6635-92-3

Usage

Chemical Properties

White solid

InChI:InChI=1/C8H9ClN2O/c1-5-3-8(9)10-4-7(5)11-6(2)12/h3-4H,1-2H3,(H,11,12)

Upstream product

• 108-24-7 acetic anhydride 
• 66909-38-4 5-amino-2-chloro-4-methylpyridine 
• 23056-33-9 2-chloro-4-methyl-5-nitro-pyridine 
• 21901-41-7 2-hydroxy-4-methyl-5-nitropyridine 
• 21901-40-6 2-amino-5-nitro-4-picoline 

Downstream Products

• 76006-08-1 5-chloro-1H-pyrazolo<3,4-c>pyridine 
• 76006-04-7 1-acetyl-5-chloro-1H-pyrazolo<3,4-c>pyridine 
• 76006-08-1 5-chloropyrazolo[3,4-c]pyridine 
• 1951402-78-0 5,7-dichloro-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-c]pyridine 

Relevant academic research and scientific papers

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.

The discovery of new cytotoxic pyrazolopyridine derivatives

A number of new 3,7-disubstituted pyrazolo[3,4-c]pyridines have been designed and synthesized from suitable 2-aminopyridines. The antiproliferative activity of the derivatives was determined against the pancreatic MIA PaCa-2 and ovarian SCOV3 cancer cell-lines. IC50values of the most promising analogue 46 lie in the submicromolar or low micromolar range. Furthermore, compound 46 shows similar inhibitory activities against DU145, A2058 and PC-3 cancer cells, blocks the cell cycle at the G0/G1phase and induce apoptosis, as determined by the appearance of apoptotic nuclei.

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.