391249-34-6

Basic information

• Product Name: ethyl 4-[[2-(acetylamino)-5-nitro-6-oxo-1,6-dihydro-4-pyrimidinyl]amino]benzoate
• Synonyms: ethyl 4-[[2-(acetylamino)-5-nitro-6-oxo-1,6-dihydro-4-pyrimidinyl]amino]benzoate
• CAS NO: 391249-34-6
• Molecular Weight: 361.314
• Mol File: 391249-34-6.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: ethyl 4-[[2-(acetylamino)-5-nitro-6-oxo-1,6-dihydro-4-pyrimidinyl]amino]benzoate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 4-[[2-(acetylamino)-5-nitro-6-oxo-1,6-dihydro-4-pyrimidinyl]amino]benzoate(391249-34-6)
• EPA Substance Registry System: ethyl 4-[[2-(acetylamino)-5-nitro-6-oxo-1,6-dihydro-4-pyrimidinyl]amino]benzoate(391249-34-6)

Safety Data

• Hazardous Substances Data: 391249-34-6(Hazardous Substances Data)

Upstream product

• 94-09-7 p-aminoethylbenzoate 
• 51471-45-5 N₁-(6-chloro-3,4-dihydro-5-nitro-4-oxopyrimidine-2-yl)acetamide 

Downstream Products

• 391249-40-4 ethyl 4-[6-amino-8-(3-fluorophenyl)-2-[2-(1-hydroxycyclohexyl)-1-ethynyl]-9H-9-purinyl]benzoate 
• 391249-41-5 4-[6-amino-8-(3-fluorophenyl)-2-[2-(1-hydroxycyclohexyl)-1-ethynyl]-9H-9-purinyl]benzoic acid 
• 391249-39-1 ethyl 4-[6-chloro-8-(3-fluorophenyl)-2-[2-(1-hydroxycyclohexyl)-1-ethynyl]-9H-9-purinyl]benzoate 
• 391249-38-0 ethyl 4-[6-chloro-8-(3-fluorophenyl)-2-iodo-9H-9-purinyl]benzoate 
• 391249-37-9 ethyl 4-[2-amino-6-chloro-8-(3-fluorophenyl)-9H-9-purinyl]benzoate 
• 391249-36-8 ethyl 4-[(2,5-diamino-6-chloro-4-pyrimidinyl)amino]benzoate 
• 391249-35-7 ethyl 4-[(2-amino-6-chloro-5-nitro-4-pyrimidinyl)amino]benzoate 

Relevant articles and documents

2-Alkynyl-8-aryladenines possessing an amide moiety: Their synthesis and structure-activity relationships of effects on hepatic glucose production induced via agonism of the A2B adenosine receptor

A series of 2-alkynyl-8-aryladenine derivatives bearing an amide moiety at the 9-position of adenine was synthesized. These analogues were evaluated for inhibitory activity on N-ethylcarboxamidoadenosine (NECA)-induced glucose production in primary cultured rat hepatocytes. The m-primary benzamide derivative 15f was the most potent compound (IC50 = 0.017 μM), being 15-fold more active than the corresponding 9-methyl derivative (1). Compound 15f showed 72- and 5.2-fold selectivity for human A2B receptor versus human A1 and A2A receptors, respectively. Structure-activity relationship (SAR) studies of the synthesized compounds indicated that a three-carbon linker, fixed in the form of a benzene ring, between the adenine core and the amide moiety is important for both A2B antagonistic activity and selectivity. The IC50 values in rat hepatocyte glucose assay correlated well with the IC50 values in cAMP assay using Chinese hamster ovary cells stably transfected with human A2B receptors (r2 = 0.94). The A1 and A2A affinities showed no correlation with the potency to inhibit NECA-induced glucose production. These results strongly support our previous conclusion that adenosine agonist-induced hepatic glucose production in rat hepatocytes is mediated through the A2B receptor.