76006-08-1

Basic information

• Product Name: 5-CHLORO-1H-PYRAZOLO[3,4-C]PYRIDINE
• Synonyms: 5-CHLORO-1H-PYRAZOLO[3,4-C]PYRIDINE;1H-Pyrazolo[3,4-c]pyridine,5-chloro-;5-chloro-1H-pyrazolo[3;5-Chloro-1H-pyrazolo[3,4-...
• CAS NO: 76006-08-1
• Molecular Formula: C₆H₄ClN₃
• Molecular Weight: 153.57
• Product Categories: Heterocycle-Pyridine series
• Mol File: 76006-08-1.mol
• Article Data: 5

Chemical Properties

• Melting Point: 184-185 °C
• Boiling Point: 357.5°C at 760 mmHg
• Flash Point: 201.2°C
• Appearance: /
• Density: 1.531g/cm³
• Vapor Pressure: 5.6E-05mmHg at 25°C
• Refractive Index: 1.72
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 9.74±0.40(Predicted)
• CAS DataBase Reference: 5-CHLORO-1H-PYRAZOLO[3,4-C]PYRIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-CHLORO-1H-PYRAZOLO[3,4-C]PYRIDINE(76006-08-1)
• EPA Substance Registry System: 5-CHLORO-1H-PYRAZOLO[3,4-C]PYRIDINE(76006-08-1)

Safety Data

• Hazardous Substances Data: 76006-08-1(Hazardous Substances Data)

Usage

General Description

5-CHLORO-1H-PYRAZOLO[3,4-C]PYRIDINE is a chemical compound that belongs to the pyrazolo[3,4-c]pyridine family. It is commonly used in the pharmaceutical industry as a building block for the synthesis of various bioactive compounds and drugs. 5-CHLORO-1H-PYRAZOLO[3,4-C]PYRIDINE is characterized by the presence of a chlorine atom on the 5th position of the pyrazole ring, which gives it unique chemical and biological properties. It has been studied for its potential as an anti-inflammatory and anti-cancer agent, and its structure also makes it a promising candidate for the development of new drug molecules. Additionally, 5-CHLORO-1H-PYRAZOLO[3,4-C]PYRIDINE is used in chemical research and synthesis, and its versatile nature makes it a valuable tool for the design and production of novel compounds with therapeutic applications.

InChI:InChI=1/C6H4ClN3/c7-6-1-4-2-9-10-5(4)3-8-6/h1-3H,(H,9,10)

Upstream product

• 6635-92-3 5-acetamido-2-chloro-4-methylpyridine 
• 23056-33-9 2-chloro-4-methyl-5-nitro-pyridine 

Relevant articles and documents

Synthesis, docking study and kinase inhibitory activity of a number of new substituted pyrazolo[3,4-c]pyridines

A series of new pyrazolo[3,4-c]pyridines bearing various 1, 3, 5 or 1, 3, 7 pattern substitutions, were designed and synthesized. Some of them showed interesting inhibitory activity mainly against glycogen synthase kinase 3 (GSK3)α/β as well as against cdc2-like kinases 1 (CLK1) and dual-specificity tyrosine phosphorylation-regulated kinase 1A (DYRK1A), with good selectivity and remarkable structure-activity relationships (SARs), without being cytotoxic. Molecular simulations in correlation with biological data revealed the importance of the existence of N1-H as well as the absence of a bulky 7-substituent.

Novel pyrazolopyridine derivatives as potential angiogenesis inhibitors: Synthesis, biological evaluation and transcriptome-based mechanistic analysis

Modified purine derivatives exemplified by pyrazolopyrimidines have emerged as highly selective inhibitors of several angiogenic receptor tyrosine kinases. Herein, we designed and synthesized a new series of substituted pyrazolopyridines and explored their ability to influence crucial pro-angiogenic attributes of endothelial cells. Four of the synthesized compounds, possessing analogous substitution pattern, were found able to inhibit at low micromolar concentrations endothelial cell proliferation, migration and differentiation, constitutively or in response to Vascular Endothelial Growth Factor (VEGF) and to attenuate VEGF-induced phosphorylation of VEGF receptor-2 and downstream kinases AKT and ERK1/2. Administration of effective compounds in mice delayed the growth of syngeneic Lewis lung carcinoma transplants and reduced tumor microvessel density, without causing toxicity. Genome-wide microarray and gene ontology analyses of treated endothelial cells revealed derivative 18c as the most efficient modulator of gene expression and mitotic cell cycle/cell divisiong along with ? cholesterol biosynthesis? as the most significantly altered biological processes.

Pyrazolopyridines. Part 5. Preparation and Reactions of Pyrazolopyridines

A series of pyrazolopyridines has been prepared by nitrosation of 3-acetamido-4-methylpyridines and subsequent rearrangement and cyclisation of the N-acetyl-N-nitroso-compounds produced.The reactions of the pyrazolopyridines have been investigated. 1- and 2-Acetyl and 1- and 2-benzyl compounds were obtained and their structures elucidated spectroscopically.The ring system readily undergoes electrophilic substitution in the 3-position. 7-Chloropyrazolopyridine has been shown to be more susceptible to nucleophilic substitution than the isomeric 5-chloro-compound.