GSK1292263

Base Information

• Chemical Name: GSK1292263
• CAS No.: 1032823-75-8
• Molecular Formula: C23H28N4O4S
• Molecular Weight: 456.566
• Mol file: 1032823-75-8.mol

Synonyms:GSK1292263;5-[[[1-[3-(1-Methylethyl)-1,2,4-oxadiazol-5-yl]-4-piperidinyl]methyl]oxy]-2-[4-(methylsulfonyl)phenyl]pyridine;3-isopropyl-5-(4-(((6-(4-(Methylsulfonyl)phenyl)pyridin-3-yl)oxy)Methyl)piperidin-1-yl)-1,2,4-oxadiazole

Chemical Property of GSK1292263

Chemical Property:

• Boiling Point: 655.1±65.0 °C(Predicted)
• PKA: 4.75±0.32(Predicted)
• PSA: 106.80000
• Density: 1.23
• LogP: 5.09970
• Solubility.: ≥21.1 mg/mL in DMSO; insoluble in H2O; insoluble in EtOH

Purity/Quality:

99%, ^*data from raw suppliers

3-Isopropyl-5-(4-(((6-(4-(methylsulfonyl)phenyl)pyridin-3-yl)oxy)methyl)piperidin-1-yl)-1,2,4-oxadiazole 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of GSK1292263

There total 5 articles about GSK1292263 which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.5%

(1-(3-isopropyl-1,2,4-oxadiazol-5-yl)piperidin-4-yl)methanol (1032824-92-2) + 5-fluoro-2-(4-(methylsulfonyl)phenyl)pyridine → ((5-[({1-[3-(1-methylethyl)-1,2,4-oxadiazol-5-yl]-4-piperidinyl}methyl)oxy]-2-[4-(methylsulfonyl)phenyl]pyridine)) (1032823-75-8)

Guidance literature:

(1-(3-isopropyl-1,2,4-oxadiazol-5-yl)piperidin-4-yl)methanol; With potassium tert-butylate; In tetrahydrofuran; at 0 - 15 ℃; for 0.5h; Large scale;

5-fluoro-2-(4-(methylsulfonyl)phenyl)pyridine; In tetrahydrofuran; at 0 - 22 ℃; for 0.1h; Reagent/catalyst; Solvent; Large scale;

DOI:10.1021/acs.oprd.6b00157

Reference yield: 84.0%

(1-(3-isopropyl-1,2,4-oxadiazol-5-yl)piperidin-4-yl)methyl methanesulfonate (1032825-19-6) + 6-[4-(methylsulfonyl)phenyl]-3-pyridinol (1032825-20-9) → ((5-[({1-[3-(1-methylethyl)-1,2,4-oxadiazol-5-yl]-4-piperidinyl}methyl)oxy]-2-[4-(methylsulfonyl)phenyl]pyridine)) (1032823-75-8)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 80 ℃; for 20h;

Reference yield: 21.0%

→ ((5-[({1-[3-(1-methylethyl)-1,2,4-oxadiazol-5-yl]-4-piperidinyl}methyl)oxy]-2-[4-(methylsulfonyl)phenyl]pyridine)) (1032823-75-8)

Guidance literature:

upstream raw materials:

6-[4-(methylsulfonyl)phenyl]-3-pyridinol

(1-(3-isopropyl-1,2,4-oxadiazol-5-yl)piperidin-4-yl)methanol

(1-(3-isopropyl-1,2,4-oxadiazol-5-yl)piperidin-4-yl)methyl methanesulfonate

4-piperidinemethanol

Downstream raw materials:

5-[({1-[3-(1-Methylethyl)-1,2,4-oxadiazol-5-yl]-4-piperidinyl}methyl)oxy]-2-[4-(methylsulfonyl)phenyl]pyridine hydrochloride

Refernces

Discovery of the oxazabicyclo[3.3.1]nonane derivatives as potent and orally active GPR119 agonists

10.1016/j.bmcl.2015.09.047

This study focused on the design, synthesis, and evaluation of oxazolidinone bicyclo[3.3.1]nonane derivatives as GPR119 agonists for their potential antidiabetic effects. GPR119 is a receptor expressed in pancreatic β cells and intestinal enteroendocrine cells, and its agonists promote glucose-dependent insulin secretion and incretin release. The researchers explored two conformationally constrained scaffolds, B and C, to improve the solubility and efficacy of the compounds. Scaffold C with a syn configuration showed the best overall properties. Compound 25a containing scaffold C exhibited extremely potent agonist activity and significantly reduced blood glucose levels in an oral glucose tolerance test in mice at a dose of 0.1 mg/kg. The study also involved modifications to the pyrimidine core, benzene ring, and linker to optimize the properties of the compound, resulting in improved solubility and sustained plasma exposure in a pharmacokinetic assay in rats.

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