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SML1883

Sigma-Aldrich

AR231453

≥98% (HPLC)

Sinónimos:

AR231453, (2-Fluoro-4-methanesulfonylphenyl)-(6-[4-(3-isopropyl-[1,2,4]oxadiazol-5-yl)-piperidin-1-yl]-5-nitropyrimidin-4-yl)amine, AR-231,453, N-(2-Fluoro-4-(methylsulfonyl)phenyl)-6-(4-(3-isopropyl-1,2,4-oxadiazol-5-yl)piperidin-1-yl)-5-nitropyrimidin-4-amine

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About This Item

Fórmula empírica (notación de Hill):
C21H24FN7O5S
Número de CAS:
733750-99-7
Peso molecular:
505.52
MDL number:
MFCD14706714
UNSPSC Code:
12352200
NACRES:
NA.77

Quality Level

100

assay

≥98% (HPLC)

form

powder

storage condition

desiccated

color

white to beige

solubility

DMSO: 20 mg/mL, clear

storage temp.

−20°C

SMILES string

CC(C)C1=NOC(C(CC2)CCN2C(N=CN=C3NC4=CC=C(C=C4F)S(=O)(C)=O)=C3[N+]([O-])=O)=N1

InChI

1S/C21H24FN7O5S/c1-12(2)18-26-21(34-27-18)13-6-8-28(9-7-13)20-17(29(30)31)19(23-11-24-20)25-16-5-4-14(10-15(16)22)35(3,32)33/h4-5,10-13H,6-9H2,1-3H3,(H,23,24,25)

InChI key

DGBKNTVAKIFYNU-UHFFFAOYSA-N

Biochem/physiol Actions

AR231453 is a 5-nitropyrimidine derivative that acts as a highly potent and selective GPR119 agonist (EC50/GPR119 species = 0.4 nM/monkey, 1.6 nM/dog, 4.7 nM/hamster, 3.5 nM/human, 12 nM/mouse, 4 nM/rat in cell-based assays), exhibiting no off-target activity toward 216 receptors, enzymes, and orphan GPCRs. AR231453 improves glucose tolerance in mice (3 mg/kg i.p. or 20 mg/kg, p.o.) and rats (3 mg/kg i.p.), while no in vivo efficacy is observed among GPR119-deficient mice.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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Zhi-Liang Chu et al.
Endocrinology, 148(6), 2601-2609 (2007-02-10)
Pancreatic beta-cell dysfunction is a hallmark event in the pathogenesis of type 2 diabetes. Injectable peptide agonists of the glucagon-like peptide 1 (GLP-1) receptor have shown significant promise as antidiabetic agents by virtue of their ability to amplify glucose-dependent insulin
Graeme Semple et al.
Journal of medicinal chemistry, 51(17), 5172-5175 (2008-08-14)
GPR119 is a rhodopsin-like GPCR expressed in pancreatic beta-cells and incretin releasing cells in the GI tract. As with incretins, GPR119 increases cAMP levels in these cell types, thus making it a highly attractive potential target for the treatment of
Christoffer Norn et al.
Structure (London, England : 1993), 23(12), 2377-2386 (2015-11-04)
Recent benchmark studies have demonstrated the difficulties in obtaining accurate predictions of ligand binding conformations to comparative models of G-protein-coupled receptors. We have developed a data-driven optimization protocol, which integrates mutational data and structural information from multiple X-ray receptor structures
Deborah A Goldspink et al.
Cell reports, 31(13), 107833-107833 (2020-07-02)
Glucagon-like peptide-1 (GLP-1) from intestinal L-cells stimulates insulin secretion and reduces appetite after food ingestion, and it is the basis for drugs against type-2 diabetes and obesity. Drugs targeting L- and other enteroendocrine cells are under development, with the aim

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