53680-90-3

Basic information

• Product Name: 6-CHLORO-3-METHYL-1-PHENYL-1H-PYRIMIDINE-2,4-DIONE
• Synonyms: 6-CHLORO-3-METHYL-1-PHENYL-1H-PYRIMIDINE-2,4-DIONE
• CAS NO: 53680-90-3
• Molecular Formula: C₁₁H₉ClN₂O₂
• Molecular Weight: 236.65436
• Mol File: 53680-90-3.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 6-CHLORO-3-METHYL-1-PHENYL-1H-PYRIMIDINE-2,4-DIONE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-CHLORO-3-METHYL-1-PHENYL-1H-PYRIMIDINE-2,4-DIONE(53680-90-3)
• EPA Substance Registry System: 6-CHLORO-3-METHYL-1-PHENYL-1H-PYRIMIDINE-2,4-DIONE(53680-90-3)

Safety Data

• Hazardous Substances Data: 53680-90-3(Hazardous Substances Data)

Usage

General Description

6-CHLORO-3-METHYL-1-PHENYL-1H-PYRIMIDINE-2,4-DIONE, also known as chlormidone, is a chemical compound with the molecular formula C11H9ClN2O2. It is a pyrimidinedione derivative that is commonly used as a diuretic medication to treat edema and high blood pressure. Chlormidone works by increasing the amount of water and salt expelled from the body, which helps to decrease swelling and lower blood pressure. It is often prescribed for individuals who are unable to tolerate other diuretics or who have conditions such as congestive heart failure. Chlormidone may also have potential applications in other areas of medicine, such as in the treatment of hypertension and kidney disorders.

Upstream product

• 53727-29-0 1-phenyl-3-methyl-barbituric acid 
• 42212-19-1 6-amino-3-methyl-1-phenylpyrimidine-2,4(1H,3H)dione 
• 72702-74-0 N-cyanoacetyl-N-methyl-N'-phenyl-urea 
• 1007-36-9 1-methyl-3-phenylurea 
• 77-78-1 dimethyl sulfate 
• 155700-29-1 6-chloro-1-phenylpyrimidine-2,4(1H,3H)-dione 
• 15018-50-5 1-phenyl-pyrimidine-2,4,6-trione 

Downstream Products

• 146723-69-5 3-methyl-6-methylamino-1-phenyluracil 
• 176379-59-2 5-amino-3-methyl-6-methylamino-1-phenyluracil 
• 176378-93-1 acetic acid 3-acetoxy-5-(3-methyl-6-methylamino-2,4-dioxo-1-phenyl-1,2,3,4-tetrahydro-pyrimidin-5-ylcarbamoyl)-phenyl ester 
• 53681-14-4 3-methyl-6-(1-methylhydrazinyl)-1-phenylpyrimidine-2,4(1H,3H)-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.

Synthesis and biological evaluation of CX-659S and its related compounds for their inhibitory effects on the delayed-type hypersensitivity reaction

In order to find novel nonsteroidal compounds possessing an inhibitory activity against delayed-type hypersensitivity (DTH) reactions, we conducted random screening using a picryl chloride (PC)-induced contact hypersensitivity reaction (CHR) in mice, and found compound 1 as a lead compound. Then we synthesized and evaluated an extensive series of 5-carboxamidouracil derivatives focused on both the uracil and the antioxidative moieties. Among them, we found that the hindered phenol moiety was necessary to exhibit the activities; especially, compounds 28a-28c having the partial structure of vitamin E were found to exert potent activities against the DTH reaction by both oral and topical administration. And compound 28c showed antioxidative activity against lipid peroxidation with an IC50 of 5.9μM. Compound 28c (CX-659S) was chosen as a candidate drug for the treatment of cutaneous disorders such as atopic dermatitis and allergic contact dermatitis. Copyright (C) 2000 Elsevier Science Ltd.