288103-00-4

Upstream product

• 4664-61-3 methyl [p-(phenoxy)phenyl]acetate 
• 616-38-6 carbonic acid dimethyl ester 
• 101-55-3 4-Bromodiphenyl ether 
• 108-59-8 malonic acid dimethyl ester 
• 98-80-6 phenylboronic acid 
• 14199-15-6 Methyl 4-hydroxyphenylacetate 

Downstream Products

• 219311-20-3 5-(4-phenoxyphenyl)pyrimidine-2,4,6-trione 
• 288103-01-5 dimethyl 2-(4-phenoxyphenyl)-2-n-hexylmalonate 
• 1333167-63-7 5-(4-(cyclopropylcarbonyl)piperazin-1-yl)-5-(4-phenoxyphenyl)pyrimidine-2,4,6(1H,3H,5H)-trione 
• 1333167-62-6 5-(4-(cyclopropylmethyl)piperazin-1-yl)-5-(4-phenoxyphenyl)pyrimidine-2,4,6(1H,3H,5H)-trione 
• 1333167-61-5 5-(4-isopropylpiperazin-1-yl)-5-(4-phenoxyphenyl)pyrimidine-2,4,6(1H,3H,5H)-trione 
• 1333167-60-4 5-(4-cyclohexylpiperazin-1-yl)-5-(4-phenoxyphenyl)pyrimidine-2,4,6(1H,3H,5H)-trione 
• 1333167-52-4 5-(4-phenoxyphenyl)-5-(4-(1-methyl-1H-indazole-3-carbonyl)-1,4-diazepan-1-yl)pyrimidine-2,4,6(1H,3H,5H)-trione 
• 1333167-44-4 5-(4-phenoxyphenyl)-5-(4-(2,6-dichlorobenzoyl)-1,4-diazepan-1-yl)pyrimidine-2,4,6(1H,3H,5H)-trione 
• 1333167-43-3 5-(4-phenoxyphenyl)-5-(4-(4-bromobenzoyl)-1,4-diazepan-1-yl)pyrimidine-2,4,6(1H,3H,5H)-trione 
• 1333167-42-2 5-(4-phenoxyphenyl)-5-(4-(4-methylbenzoyl)-1,4-diazepan-1-yl)pyrimidine-2,4,6(1H,3H,5H)-trione 
• 1333167-41-1 5-(4-phenoxyphenyl)-5-(4-(6-(trifluoromethyl)nicotinoyl)-1,4-diazepan-1-yl)pyrimidine-2,4,6(1H,3H,5H)-trione 
• 1333167-40-0 2-(4-(2,4,6-trioxo-5-(4-phenoxyphenyl)hexahydropyrimidin-5-yl)-1,4-diazepane-1-carbonyl)benzyl benzoate 
• 1333167-39-7 5-(4-phenoxyphenyl)-5-(4-(2-(thiophen-2-yl)acetyl)-1,4-diazepan-1-yl)pyrimidine-2,4,6(1H,3H,5H)-trione 
• 1333167-38-6 5-(4-phenoxyphenyl)-5-(4-(quinoxaline-2-carbonyl)-1,4-diazepan-1-yl)pyrimidine-2,4,6(1H,3H,5H)-trione 

Relevant academic research and scientific papers

Palladium-catalyzed arylation of diisopropyl malonate applied to the efficient synthesis of the selective MMP inhibitor 5-(4-phenoxyphenyl)-5-[4-(2-pyrimidinyl)-1-piperazinyl]barbituric acid

An efficient synthesis of the highly selective MMP inhibitor 5-(4-phenoxyphenyl)-5-[4-(2-pyrimidinyl)-1-piperazinyl]barbituric acid is reported. The title compound was prepared in three steps and 72% overall yield from 4-bromophenyl phenyl ether via an im

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.

Novel 5,5-disubstitutedpyrimidine-2,4,6-triones as selective MMP inhibitors

The 5,5-disubstitutedpyrimidine-2,4,6-triones represent a new class of MMP inhibitors showing selectivity for the gelatinases A and B, collagenase-3, and human neutrophil collagenase. The SAR presented here is in good agreement with an X-ray structure of compound 5 bound to the catalytic domain of stromelysin-1. While of the barbiturate structural class, compound 5 did not show any toxic or sedative effects.

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