Gliquidone

Base Information

• Chemical Name: Gliquidone
• CAS No.: 33342-05-1
• Molecular Formula: C27H33N3O6S
• Molecular Weight: 527.642
• Hs Code.: 29147000
• European Community (EC) Number: 251-463-2
• UNII: C7C2QDD75P
• DSSTox Substance ID: DTXSID4023096
• Nikkaji Number: J19.880C
• Wikipedia: Gliquidone
• Wikidata: Q5569924
• NCI Thesaurus Code: C72798
• Pharos Ligand ID: TZSRRWQZD37M
• Metabolomics Workbench ID: 43458
• ChEMBL ID: CHEMBL383634
• Mol file: 33342-05-1.mol

Synonyms:AR-DF 26;Beglynor;Beglynora;glikvidon;gliquidone;gliquidone, calcium salt;gliquidone, monosodium salt;Glurenor;Glurenorm;glycvidon

Chemical Property of Gliquidone

Chemical Property:

• Appearance/Colour: white powder
• Melting Point: 179 °C
• Refractive Index: 1.624
• PKA: 5.12±0.10(Predicted)
• PSA: 130.26000
• Density: 1.34 g/cm³
• LogP: 5.31900
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility.: ≥22.4 mg/mL in DMSO; insoluble in H2O; ≥2.455 mg/mL in EtOH with gentle warming and ultrasonic
• XLogP3: 4.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 7
• Exact Mass: 527.20900695
• Heavy Atom Count: 37
• Complexity: 948

Purity/Quality:

99% ^*data from raw suppliers

Gliquidone ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(C2=C(C=C(C=C2)OC)C(=O)N(C1=O)CCC3=CC=C(C=C3)S(=O)(=O)NC(=O)NC4CCCCC4)C
• Uses: It is a kind of hypoglycemic agents and can be used for the treatment of non-insulin-dependent diabetes. Gliquidone is an anti diabetic agent used in the treatment of hypoglycemia which leads to an increased risk in diabetic cardiovascular disease. Also used in the treatment diabetic nephropathy.
• Description: Gliquidone is a second generation sulfonylurea that selectively inhibits ATP-sensitive potassium channel currents (IKATP) in pancreatic β-cells (IC50s = 0.45, 119.1, and 149.7 μM for HIT-T15 cells, cardiomyocytes, and vascular smooth muscle cells, respectively). It is also a peroxisome proliferator-activated receptor γ (PPARγ) agonist (EC50 = 10 μM in a transactivation assay). Gliquidone (0.2 nmol/g) decreases plasma levels of D-glucose and stimulates insulin release in anesthetized rats. It decreases blood glucose levels, serum alkaline phosphatase (ALP), aspartate aminotransferase (AST), and alanine aminotransferase (ALT) activities, and hepatic lipid peroxidation and increases hepatic glutathione (GSH) levels in a rat model of diabetes induced by streptozotocin (STZ; ) when administered at a dose of 10 mg/kg.
• Therapeutic Function: Oral hypoglycemic

Technology Process of Gliquidone

There total 11 articles about Gliquidone 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: 98.7%

→ `Diazinon` (333-41-5,65863-03-8)

Guidance literature:

Reference yield: 98.4%

sodium 2-isopropyl-6-methylpyrimidin-4-olate (63202-32-4) + diethyl phosphorochloridothioate (2524-04-1) → `Diazinon` (333-41-5,65863-03-8)

Guidance literature:

With dmap; N-benzyl-N,N,N-triethylammonium chloride; sodium dodecyl sulfate; potassium carbonate; In water; at 50 ℃; for 2.5h; pH=9.5 - 10;

DOI:10.1080/10426507.2012.702824

Reference yield: 87.3%

→ 6,6'-diazido-6,6'-dideoxy-1',2,3,3',4,4'-hexa-O-methylsucrose + `Diazinon` (333-41-5,65863-03-8)

Guidance literature:

upstream raw materials:

4-<2-(3,4-Dihydro-7-methoxy-4,4-dimethyl-1,3-dioxo-2(1H)-isochinolyl)ethyl>benzolsulfonamid

Cyclohexyl isocyanate

diethyl phosphorochloridothioate

sodium 2-isopropyl-6-methylpyrimidin-4-olate

Downstream raw materials:

4-<2-(3,4-Dihydro-7-methoxy-4,4-dimethyl-1,3-dioxo-2(1H)-isochinolyl)ethyl>benzolsulfonamid

N-cyclohexylphthalimide

Refernces

• 1、 Ge, Xin,Qian, Chao,Chen, Xinzhi. "Investigation on the acylation of heterocyclic alcoholate anions with O,O-dialkyl phosphorochloridothioate in water solvent". supporting information. p. 739 - 744. Retrieved 2013/07/25.
• 2、 -. "NOVEL MULTIMERIC MOLECULES, A PROCESS FOR PREPARING THE SAME AND THE USE THEREOF FOR MANUFACTURING MEDICINAL DRUGS". . . Retrieved 2010/06/16.