188781-04-6

Basic information

• Product Name: Benzenepropanoic acid, a-[[(aminocarbonyl)amino]methylene]-b-oxo-, ethyl ester
• CAS NO: 188781-04-6
• Molecular Formula: C13H14N2O4
• Molecular Weight: 262.265
• Mol File: 188781-04-6.mol

Chemical Properties

• CAS DataBase Reference: Benzenepropanoic acid, a-[[(aminocarbonyl)amino]methylene]-b-oxo-, ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenepropanoic acid, a-[[(aminocarbonyl)amino]methylene]-b-oxo-, ethyl ester(188781-04-6)
• EPA Substance Registry System: Benzenepropanoic acid, a-[[(aminocarbonyl)amino]methylene]-b-oxo-, ethyl ester(188781-04-6)

Safety Data

• Hazardous Substances Data: 188781-04-6(Hazardous Substances Data)

Upstream product

• 94-02-0 ethyl 3-oxo-3-phenylpropionate 
• 122-51-0 orthoformic acid triethyl ester 
• 57-13-6 urea 

Downstream Products

• 188781-11-5 2-chloro-4-phenylpyrimidine-5-carboxylic acid 
• 188781-14-8 2-chloro-4-phenylpyrimidine-5-carbonyl chloride 
• 188936-37-0 ethyl 2-hydrazino-4-phenylpyrimidine-5-carboxylate 
• 113271-89-9 ETHYL 2-CHLORO-4-PHENYLPYRIMIDINE-5-CARBOXYLATE 
• 188781-06-8 ethyl 2-hydroxy-4-phenylpyrimidine-5-carboxylate 

Relevant articles and documents

Inhibitors of NF-kappaB and AP-1 gene expression: SAR studies on the pyrimidine portion of 2-chloro-4-trifluoromethylpyrimidine-5-[N-(3', 5'-bis(trifluoromethyl)phenyl)carboxamide].

We investigated the structure-activity relationship studies of N-[3, 5-bis(trifluoromethyl)phenyl][2-chloro-4-(trifluoromethyl)pyrimidin-5 -yl]carboxamide (1), an inhibitor of transcription mediated by both NF-kappaB and AP-1 transcription factors, with the goal of improving its potential oral bioavailability. Compounds were examined for cell-based activity, were fit to Lipinski's rule of 5, and were examined for potential gastrointestinal permeability using the intestinal epithelial cell line, Caco-2. Selected groups were substituted at the 2-, 4-, and 5-positions of the pyrimidine ring using solution-phase combinatorial methodology. The introduction of a fluorine in the place of 2-chlorine of 1 resulted in a compound with comparable activity. However, other substitutions at the 2-position resulted in a loss of activity. The trifluoromethyl group at the 4-position could be replaced with a methyl, ethyl, chlorine, or phenyl without a substantial loss of activity. The carboxamide group at the 5-position is critical for activity. If it was moved to the 6-position, the activity was lost. The 2-methyl analogue of 1 (81) showed comparable in vitro activity and improved Caco-2 permeability compared to 1.

Structure-activity relationship studies of ethyl 2-[(3-methyl-2,5-dioxo(3-pyrrolinyl))amino]-4-(trifluoromethyl)pyrimidine- 5-carboxylate: An inhibitor of AP-1 and NF-κB mediated gene expression

Several analogues of ethyl 2-[(3-methyl-2,5-dioxo(3-pyrrolinyl))amino]-4-(trifluoromethyl)pyrimidine- 5-carboxylate (1) were synthesized and tested as inhibitors of AP-1 and NF-κB mediated transcriptional activation in Jurkat T cells. From our SAR work, ethyl 2-[(3-methyl-2,5-dioxo(3-pyrrolinyl))-N-methylamino]-4-(trifluoromethyl)- pyrimidine-5-carboxylate was identified as a novel and potent inhibitor.