114832-72-3

Basic information

• Product Name: 2-oxo-1,2,3,6-tetrahydropyrimidine-4,6-dicarboxylate
• Synonyms: 2-oxo-1,2,3,6-tetrahydropyrimidine-4,6-dicarboxylate
• CAS NO: 114832-72-3
• Molecular Formula: C6H8 N2 O5
• Molecular Weight: 188.14
• Mol File: 114832-72-3.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 611.7°Cat760mmHg
• Flash Point: 323.7°C
• Appearance: /
• Density: 1.574g/cm³
• Vapor Pressure: 1.55E-16mmHg at 25°C
• Refractive Index: 1.539
• CAS DataBase Reference: 2-oxo-1,2,3,6-tetrahydropyrimidine-4,6-dicarboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: 2-oxo-1,2,3,6-tetrahydropyrimidine-4,6-dicarboxylate(114832-72-3)
• EPA Substance Registry System: 2-oxo-1,2,3,6-tetrahydropyrimidine-4,6-dicarboxylate(114832-72-3)

Safety Data

• Hazardous Substances Data: 114832-72-3(Hazardous Substances Data)

Usage

InChI:InChI=1/C6H8N2O5/c9-4(10)2-1-3(5(11)12)8-6(13)7-2/h2-3H,1H2,(H,9,10)(H,11,12)(H2,7,8,13)

Upstream product

• 1421-04-1 2,4-diaminopentanedioic acid 
• 114132-73-9 trans-4,6-dicarbomethoxy-3,4,5,6-tetrahydropyrimidin-2(1H)-one 
• 114132-74-0 cis-4,6-dicarbomethoxy-3,4,5,6-tetrahydropyrimidin-2(1H)-one 
• 114132-72-8 d,l-α,α'-diaminoglutaric acid dimethyl ester dihydrochloride 
• 114182-30-8 meso-α,α'-diaminoglutaric acid dimethyl ester dihydrochloride 

Relevant articles and documents

2-oxo-4-carboxy-pyrimidines and their use as anti-malaria and anti-cancer agents

A compound for use as an inhibitor for the enzyme dihydroorotase and which is of general formula (I) STR1 where either (i) A and B together are =S or (ii) A is --H, and B is --COR2 or --SR6 ; and R1 and R2 which may be the same or different are --OH; alkyloxymethyl, a di-, tri- or polypeptide group, --OR where R is saturated or unsaturated C1-16 alkyl, C1-16 alkyloxymethyl, or 4-alkyl-piperidinyl-alkyl, --NR'R' where each R' is independently selected from --H, saturated or unsaturated C1-16 alkyl, or any group above to be hydrolyzed in vivo to hydroxy; R3 and R4 which may be the same or different are --H, C1-6 alkyl, hydroxy C1-16 alkyl, hydroxy C1-6 ether group, tetrahydrofuranyl, tetrahydropyranyl, a sugar or acetylated sugar group, hexylcarbamyl, methylglycine-N-carbonyl, or any group able to be hydrolyzed in vivo to --H; R5 is --H, halo, or C1-6 alkyl; R6 is C1-6 alkyl or 1-methyl-4-nitroimidazol-5-yl; and the dotted line represents a double bond which may be absent or present in the 4-5 position. The compounds are useful as anti-cancer and anti-malarial drugs.

cis-4-Carboxy-6-(mercaptomethyl)-3,4,5,6-tetrahydropyrimidin-2(1H)-one, a Potent Inhibitor of Mammalian Dihydroorotase

A series of cis- and trans-4-carboxy-3,4,5,6-tetrahydropyrimidine-2(1H)-ones possessing either a carboxy, hydroxymethyl, or mercaptomethyl substituent at C-6 were prepared and tested for their ability to inhibit mammalian dihydroorotase.Of these compounds, only the cis-6-mercaptomethyl compound, cis-1, was found to be a potent competitive inhibitor of the enzyme (Ki = 140 nM at pH 7.4 and 8.5) when assayed in the direction of dihydro-L-orotate hydrolysis.These results suggest that the inhibition arises from the ligation of the thiolate to the zinc atom which is thought to be located in the enzyme's active site.Although analysis of cis-1 with 2,2'-dithiobis(5-nitrobenzoic acid) revealed significant loss of the free thiol group under enzymatic assay conditions, the addition of the reducing agent, dithiothreitol, to the enzymatic reaction mixtures afforded cis-1 complete protection against this chemical decomposition, as evidenced by lowering of the inhibition constant in the presence of dithiothreitol.Compound cis-1- had no significant antiproliferative activity against B16 melanoma cells in tissue culture, possibly due to the rapid decomposition of the compound or poor permeability into cells.