676371-00-9

Basic information

• Product Name: 6-BROMO-IMIDAZO[1,2-A]PYRIDIN-8-AMINE
• Synonyms: 6-bromo-1H-imidazo [1,2-a]pyridine-8-amine;8-Amino-6-bromoimidazo[1,2-a]pyridine;6-Bromo-1H-imidazo[1,2-a]pyridin-8-amine;2-a] pyridin-8-aMine;6-broMoiMidazo[1;6-bromo-1,5-dihydroimidazo[1,2-a]pyridine-8-carboxylic acid;6-BROMO-IMIDAZO[1,2-A]PYRIDIN-8-AMINE;6-bromoH-imidazo[1,2-a]pyridine-8-carboxylic acid
• CAS NO: 676371-00-9
• Molecular Formula: C₇H₆BrN₃
• Molecular Weight: 212.05
• Product Categories: CHIRAL CHEMICALS
• Mol File: 676371-00-9.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• Density: 1.878 g/cm³
• Refractive Index: 1.728
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 6.31±0.50(Predicted)
• CAS DataBase Reference: 6-BROMO-IMIDAZO[1,2-A]PYRIDIN-8-AMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-BROMO-IMIDAZO[1,2-A]PYRIDIN-8-AMINE(676371-00-9)
• EPA Substance Registry System: 6-BROMO-IMIDAZO[1,2-A]PYRIDIN-8-AMINE(676371-00-9)

Safety Data

• Hazard Codes: Xn
• Statements: 22-43
• Safety Statements: 36/37
• Hazardous Substances Data: 676371-00-9(Hazardous Substances Data)

Usage

General Description

6-Bromo-imidazo[1,2-a]pyridin-8-amine is a chemical compound with the molecular formula C7H6BrN3. It is a heterocyclic compound containing both imidazole and pyridine rings. This chemical has a bromine atom attached to the imidazole ring and an amine group attached to the pyridine ring. It is commonly used in the pharmaceutical and chemical industries for the synthesis of various drugs and biologically active compounds. Additionally, it is a versatile building block in organic synthesis and medicinal chemistry due to its reactivity and biological activity.

InChI:InChI=1/C8H5BrN2O2/c9-5-3-6(8(12)13)7-10-1-2-11(7)4-5/h1-4H,(H,12,13)

Upstream product

• 38875-53-5 5-bromo-pyridine-2,3-diamine 
• 2032-35-1 Bromoacetaldehyde diethyl acetal 
• 107-20-0 2-chloroethanal 
• 17157-48-1 bromoacetaldehyde 

Downstream Products

• 1161846-73-6 N-[3-(8-aminoimidazo[1,2-a]pyridin-6-yl)-2-methylphenyl]-4-tert-butylbenzamide 
• 1161847-43-3 pyrrolidine-1-carboxylic acid [3-(8-aminoimidazo[1,2-a]pyridin-6-yl)-2-methylphenyl]amide 
• 1160994-94-4 8-aminoimidazo[1,2-a]pyridine-6-carboxylic acid methyl ester 
• 1161846-71-4 4-tert-butyl-N-{2-methyl-3-[8-({5-[(morpholin-4-yl)carbonyl]pyridin-2-yl}amino)imidazo[1,2-a]pyridin-6-yl]phenyl}benzamide 
• 1402595-20-3 tert-butyl {6-bromo-3-[4-(cyclopropylcarbamoyl)-3-methylphenyl]imidazo[1,2-a]pyridin-8-yl}(3,3,3-trifluoropropyl)carbamate 
• 1402593-38-7 N-cyclopropyl-4-{6-(2-fluoro-4-methoxyphenoxy)-8-[(3,3,3-trifluoropropyl)amino]imidazo[1,2-a]pyridin-3-yl}-2-methylbenzamide 
• 1402593-37-6 N-cyclopropyl-4-{6-(3-fluorophenoxy)-8-[(3,3,3-trifluoropropyl)amino]imidazo[1,2-a]pyridin-3-yl}-2-methylbenzamide 
• 1402593-36-5 C₂₂H₂₃F₃N₄O₃S 
• 1402593-35-4 N-cyclopropyl-2-methyl-4-{6-(methylsulfanyl)-8-[(3,3,3-trifluoropropyl)amino]imidazo[1,2-a]pyridin-3-yl}benzamide 
• 1402593-29-6 N-cyclopropyl-4-{6-[(3-fluoro-5-methylphenyl)sulfanyl]-8-[(3,3,3-trifluoropropyl)amino]imidazo[1,2-a]pyridin-3-yl}-2-methylbenzamide 
• 1402593-27-4 N-cyclopropyl-4-{6-[2-(hydroxymethyl)phenyl]-8-[(3,3,3-trifluoropropyl)amino]imidazo[1,2-a]pyridin-3-yl}-2-methylbenzamide 
• 1402596-16-0 tert-butyl {6-bromo-3-[4-(cyclopropylcarbamoyl)-3-methylphenyl]imidazo[1,2-a]pyridin-8-yl}(2,2-difluoroethyl)carbamate 
• 1402596-15-9 tert-butyl {3-[4-(cyclopropylcarbamoyl)-3-methylphenyl]-6-(3-fluorophenoxy)imidazo[1,2-a]pyridin-8-yl}(2,2-difluoroethyl)carbamate 
• 1402594-95-9 N-cyclopropyl-4-{8-[(2,2-difluoroethyl)amino]-6-(3-fluorophenoxy)imidazo[1,2-a]pyridin-3-yl}-2-methylbenzamide 

Relevant articles and documents

From Synthetic Simplified Marine Metabolite Analogues to New Selective Allosteric Inhibitor of Aurora B Kinase

Significant inhibition of Aurora B was achieved by the synthesis of simplified fragments of benzosceptrins and oroidin belonging to the marine pyrrole-2-aminoimidazoles metabolites isolated from sponges. Evaluation of kinase inhibition enabled the discovery of a synthetically accessible rigid acetylenic structural analogue EL-228 (1), whose structure could be optimized into the potent CJ2-150 (37). Here we present the synthesis of new inhibitors of Aurora B kinase, which is an important target for cancer therapy through mitosis regulation. The biologically oriented synthesis yielded several nanomolar inhibitors. The optimized compound CJ2-150 (37) showed a non-ATP competitive allosteric mode of action in a mixed-type inhibition for Aurora B kinase. Molecular docking identified a probable binding mode in the allosteric site "F"and highlighted the key interactions with the protein. We describe the improvement of the inhibitory potency and specificity of the novel scaffold as well as the characterization of the mechanism of action.

Structure-based drug design of RN486, a potent and selective Bruton's tyrosine kinase (BTK) inhibitor, for the treatment of rheumatoid arthritis

Structure-based drug design was used to guide the optimization of a series of selective BTK inhibitors as potential treatments for Rheumatoid arthritis. Highlights include the introduction of a benzyl alcohol group and a fluorine substitution, each of which resulted in over 10-fold increase in activity. Concurrent optimization of drug-like properties led to compound 1 (RN486) (J. Pharmacol. Exp. Ther. 2012, 341, 90), which was selected for advanced preclinical characterization based on its favorable properties.

NOVEL IMIDAZO[1,2-A]PYRIDINE AND IMIDAZO[1,2-B]PYRIDAZINE DERIVATIVES

Imidazo[1,2-a]pyridine and imidazo[1,2-b]pyridazine derivatives which inhibit Btk and are useful for the treatment of auto-immune and inflammatory diseases caused by aberrant B-cell activation, e.g. arthritis.