885518-50-3

Basic information

• Product Name: 4-AMINO-6-BROMO (1H)INDAZOLE
• Synonyms: 4-AMINO-6-BROMOINDAZOLE;4-AMINO-6-BROMO (1H)INDAZOLE;1H-Indazol-4-aMine, 6-broMo-;6-broMo-1H-indazol-4-aMine;Indazol-4-amine, 6-bromo-;6-Bromo-1H-indazol-4-ylamine
• CAS NO: 885518-50-3
• Molecular Formula: C₇H₆BrN₃
• Molecular Weight: 212.05
• Mol File: 885518-50-3.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 426.5±25.0 °C(Predicted)
• Appearance: /
• Density: 1.867±0.06 g/cm3(Predicted)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 14.39±0.40(Predicted)
• CAS DataBase Reference: 4-AMINO-6-BROMO (1H)INDAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-AMINO-6-BROMO (1H)INDAZOLE(885518-50-3)
• EPA Substance Registry System: 4-AMINO-6-BROMO (1H)INDAZOLE(885518-50-3)

Safety Data

• Hazardous Substances Data: 885518-50-3(Hazardous Substances Data)

Usage

Uses

6-Bromo-1H-indazol-4-amine is used as a reagent in the synthesis of indazole derivatives as PI3 kinase inhibitors useful in the treatment of PI3 kinase-mediated diseases.

Upstream product

• 864550-40-3 5-bromo-2-methyl-3-nitroaniline 
• 95192-64-6 5-bromo-2-methyl-1,3-dinitrobenzene 
• 606-20-2 2,6-dinitrotoluene 
• 885518-46-7 6-bromo-4-nitro-1H-indazole 
• 885518-99-0 6-bromo-4-chloro-1H-indazole 

Downstream Products

• 1312012-07-9 C₁₅H₁₃BrN₄O₃S 
• 1312012-06-8 C₁₄H₁₀BrClN₄O₃S 

Relevant articles and documents

X-ray Structure-Guided Discovery of a Potent, Orally Bioavailable, Dual Human Indoleamine/Tryptophan 2,3-Dioxygenase (hIDO/hTDO) Inhibitor That Shows Activity in a Mouse Model of Parkinson’s Disease

Human indoleamine 2,3-dioxygenase 1 (hIDO1) and tryptophan 2,3-dioxygenase (hTDO) have been closely linked to the pathogenesis of Parkinson’s disease (PD); nevertheless, development of dual hIDO1 and hTDO inhibitors to evaluate their potential efficacy against PD is still lacking. Here, we report biochemical, biophysical, and computational analyses revealing that 1H-indazole-4-amines inhibit both hIDO1 and hTDO by a mechanism involving direct coordination with the heme ferrous and ferric states. Crystal structure-guided optimization led to23, which manifested IC50values of 0.64 and 0.04 μM to hIDO1 and hTDO, respectively, and had good pharmacokinetic properties and brain penetration in mice.23showed efficacy against the 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine-induced mouse motor coordination deficits, comparable to Madopar, an anti-PD medicine. Further studies revealed that different from Madopar,23likely has specific anti-PD mechanisms involving lowering IDO1 expression, alleviating dopaminergic neurodegeneration, reducing inflammatory cytokines and quinolinic acid in mouse brain, and increasing kynurenic acid in mouse blood.

Indazole compounds containing nitrogen substituents, and application of same as IDO inhibitors

The invention discloses nitrogen substituent-containing indazole compounds as shown in a formula (I) which is described in the specification, a preparation method for the compounds, and application ofthe compounds as IDO inhibitors. The compounds provided by the invention can be used for preventing and/or treating a plurality of diseases, such as Alzheimer's disease, cataract, infections relatedto cellular immune activation, autoimmune diseases, AIDS, cancers, depression, the metabolic disorder of tryptophan or the like.

Method for preparing 1H-indazole derivative

The invention discloses a method for preparing a 1H-indazole derivative. The method takes a compound as a formula (A1) or a compound as a formula (A2) as raw materials, and the compound as the formula(A1) and the compound as the formula (A2) are subjected