916325-85-4

Basic information

• Product Name: 5-BROMO-1H-PYRAZOLO[3,4-B]PYRIDINE-3-CARBOXYLIC ACID
• Synonyms: 5-BROMO-1H-PYRAZOLO[3,4-B]PYRIDINE-3-CARBOXYLIC ACID;1H-Pyrazolo[3,4-b]pyridine-3-carboxylic acid, 5-broMo-
• CAS NO: 916325-85-4
• Molecular Formula: C₇H₄BrN₃O₂
• Molecular Weight: 242.04
• Mol File: 916325-85-4.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 492.256 °C at 760 mmHg
• Flash Point: 251.507 °C
• Appearance: /
• Density: 2.068g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.785
• Storage Temp.: 2-8°C
• PKA: 1.89±0.30(Predicted)
• CAS DataBase Reference: 5-BROMO-1H-PYRAZOLO[3,4-B]PYRIDINE-3-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 5-BROMO-1H-PYRAZOLO[3,4-B]PYRIDINE-3-CARBOXYLIC ACID(916325-85-4)
• EPA Substance Registry System: 5-BROMO-1H-PYRAZOLO[3,4-B]PYRIDINE-3-CARBOXYLIC ACID(916325-85-4)

Safety Data

• RIDADR: UN2811
• Hazardous Substances Data: 916325-85-4(Hazardous Substances Data)

Usage

General Description

5-Bromo-1H-pyrazolo[3,4-b]pyridine-3-carboxylic acid is a chemical compound with the molecular formula C8H5BrN4O2. It is a pyrazolopyridine derivative and has a bromine atom attached to the pyrazole ring. 5-Bromo-1H-pyrazolo[3,4-b]pyridine-3-carboxylic acid has potential biological and pharmacological activities and is often used as a building block in the synthesis of pharmaceuticals and agrochemicals. It may also have use in the development of new materials and organic electronic devices due to its unique chemical structure. Additionally, 5-Bromo-1H-pyrazolo[3,4-b]pyridine-3-carboxylic acid is of interest to researchers in the fields of medicinal chemistry and organic synthesis for its diverse reactivity and potential for creating new molecules with desired properties.

InChI:InChI=1/C7H4BrN3O2/c8-3-1-4-5(7(12)13)10-11-6(4)9-2-3/h1-2H,(H,12,13)(H,9,10,11)

Upstream product

• 875781-18-3 5-bromo-3-iodo-1H-pyrazolo[3,4-b]pyridine 
• 201230-82-2 carbon monoxide 
• 875781-17-2 5-bromo-7-azaindazole 
• 116855-08-4 1H-pyrazolo[3,4-b]pyridine-3-carboxylic acid 
• 131674-39-0 2-chloro-3-(1-hydroxyethyl)pyridine 
• 109-09-1 2-chloropyridine 
• 55676-21-6 3-acetyl-2-chloropyridine 
• 116834-96-9 3-methyl-1H-pyrazolo[3,4b]pyridine 
• 885223-65-4 5-bromo-3-methyl-1H-pyrazolo[3,4-b]pyridine 
• 916325-83-2 pyrazolo[3,4-b]pyridine-3-carboxylic acid methyl ester 
• 916325-84-3 methyl 5-bromo-1H-pyrazolo[3,4-b]pyridine-3-carboxylate 

Downstream Products

• 948834-63-7 C₁₅H₁₄O₂N₅Br 
• 948834-64-8 C₁₈H₂₀N₇OBr 
• 948834-65-9 C₁₇H₁₇N₆O₂Br 
• 948834-70-6 C₂₀H₂₆N₅O₂BrSi 
• 1346169-41-2 N-(2-aminophenyl)-5-bromo-1H-pyrazolo[3,4-b]pyridin-3-carboxamide 
• 1314734-59-2 1-(tetrahydro-2H-pyran-2-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazolo[3,4-b]pyridine-3-carbaldehyde 
• 1246614-23-2 N-(3-(5-bromo-1H-pyrazolo[3,4-b]pyridine-3-carbonyl)-2,4-difluorophenyl)propane-1-sulfonamide 

Relevant articles and documents

Design and synthesis of 1H-pyrazolo[3,4-b]pyridines targeting mitogen-activated protein kinase kinase 4 (MKK4) - A promising target for liver regeneration

Currently, the therapeutic options for treatment of liver failure are very limited. As mitogen-activated protein kinase kinase 4 (MKK4) has recently been identified by in vivo RNAi experiments to be a major regulator in hepatocyte regeneration, we pursued the development of a small molecule targeting this protein kinase. Starting from the approved BRAFV600E inhibitor vemurafenib (8), that showed a high off-target affinity to MKK4 in an initial screening, we followed a scaffold-hopping approach, changing the core heterocycle from 1H-pyrrolo[2,3-b]pyridine to 1H-pyrazolo[2,3-b]pyridine (10). Affinity to MKK4 could be conserved while the selectivity against off-target protein kinases was slightly improved. Further modifications led to 58 and 59 showing high affinity to MKK4 in the low nanomolar range and excellent selectivity profile from mandatory multiparameter-optimization for the essential anti-targets (MKK7, JNK1) and off-targets (BRAF, MAP4K5, ZAK) in the MKK4 pathway. Herein we report the first selective MKK4 inhibitors in this class.

PROTEIN KINASE MKK4 INHIBITORS FOR PROMOTING LIVER REGENERATION OR REDUCING OR PREVENTING HEPATOCYTE DEATH

The invention relates to pyrazolo-pyridine compounds which inhibit mitogen-activated protein kinase kinase 4 (MKK4) and in particular, selectively inhibit MKK4 over protein kinases JNK1 and MKK7. The compounds are useful for promoting liver regeneration or reducing or preventing hepatocyte death. They are further useful for treating osteoarthritis or rheumatoid arthritis, or CNS-related diseases.

3-(3H-IMIDAZO[4,5-B]PYRIDIN-2-YL)-1H-PYRAZOLO[3,4-B]PYRIDINE AND THERAPEUTIC USES THEREOF

Azaindazole compounds for treating various diseases and pathologies are disclosed. More particularly, the present invention concerns the use of an azaindazole compound or analogs thereof, in the treatment of disorders characterized by the activation of Wnt pathway signaling (e.g., cancer, abnormal cellular proliferation, angiogenesis, fibrotic disorders, bone or cartilage diseases, and osteoarthritis), the modulation of cellular events mediated by Wnt pathway signaling, as well as genetic diseases and neurological conditions/disorders/diseases due to mutations or dysregulation of the Wnt pathway and/or of one or more of Wnt signaling components. Also provided are methods for treating Wnt-related disease states.