51065-76-0

Basic information

• Product Name: 2-PHENYL-PYRAZOLO[1,5-A]PYRIDINE-3-CARBOXYLIC ACID ETHYL ESTER
• Synonyms: 2-PHENYL-PYRAZOLO[1,5-A]PYRIDINE-3-CARBOXYLIC ACID ETHYL ESTER
• CAS NO: 51065-76-0
• Molecular Formula: C₁₆H₁₄N₂O₂
• Molecular Weight: 266.29
• Mol File: 51065-76-0.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-PHENYL-PYRAZOLO[1,5-A]PYRIDINE-3-CARBOXYLIC ACID ETHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 2-PHENYL-PYRAZOLO[1,5-A]PYRIDINE-3-CARBOXYLIC ACID ETHYL ESTER(51065-76-0)
• EPA Substance Registry System: 2-PHENYL-PYRAZOLO[1,5-A]PYRIDINE-3-CARBOXYLIC ACID ETHYL ESTER(51065-76-0)

Safety Data

• Hazardous Substances Data: 51065-76-0(Hazardous Substances Data)

Usage

Uses

Used in Medicinal Chemistry:
2-PHENYL-PYRAZOLO[1,5-A]PYRIDINE-3-CARBOXYLIC ACID ETHYL ESTER is used as a compound with potential pharmacological activity for targeting biological systems. Its unique structure allows it to engage with specific biological targets, making it a candidate for further research and development in the field of medicine.
Used as a Precursor in Organic Synthesis:
In the chemical industry, 2-PHENYL-PYRAZOLO[1,5-A]PYRIDINE-3-CARBOXYLIC ACID ETHYL ESTER serves as a precursor in the synthesis of other organic compounds. Its versatile structure can be modified or used as a building block to create a variety of molecules with different properties and applications.
Used in Biological and Pharmacological Research:
2-PHENYL-PYRAZOLO[1,5-A]PYRIDINE-3-CARBOXYLIC ACID ETHYL ESTER is utilized in research settings to study its biological and pharmacological properties. Understanding its interactions with biological systems can lead to the discovery of new therapeutic agents or insights into disease mechanisms.

Upstream product

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• 100-47-0 benzonitrile 
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Downstream Products

• 1414572-88-5 2-phenylpyrazolo[1,5-a]pyridine-3-carboxylic acid hydrochloride 
• 56983-95-0 2-phenylpyrazolo[1,5-a]pyridine 
• 121524-18-3 (2R)-1-[3-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)acryloyl]-2-(2-hydroxyethyl)piperidine 
• 71727-37-2 2-phenyl-pyrazolo[1,5-a]pyridine-3-carbaldehyde 
• 127717-25-3 3-(hydroxymethyl)-2-phenylpyrazolo<1,5-a>pyridine 
• 80537-07-1 2-phenylpyrazolo[1,5-a]pyridine-3-carboxylic acid 
• 80537-00-4 2-Phenyl-pyrazolo[1,5-a]pyridine-3-carboxylic acid (3-hydroxy-propyl)-amide 
• 80537-01-5 2-Phenyl-pyrazolo[1,5-a]pyridine-3-carboxylic acid (2-hydroxy-butyl)-amide 

Relevant articles and documents

Preparation method of pyrazolo[1,5-a]pyridine derivative

The invention discloses a preparation method of pyrazolo[1,5-a]pyridine derivatives, and belongs to the field of organic synthesis. The problems that an existing pyrazolo[1,5-a]pyridine structure synthesis method needs metal catalysis, the substrate range is limited, the total yield of multi-step reaction is low, stoichiometric additives, toxic oxidants and oxygen-free technologies are adopted, and reaction conditions are harsh are solved. The method comprises the steps: dissolving pyridinium salt, unsaturated alkene and 2,3-dichloro-5,6-dicyanobenzoquinone in an organic solvent, dropwise adding triethylamine to react, concentrating by a rotary evaporator to remove the solvent, and separating and purifying by silica gel column chromatography to obtain the pyrazolo[1,5-a]pyridine derivative.

