252950-15-5

Basic information

• Product Name: (2Z)-1-(2,4-Dichlorophenyl)-3-(dimethylamino)-2-(1H-imidazol-2-yl)-2-propen-1-one
• Synonyms: (2Z)-1-(2,4-Dichlorophenyl)-3-(dimethylamino)-2-(1H-imidazol-2-yl)-2-propen-1-one
• CAS NO: 252950-15-5
• Molecular Formula: C14H13Cl2N3O
• Molecular Weight: 310.17852
• Product Categories: Amines;Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 252950-15-5.mol

Chemical Properties

• Boiling Point: 482.9±55.0 °C(Predicted)
• Appearance: /
• Density: 1.355±0.06 g/cm3(Predicted)
• Solubility: Chloroform, Methanol
• PKA: 12.35±0.10(Predicted)
• CAS DataBase Reference: (2Z)-1-(2,4-Dichlorophenyl)-3-(dimethylamino)-2-(1H-imidazol-2-yl)-2-propen-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: (2Z)-1-(2,4-Dichlorophenyl)-3-(dimethylamino)-2-(1H-imidazol-2-yl)-2-propen-1-one(252950-15-5)
• EPA Substance Registry System: (2Z)-1-(2,4-Dichlorophenyl)-3-(dimethylamino)-2-(1H-imidazol-2-yl)-2-propen-1-one(252950-15-5)

Safety Data

• Hazardous Substances Data: 252950-15-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(2Z)-1-(2,4-Dichlorophenyl)-3-(dimethylamino)-2-(1H-imidazol-2-yl)-2-propen-1-one is used as an intermediate in the preparation of glycogen synthase kinase-3 (GSK-3) inhibitors for the development of potential therapeutic agents targeting various diseases and conditions.
Used in Research and Development:
(2Z)-1-(2,4-Dichlorophenyl)-3-(dimethylamino)-2-(1H-imidazol-2-yl)-2-propen-1-one is also utilized in research and development settings to study the effects of GSK-3 inhibition and to develop new compounds with improved potency, selectivity, and pharmacological properties.

Upstream product

• 252950-14-4 1-(2,4-dichlorophenyl)-2-imidazolylethan-1-one 
• 89-75-8 2,4-dichlorobenzoyl chloride 
• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 

Relevant articles and documents

Synthesis, Binding Mode, and Antihyperglycemic Activity of Potent and Selective (5-Imidazol-2-yl-4-phenylpyrimidin-2-yl)[2-(2-pyridylamino)ethyl]amine Inhibitors of Glycogen Synthase Kinase 3

In an effort to identify new antidiabetic agents, we have discovered a novel family of (5-imidazol-2-yl-4-phenylpyrimidin-2-yl)[2-(2-pyridylamino)ethyl]amine analogues which are inhibitors of human glycogen synthase kinase 3 (GSK3). We developed efficient synthetic routes to explore a wide variety of substitution patterns and convergently access a diverse array of analogues. Compound 1 (CHIR-911, CT-99021, or CHIR-73911) emerged from an exploration of heterocycles at the C-5 position, phenyl groups at C-4, and a variety of differently substituted linker and aminopyridine moieties attached at the C-2 position. These compounds exhibited GSK3 IC50s in the low nanomolar range and excellent selectivity. They activate glycogen synthase in insulin receptor-expressing CHO-IR cells and primary rat hepatocytes. Evaluation of lead compounds 1 and 2 (CHIR-611 or CT-98014) in rodent models of type 2 diabetes revealed that single oral doses lowered hyperglycemia within 60 min, enhanced insulin-stimulated glucose transport, and improved glucose disposal without increasing insulin levels.

Inhibitors of glycogen synthase kinase 3

New pyrimidine or pyridine based compounds, compositions and methods of inhibiting the activity of glycogen synthase kinase (GSK3) in vitro and of treatment of GSK3 mediated disorders in vivo are provided. The methods, compounds and compositions of the invention may be employed alone, or in combination with other pharmacologically active agents in the treatment of disorders mediated by GSK3 activity, such as diabetes, Alzheimer's disease and other neurodegenerative disorders, obesity, atherosclerotic cardiovascular disease, essential hypertension, polycystic ovary syndrome, syndrome X, ischemia, traumatic brain injury, bipolar disorder, immunodeficiency or cancer.