5759-75-1

Basic information

• Product Name: 2,4(1H,3H)-Pyrimidinedione, 6-chloro-3-phenyl-
• CAS NO: 5759-75-1
• Molecular Formula: C10H7ClN2O2
• Molecular Weight: 222.631
• Mol File: 5759-75-1.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 2,4(1H,3H)-Pyrimidinedione, 6-chloro-3-phenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4(1H,3H)-Pyrimidinedione, 6-chloro-3-phenyl-(5759-75-1)
• EPA Substance Registry System: 2,4(1H,3H)-Pyrimidinedione, 6-chloro-3-phenyl-(5759-75-1)

Safety Data

• Hazardous Substances Data: 5759-75-1(Hazardous Substances Data)

Usage

General Description

6-chloro-3-phenyl-2,4(1H,3H)-Pyrimidinedione is a chemical compound that belongs to the pyrimidine family. It is a heterocyclic organic compound with a molecular formula of C10H6ClN2O2. 2,4(1H,3H)-Pyrimidinedione, 6-chloro-3-phenyl- is a white crystalline powder that is soluble in organic solvents and has a melting point of 239-241°C. It is used as an intermediate in the synthesis of pharmaceuticals and agrochemicals, including insecticides and herbicides. Its structural and chemical properties make it useful for various applications in the pharmaceutical and agricultural industries.

Upstream product

• 15018-50-5 1-phenyl-pyrimidine-2,4,6-trione 

Downstream Products

• 144486-27-1 3-Phenyl-6-(4-methylphenylamino)uracil 
• 90995-14-5 3-Phenyl-6-(4-chlorophenylamino)uracil 
• 80947-54-2 3-Phenyl-6-phenylsulfanyl-1H-pyrimidine-2,4-dione 
• 82500-48-9 6-(4-Chloro-phenoxy)-3-phenyl-1H-pyrimidine-2,4-dione 
• 90995-13-4 3-Phenyl-6-(3,4-dimethylphenylamino)uracil 
• 7269-14-9 3-Phenyl-6-phenylaminouracil 
• 80947-55-3 6-(4-Chloro-phenylsulfanyl)-3-phenyl-1H-pyrimidine-2,4-dione 
• 302897-03-6 6-(6-hydroxyhexyl)amino-3-phenyluracil 
• 1079130-52-1 C₁₇H₁₅N₃O₃ 
• 1079130-49-6 C₁₇H₁₅N₃O₂ 
• 84459-31-4 6-Methylamino-3-phenyl-1H-pyrimidine-2,4-dione 
• 1079130-55-4 C₁₆H₁₂FN₃O₂ 
• 1448807-12-2 6-[N-[(E)-(4-ethylphenyl)methyleneamino]-N-methylamino]-3-phenyl-1H-pyrimidine-2,4-dione 
• 1448807-18-8 3-(4-ethylphenyl)-1-methyl-6-phenylpyrimido[5,4-e][1,2,4]triazine-5,7-dione 

Relevant articles and documents

Investigation of 3-aryl-pyrimido[5,4-e][1,2,4]triazine-5,7-diones as small molecule antagonists of β-catenin/TCF transcription

Nearly all colorectal cancers (CRCs) and varied subsets of other cancers have somatic mutations leading to β-catenin stabilization and increased β-catenin/TCF transcriptional activity. Inhibition of stabilized β-catenin in CRC cell lines arrests their growth and highlights the potential of this mechanism for novel cancer therapeutics. We have pursued efforts to develop small molecules that inhibit β-catenin/TCF transcriptional activity. We used xanthothricin, a known β-catenin/TCF antagonist of microbial origin, as a lead compound to synthesize related analogues with drug-like features such as low molecular weight and good metabolic stability. We studied a panel of six candidate Wnt/β-catenin/Tcf- regulated genes and found that two of them (Axin2, Lgr5) were reproducibly activated (9-10 fold) in rat intestinal epithelial cells (IEC-6) following β-catenin stabilization by Wnt-3a ligand treatment. Two previously reported β-catenin/TCF antagonists (calphostin C, xanthothricin) and XAV939 (tankyrase antagonist) inhibited Wnt-activated genes in a dose-dependent fashion. We found that four of our compounds also potently inhibited Wnt-mediated activation in the panel of target genes. We investigated the mechanism of action for one of these (8c) and demonstrated these novel small molecules inhibit β-catenin transcriptional activity by degrading β-catenin via a proteasome-dependent, but GSK3β-, APC-, AXIN2- and βTrCP-independent, pathway. The data indicate the compounds act at the level of β-catenin to inhibit Wnt/β-catenin/TCF function and highlight a robust strategy for assessing the activity of β-catenin/TCF antagonists.

ISOLATION OF NEW CHLORINATED REGIOISOMERS OF MONO N-SUBSTITUTED URACIL DERIVATIVES AND SYNTHESIS OF 3-SUBSTITUTED 8-PHENYLPYRIMIDO-1,2,4-TRIAZINE-5,7(6H,8H)-DIONES

A variety of fervenulin type products, 3-substituted 8-phenylpyrimido-1,2,4-triazine-5,7(6H,8H)-diones (18a-i), were synthesized by nitrosative or nitrative cyclization of the aldehyde hydrazones (17a-i) derived from 6-(1-methylhydrazino)-1-phenyluracil (16) with aliphatic as well as aromatic aldehydes.The compound (16) was prepared by the reaction of 6-chloro-1-phenyluracil (8) with methylhydrazine.In addition, not only the precursor of 16, 6-chloro-1-phenyluracil (8), but also other new chlorinated regioisomers of mono N-substituted pyrimidine (9) and uracil (14) were isolated and characterized by the reductive dechlorination of them.