885518-46-7

Basic information

• Product Name: 6-BROMO-4-NITRO-1H-INDAZOLE
• Synonyms: 6-BROMO-4-NITRO-1H-INDAZOLE;1H-Indazole,6-broMo-4-nitro-;6-Bromo-4-nitro-1H-indazole 95%;6-Bromo-4-nitro-1H-indazole95%
• CAS NO: 885518-46-7
• Molecular Formula: C₇H₄BrN₃O₂
• Molecular Weight: 242.03
• Product Categories: Building Blocks;Indazole;Indazoles
• Mol File: 885518-46-7.mol

Chemical Properties

• Boiling Point: 420.8±25.0 °C(Predicted)
• Appearance: /
• Density: 1.965
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 9.86±0.40(Predicted)
• CAS DataBase Reference: 6-BROMO-4-NITRO-1H-INDAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-BROMO-4-NITRO-1H-INDAZOLE(885518-46-7)
• EPA Substance Registry System: 6-BROMO-4-NITRO-1H-INDAZOLE(885518-46-7)

Safety Data

• Hazard Codes: T
• Statements: 25
• Safety Statements: 45
• RIDADR: 2811
• HazardClass: IRRITANT
• PackingGroup: Ⅲ
• Hazardous Substances Data: 885518-46-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
6-Bromo-4-nitro-1H-indazole is used as a reagent for the preparation of 1,2,4-triazine-6-carboxamide derivatives with an acetamide group. These derivatives act as Syk kinase inhibitors, which have potential applications in the treatment of cancer, allergy, or autoimmune diseases. By inhibiting Syk kinase, these compounds can modulate immune responses and potentially provide therapeutic benefits for patients suffering from these conditions.

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 

Downstream Products

• 1198437-02-3 6-bromo-3-fluoro-4-nitro-1H-indazole 
• 1198437-98-7 6-bromo-3-fluoro-4-nitro-1-(phenylsulfonyl)-1H-indazole 
• 1198438-00-4 6-bromo-3-fluoro-1-(phenylsulfonyl)-1H-indazol-4-amine 
• 1198438-02-6 3-fluoro-1-(phenylsulfonyl)-6-(trimethylstannanyl)-1H-indazol-4-amine 
• 1198438-06-0 3-fluoro-6-{6-fluoro-1-[(4-nitrophenyl)sulfonyl]-1H-indol-4-yl}-1-(phenylsulfonyl)-1H-indazol-4-amine 
• 1310556-75-2 3-fluoro-6-(1H-indol-4-yl)-1-(phenylsulfonyl)-1H-indazol-4-amine 
• 1310556-83-2 3-fluoro-6-[2-methyl-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-1-(phenylsulfonyl)-1H-indazol-4-amine 
• 1309785-54-3 3-fluoro-6-{1-[(4-methylphenyl)sulfonyl]-1H-pyrazolo[3,4-b]pyridin-5-yl}-1-(phenylsulfonyl)-1H-indazol-4-amine 
• 1309778-73-1 N-{6-[5-({[4-chloro-3-(trifluoromethyl)phenyl]sulfonyl}amino)-6-(methyloxy)-3-pyridinyl]-1H-indazol-4-yl}-2-methyl-1,3-thiazole-4-carboxamide 
• 1309778-57-1 {[3-(4-{[(2-methyl-1,3-thiazol-4-yl)carbonyl]amino}-1H-indazol-6-yl)phenyl]oxy}acetic acid 
• 1198408-81-9 N-(6-(1H-indol-4-yl)-1H-indazol-4-yl)benzamide 
• 1309778-60-6 N-(6-{6-chloro-5-[methyl(phenylsulfonyl)amino]-3-pyridinyl}-1H-indazol-4-yl)-2-methyl-1,3-thiazole-4-carboxamide 
• 1309778-62-8 N-(6-{6-chloro-5-[(phenylsulfonyl)methyl]-3-pyridinyl}-1H-indazol-4-yl)-2-methyl-1,3-thiazole-4-carboxamide 
• 1198804-08-8 N-(6-{4-chloro-3-[(methylsulfonyl)amino]phenyl}-1H-indazol-4-yl)-2-methyl-1,3-thiazole-4-carboxamide 

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.

4,6-Substituted-1H-Indazoles as potent IDO1/TDO dual inhibitors

Indoleamine 2,3-dioxygenase 1 (IDO1) and tryptophan 2,3-dioxygenase (TDO) are constitutively overexpressed in many types of cancer cells and exert important immunosuppressive functions. In this article, a series of 4,6-substituted-1H-indazole derivatives were synthesized and evaluated the inhibitory activities against IDO1 and TDO, as well as their structure-activity relationships (SARs). Among these, compound 35 displayed the most IDO1 inhibitory potency with an IC50 value of 0.74 μM in an enzymatic assay and 1.37 μM in HeLa cells. Quantitative analysis of the Western blot results indicated that 35 significantly decreased the INFγ-induced IDO1 expression in a concentration-dependent manner. In addition, 35 showed promising TDO inhibition with an IC50 value of 2.93 μM in the enzymatic assay and 7.54 μM in A172 cells. Moreover, compound 35 exhibited in vivo antitumor activity in the CT26 xenograft model. These findings suggest that 1H-indazole derivative 35 is a potent IDO1/TDO dual inhibitor, and has the potential to be developed for IDO1/TDO-related cancer treatment.

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

Indazole compounds and application thereof to preparation of IDO inhibitors

The invention discloses indazole compounds as shown in a formula (i) or (II) which is described in the specification, and a preparation method thereof, and application of the 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 related to cellular immune activation,autoimmune diseases, AIDS, cancers, depression, the metabolic disorder of tryptophan or the like.

Polysubstituted-indazole compounds and application of same as IDO inhibitors

The invention discloses polysubstituted-indazole compounds as shown in a formula (I) which is described in the specification, a preparation method for the compounds, and application of the 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 related to cellular immune activation, autoimmune diseases, AIDS, cancers, depression, the metabolic disorder of tryptophan or the like.