139452-21-4

Basic information

• Product Name: 6-Methylpyrazolo[1,5-a]pyridine-3-carboxylic acid
• Synonyms: 6-Methylpyrazolo[1,5-a]pyridine-3-carboxylic acid
• CAS NO: 139452-21-4
• Molecular Formula: C9H8N2O2
• Molecular Weight: 176.17202
• Mol File: 139452-21-4.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 6-Methylpyrazolo[1,5-a]pyridine-3-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Methylpyrazolo[1,5-a]pyridine-3-carboxylic acid(139452-21-4)
• EPA Substance Registry System: 6-Methylpyrazolo[1,5-a]pyridine-3-carboxylic acid(139452-21-4)

Safety Data

• Hazardous Substances Data: 139452-21-4(Hazardous Substances Data)

Upstream product

• 51470-66-7 1-amino-3-methyl-pyridinium 
• 55899-18-8 ethyl 6-methylpyrazolo[1,5-a]pyridine-3-carboxylate 
• 108-99-6 3-Methylpyridine 
• 127717-18-4 methyl 6-methylpyrazolo<1,5-a>pyridine-3-carboxylate 

Downstream Products

• 1356145-20-4 N,2-dimethyl-N'-((6-methylpyrazolo[1,5-a]pyridin-3-yl)methylene)-5-nitrobenzenesulfonohydrazide 

Relevant articles and documents

IMIDAZO [1, 2 -A] PYRIDINE AND PYRAZOLO [1, 5 -A] PYRIDINE DERIVATIVES AS TRPV1 ANTAGONISTS

A compound of formula of formula (I) wherein A represents a single bond, a CH2 group or a CH (Me) group; X1 represents a hydrogen atom, a fluorine atom or a methyl group; X2 represents a hydrogen atom, a fluorine atom, a methyl group or a CH2OH group; X3 represents a hydrogen atom, a fluorine atom or a CH2OH group, and at least two of X1, X2 and X3 are hydrogen; Y represents a C atom and Z represents a N atom or Y represents an N atom and Z represents a C atom. R1 represents a halogen atom, a C1-4 alkyl group, a trifluoromethyl group or a trifluoromethoxy group, and R2 and R3 are each independently selected from a hydrogen atom, a halogen atom, a C1-4 alkyl group, a trifluoromethyl group or a trifluoromethoxy group. or a pharmaceutically acceptable salt or solvate thereof. salt or solvate thereof.

Discovery of pyrazolo[1,5-a]pyridines as p110α-selective PI3 kinase inhibitors

We have made a novel series of pyrazolo[1,5-a]pyridines as PI3 kinase inhibitors, and demonstrated their selectivity for the p110α isoform over the other Class Ia PI3 kinases. We investigated the SAR around the pyrazolo[1,5-a]pyridine ring system, and found compound 5x to be a particularly potent example (p110α IC50 0.9 nM). This compound inhibits cell proliferation and phosphorylation of Akt/PKB, a downstream marker of PI3 kinase activity, and showed in vivo activity in an HCT-116 human xenograft model.

Structure-activity relationship study of EphB3 receptor tyrosine kinase inhibitors

A structure-activity relationship study for a 2-chloroanilide derivative of pyrazolo[1,5-a]pyridine revealed that increased EphB3 kinase inhibitory activity could be accomplished by retaining the 2-chloroanilide and introducing a phenyl or small electron donating substituents to the 5-position of the pyrazolo[1,5-a]pyridine. In addition, replacement of the pyrazolo[1,5-a]pyridine with imidazo[1,2-a]pyridine was well tolerated and resulted in enhanced mouse liver microsome stability. The structure-activity relationship for EphB3 inhibition of both heterocyclic series was similar. Kinase inhibitory activity was also demonstrated for representative analogs in cell culture. An analog (32, LDN-211904) was also profiled for inhibitory activity against a panel of 288 kinases and found to be quite selective for tyrosine kinases. Overall, these studies provide useful molecular probes for examining the in vitro, cellular and potentially in vivo kinase-dependent function of EphB3 receptor.