Synthesis of Functionalized Pyrazolo[1,5-a]pyridines: [3+2] Cycloaddition of N-Aminopyridines and α,β-Unsaturated Carbonyl Compounds/Alkenes at Room Temperature

The synthesis of functionalized pyrazolo[1,5-a]pyridines through oxidative [3+2] cycloaddition of N-aminopyridines with α,β-unsaturated carbonyl compounds or electron-withdrawing olefins is described. The reactions proceed in N-methylpyrrolidone as the solvent under metal-free conditions at room temperature.

Copper-mediated synthesis of pyrazolo[1,5-a]pyridines through oxidative linkage of C-C/N-N bonds

Copper-mediated synthesis of pyrazolo[1,5-a]pyridine-3-carboxylates through oxidative linkage of C-C and N-N bonds under mild reaction conditions is described. This protocol is applicable to a variety of pyridyl esters as well as various benzonitriles including nicotinonitrile, isonicotinonitrile and thiophene-2-carbonitrile. Better yields were observed with electron withdrawing substituted benzonitriles.

BICYCLIC HETEROARYL UREA, THIOUREA, GUANIDINE AND CYANOGUANIDINE COMPOUNDS AS TRKA KINASE INHIBITORS

Compounds of Formula I or stereoisomers, tautomers, or pharmaceutically acceptable salts, solvates or prodrugs thereof, wherein Ring A, Ring C and X are as defined herein, are inhibitors of TrkA kinase and are useful in the treatment of diseases which can be treated with a TrkA kinase inhibitor such as pain, cancer, inflammation/inflammatory diseases, neurodegenerative diseases, certain infectious diseases, Sjogren's syndrome, endometriosis, diabetic peripheral neuropathy, prostatitis and pelvic pain syndrome.

Optimization of the in vitro cardiac safety of hydroxamate-based histone deacetylase inhibitors

Histone deacetylase (HDAC) inhibitors have shown promise in treating various forms of cancer. However, many HDAC inhibitors from diverse structural classes have been associated with QT prolongation in humans. Inhibition of the human ether a-go-go related gene (hERG) channel has been associated with QT prolongation and fatal arrhythmias. To determine if the observed cardiac effects of HDAC inhibitors in humans is due to hERG blockade, a highly potent HDAC inhibitor devoid of hERG activity was required. Starting with dacinostat (LAQ824), a highly potent HDAC inhibitor, we explored the SAR to determine the pharmacophores required for HDAC and hERG inhibition. We disclose here the results of these efforts where a high degree of pharmacophore homology between these two targets was discovered. This similarity prevented traditional strategies for mitigating hERG binding/modulation from being successful and novel approaches for reducing hERG inhibition were required. Using a hERG homology model, two compounds, 11r and 25i, were discovered to be highly efficacious with weak affinity for the hERG and other ion channels.

Process development of a novel non-xanthine adenosine A1 receptor antagonist

(+)-(R)-1-[(E)-3-(2-phenylpyrazolo[l,5-a]pyridin-3-yl)acryloyl]-2- piperidine ethanol (FK453) is a novel, potent adenosine AI receptor antagonist for the regulation of renal function. The development of a reliable process suitable for large scale manufacture is described. A Horner-Emmons reaction and a 1,3-dipolar cycloaddition were successfully scaled up to afford ethyl (E)-3-(2-phenylpyrazolo[l,5-a]pyridin-3-yl)acryloylate, with excellent regioselectivity and stereoselectivity. Process improvements and optimization of each step permitted elimination of column chromatography, resulting in a straightforward, practical synthesis of FK453.

Preparation of New Nitrogen-Bridged Heterocycles. XIV. Further Investigation of the Desulfurization and the Rearrangement of Pyrido-1,3,4-thiadiazine Intermediates

The formation of pyrazolopyridine derivatives via the desulfurization and the rearrangement of pyrido-1,3,4-thiadiazine intermediates having various substituents at the 2- and 4-positions was investigated, and the wide applicability of this

1,3-Dipolar Addition of Pyridine N-Imine to Acetylenes and the Use of C-13 NMR in Several Structural Assignments

Addition of pyridine-N-imine to a variety of acetylenic mono- (Scheme I) and di- (Scheme II) carboxylic ester dipolarophiles was carried out.Several of the 3-azapyrrocoline esters obtained were further converted into acids, amides and hydrazides as shown in Schemes I and II.