33458-27-4

Basic information

• Product Name: 5-PyriMidinecarboxylic acid, 1,2,3,4-tetrahydro-2-oxo-, ethyl ester
• Synonyms: 5-PyriMidinecarboxylic acid, 1,2,3,4-tetrahydro-2-oxo-, ethyl ester;2-Oxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid ethyl ester
• CAS NO: 33458-27-4
• Molecular Formula: C₇H₁₀N₂O₃
• Molecular Weight: 170.1659
• Mol File: 33458-27-4.mol
• Article Data: 14

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 5-PyriMidinecarboxylic acid, 1,2,3,4-tetrahydro-2-oxo-, ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 5-PyriMidinecarboxylic acid, 1,2,3,4-tetrahydro-2-oxo-, ethyl ester(33458-27-4)
• EPA Substance Registry System: 5-PyriMidinecarboxylic acid, 1,2,3,4-tetrahydro-2-oxo-, ethyl ester(33458-27-4)

Safety Data

• Hazardous Substances Data: 33458-27-4(Hazardous Substances Data)

Usage

General Description

5-Pyrimidinecarboxylic acid, 1,2,3,4-tetrahydro-2-oxo-, ethyl ester, also known as ethyl 3,4-dihydro-2-oxopyrimidine-5-carboxylate, is a chemical compound with the molecular formula C8H10N2O3. 5-PyriMidinecarboxylic acid, 1,2,3,4-tetrahydro-2-oxo-, ethyl ester is an ethyl ester derivative of 3,4-dihydro-2-oxopyrimidine-5-carboxylic acid and is commonly used as a building block in the synthesis of pharmaceuticals and agrochemicals. It is a white to off-white solid with a molecular weight of 182.17 g/mol and a melting point of 76-78°C. 5-Pyrimidinecarboxylic acid, 1,2,3,4-tetrahydro-2-oxo-, ethyl ester is a versatile intermediate in organic synthesis and has applications in the production of various chemical compounds.

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Downstream Products

• 95928-49-7 ethyl 2-oxo-1,2-dihydropyrimidine-5-carboxylate 
• 57401-76-0 2-aminopyrimidine-5-carboxylic acid ethyl ester 
• 89793-12-4 ethyl 2-chloropyrimidine-5-carboxylate 
• 304431-55-8 ethyl 2-[N-(3,5-di-tert-butylphenyl)amino] pyrimidine-5-carboxylate 
• 304431-56-9 ethyl 2-[N-(3,5-di-tert-butylphenyl)-N-methylamino] pyrimidine-5-carboxylate 
• 304431-57-0 ethyl 2-[N-ethyl-N-(3,5-di-tert-butylphenyl)amino] pyrimidine-5-carboxylate 
• 110099-99-5 2-CHLOROPYRIMIDINE-5-CARBONYLCHLORIDE 
• 1753-50-0 2-chloropyrimidine-5-carbonitrile 
• 1213234-72-0 (5-{2-[1-(3,4,5-Trichlorobenzyl)-1H-1,2,3-triazol-4-yl]pyrimidin-5-yl}-2H-tetrazol-2-yl)acetic acid 
• 856595-94-3 2-chloropyrimindine-5-carboxaminde 
• 1213234-95-7 2-[1-(3,4,5-trichlorobenzyl)-1H-1,2,3-triazol-4-yl]pyrimidine-5-carbonitrile 
• 1213234-96-8 5-(2H-tetrazol-5-yl)-2-[1-(3,4,5-trichlorobenzyl)-1H-1,2,3-triazol-4-yl]pyrimidine 
• 1213234-97-9 ethyl (5-{2-[1-(3,4,5-trichlorobenzyl)-1H-1,2,3-triazol-4-yl]pyrimidin-5-yl}-2H-tetrazol-2-yl)acetate 
• 603965-77-1 ethyl 2-(piperazin-1-yl) pyrimidine-5-carboxylate 

Relevant articles and documents

COMBINATION THERAPY WITH A PHOSPHOINOSITIDE 3-KINASE INHIBITOR WITH A ZINC BINDING MOIETY

The invention provides a method of treating cancer in a subject in need thereof, comprising administering to the subject: (a) a compound of Formula I: or a pharmaceutically acceptable salt thereof, wherein R is hydrogen or an acyl group; and (b) a PD-1 signaling inhibitor; wherein the compound of Formula I or pharmaceutically acceptable salt thereof and the PD-1 signaling inhibitor are administered in amounts which in combination are therapeutically effective. The invention further provides a pharmaceutical composition comprising a compound of Formula I or a pharmaceutically acceptable salt thereof, a PD-1 signaling inhibitor and a pharmaceutically acceptable carrier or excipient.

COMBINATION THERAPY WITH A PHOSPHOINOSITIDE 3-KINASE INHIBITOR WITH A ZINC BINDING MOIETY

The invention provides a method of treating cancer in a subject in need thereof, comprising administering to the subject: (a) a compound of Formula I: or a pharmaceutically acceptable salt thereof, wherein R is hydrogen or an acyl group; and (b) a BCL-2 inhibitor; wherein the compound of Formula I or pharmaceutically acceptable salt thereof and a BCL-2 inhibitor are administered in amounts which in combination are therapeutically effective. The invention further provides a pharmaceutical composition comprising a compound of Formula I or a pharmaceutically acceptable salt thereof, a BCL-2 inhibitor and a pharmaceutically acceptable carrier or excipient.

Design and synthesis of novel androgen receptor antagonists via molecular modeling

Several androgen receptor (AR) antagonists are clinically prescribed to treat prostate cancer. Unfortunately, many patients become resistant to the existing AR antagonists. To overcome this, a novel AR antagonist candidate called DIMN was discovered by our research group in 2013. In order to develop compounds with improved potency, we designed novel DIMN derivatives based on a docking study and substituted carbons with heteroatom moieties. Encouraging in vitro results for compounds 1b, 1c, 1e, 3c, and 4c proved that the new design was successful. Among the newly synthesized compounds, 1e exhibited the strongest inhibitory effect on LNCaP cell growth (IC50= 0.35 μM) and also acted as a competitive AR antagonist with selectivity over the estrogen receptor (ER) and the glucocorticoid receptor (GR). A docking study of compound 1e fully supported these biological results. Compound 1e is considered to be a novel, potent and AR-specific antagonist for treating prostate cancer. Thus, our study successfully applied molecular modeling and bioisosteric replacement for hit optimization. The methods here provide a guide for future development of drug candidates through structure-based drug discovery and chemical modifications.