219311-20-3

Basic information

• Product Name: 2,4,6(1H,3H,5H)-Pyrimidinetrione, 5-(4-phenoxyphenyl)-
• CAS NO: 219311-20-3
• Molecular Formula: C16H12N2O4
• Molecular Weight: 296.282
• Mol File: 219311-20-3.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: 2,4,6(1H,3H,5H)-Pyrimidinetrione, 5-(4-phenoxyphenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4,6(1H,3H,5H)-Pyrimidinetrione, 5-(4-phenoxyphenyl)-(219311-20-3)
• EPA Substance Registry System: 2,4,6(1H,3H,5H)-Pyrimidinetrione, 5-(4-phenoxyphenyl)-(219311-20-3)

Safety Data

• Hazardous Substances Data: 219311-20-3(Hazardous Substances Data)

Upstream product

• 101-55-3 4-Bromodiphenyl ether 
• 13195-64-7 diisopropyl malonate 
• 57-13-6 urea 
• 4664-61-3 methyl [p-(phenoxy)phenyl]acetate 
• 14199-15-6 Methyl 4-hydroxyphenylacetate 
• 98-80-6 phenylboronic acid 
• 288103-00-4 dimethyl 2-(4-phenoxyphenyl)malonate 
• 14062-26-1 ethyl 2-(4-phenoxyphenyl)acetate 

Downstream Products

• 467468-18-4 5-(4-phenoxyphenyl)-5-(piperazin-1-yl)pyrimidine-2,4,6 (1H,3H,5H)-trione 
• 467468-09-3 5-(4-(2(-2-hydroxyethoxy)ethyl)piperazin-1-yl)-5-(4-phenoxyphenyl)pyrimidine-2,4,6(1H,3H,5H)-trione 
• 1333167-64-8 5-(4-((tetrahydrofuran-2-yl)methyl)piperazin-1-yl)-5-(4-phenoxyphenyl)pyrimidine-2,4,6(1H,3H,5H)-trione 
• 1333167-65-9 5-(4-benzylpiperazin-1-yl)-5-(4-phenoxyphenyl)pyrimidine-2,4,6(1H,3H,5H)-trione 
• 1333167-66-0 5-(4-butylpiperazin-1-yl)-5-(4-phenoxyphenyl)pyrimidine-2,4,6(1H,3H,5H)-trione 
• 1333167-67-1 5-(4-acetylpiperazin-1-yl)-5-(4-phenoxyphenyl)pyrimidine-2,4,6(1H,3H,5H)-trione 
• 1333167-68-2 5-(4-methylpiperazin-1-yl)-5-(4-phenoxyphenyl)pyrimidine-2,4,6(1H,3H,5H)-trione 
• 1333167-78-4 5-(4-phenoxyphenyl)-5-(4-(4-cyanobenzoyl)-1,4-diazepan-1-yl)pyrimidine-2,4,6(1H,3H,5H)-trione 
• 1333167-79-5 5-(4-phenoxyphenyl)-5-(4-(6-chloropyridine-3-carbonyl)-1,4-diazepan-1-yl)pyrimidine-2,4,6(1H,3H,5H)-trione 
• 1333167-27-3 5-(4-phenoxyphenyl)-5-(4-(cyclobutanecarbonyl)-1,4-diazepan-1-yl)pyrimidine-2,4,6(1H,3H,5H)-trione 
• 1333167-28-4 5-(4-phenoxyphenyl)-5-(4-(2-(phenylthio)acetyl)-1,4-diazepan-1-yl)pyrimidine-2,4,6(1H,3H,5H)-trione 
• 1333167-29-5 5-(4-phenoxyphenyl)-5-(4-(3,5-diethoxybenzoyl)-1,4-diazepan-1-yl)pyrimidine-2,4,6(1H,3H,5H)-trione 
• 1333167-30-8 5-(4-phenoxyphenyl)-5-(4-(4-(trifluoromethoxy)benzoyl)-1,4-diazepan-1-yl)pyrimidine-2,4,6(1H,3H,5H)-trione 
• 1333167-31-9 5-(4-phenoxyphenyl)-5-(4-(3-cyclopentylpropanoyl)-1,4-diazepan-1-yl)pyrimidine-2,4,6(1H,3H,5H)-trione 

Relevant articles and documents

N-Substituted homopiperazine barbiturates as gelatinase inhibitors

Matrix metalloproteinases are implicated in a wide range of pathophysiological processes and potent selective inhibitors for these enzymes continue to be eagerly sought. 5,5-Disubstituted barbiturates hold promise as inhibitor types being stable in vivo and relatively selective for the gelatinases (MMP-2 and MMP-9). In this paper we describe the synthesis of 5-piperazine and -homopiperazine substituted barbiturates. The activity of these compounds as gelatinase inhibitors was evaluated using supernatants from 12-O-tetradecanoylphorbol-13-acetate (PMA)-stimulated HT-1080 cells as well as using recombinant human MMPs. N-Acyl homopiperazine compounds were found to be potent inhibitors of the gelatinases (range in nM) and generally more potent than the corresponding piperazine analogues. The panel of N-acyl homopiperazines was enlarged in order to exploit differences between the gelatinases at the S2′ site in order to design MMP-2- or MMP-9-selective inhibitors. Compounds in this group exhibited single digit nano-molar potency and some selectivity between the two enzymes. Representative potent compounds were effective inhibitors of cancer cell migration.

Barbituric acid derivatives with antimetastatic and antitumor activity

The invention is directed to barbituric acid derivatives having inhibitory activity for matrix maetalloproteases comprised of formula (I): pharmaceutical compositions thereof, processes for preparing the derivatives, and methods for treating diseases associated with elevated or uncontrolled levels of matrix metalloprotease activity, e.g., cancer, specifically tumor progression and tumor metastasis, inflammation, or as a method of contraception.

Pyrimidine-2,4,6-triones

A compound of formula I wherein R1is hydrogen, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, alkoxy, substituted alkoxy, aryloxy or alkylalkoxy, and R2is aryloxy, or a pharmaceutically acceptab