromeno[2,3-d]pyrimidin-5-yl)]-1,3-diazinane-2,4,6-trione of these compounds may act as DNA intercalators and qualify as potential leads for the development of new anticancer drugs. Communicated by Ramaswamy H. Sarma.

Synthesis of oxadeazaflavines from barbituric acid and aromatic aldehydes

2H-Chromeno[2,3-d]-pyrimidine-2,4(3H)-diones were prepared directly from barbituric acid and salicylaldehydes or by thermal cyclization of the condensation product of barbituric acid and 6-bromopiperonal.

A simple approach towards the synthesis of oxadeazaflavines

The synthesis of oxadeazaflavine (2H-chromeno[2,3-d]pyrimidine-2,4(3H)-dione) derivatives (1a, 1b and 1c) from barbituric acid and salicylaldehydes as starting materials was shown to be possible using water as solvent at room temperature. The orange inter

Nuclear magnetic resonance and molecular modeling study of exocyclic carbon-carbon double bond polarization in benzylidene barbiturates

Benzylidene barbiturates are important materials for the synthesis of heterocyclic compounds with potential for the development of new drugs. The reactivity of benzylidene barbiturates is mainly controlled by their exocyclic carbon-carbon double bond. In this work, the exocyclic double bond polarization was estimated experimentally by NMR and correlated with the Hammett σ values of the aromatic ring substituents and the molecular modeling calculated atomic charge difference. It is demonstrated that carbon chemical shift differences and NBO charge differences can be used to predict their reactivity.

Synthesis and in vitro antibacterial activities of 5-(2,3,4,5-Tetrahydro- 1H-chromeno[2,3-d]pyrimidin-5-yl)pyrimidione derivatives

A series of novel 5-(2,3,4,5-tetrahydro-1H-chromeno[2,3-d]pyrimidin-5-yl) pyrimidione derivatives have been synthesized from substituted salicylaldehydes and barbituric acid or 2-thiobarbituric acid in water catalyzed by phase transfer catalysis of triethylbenzyl ammonium chloride (TEBA). Elemental analysis, IR, 1H NMR, and 13C NMR elucidated the structures of all the newly synthesized compounds. In vitro antimicrobial activities of synthesized compounds have been investigated against Escherichia coli, Bacillus subtilis, Staphylococcus aureus, and Pseudomonas aeruginosa. These newly synthesized derivatives exhibited significant in vitro antibacterial activity. A series of novel 5-(2,3,4,5-tetrahydro-1H-chromeno[2,3-d]pyrimidin- 5-yl)pyrimidione derivatives have been synthesized from substituted salicylaldehydes and barbituric acid or 2-thiobarbituric acid in water catalyzed by phase transfer catalysis of triethylbenzyl ammonium chloride (TEBA). Elemental analysis, IR, 1H NMR, and 13C NMR elucidated the structures of all the newly synthesized compounds. In vitro antimicrobial activities of synthesized compounds have been investigated against Escherichia coli, Bacillus subtilis, Staphylococcus aureus, and Pseudomonas aeruginosa. Copyright