20208-81-5

Usage

Structure

Pyridine ring fused to a pyrazole ring The compound has a bicyclic structure with a pyridine ring (a six-membered nitrogen-containing ring) fused to a pyrazole ring (a five-membered nitrogen-containing ring).

Phenyl group attachment

To the nitrogen atom A phenyl group (a carbon ring with delocalized electrons) is attached to one of the nitrogen atoms in the pyrazole ring.

Heterocyclic compound

Containing a ring structure with both carbon and nitrogen atoms The compound's structure includes multiple nitrogen atoms within the ring systems, making it a heterocyclic compound.

Potential use as a drug molecule

Ability to bind to certain receptors in the central nervous system 1-phenyl-1H-pyrazolo[3,4-b]pyridine has been studied for its potential as a drug due to its ability to interact with specific receptors in the brain.

Biological activities of derivatives

Anti-inflammatory and anti-cancer properties Researchers have investigated the biological activities of various derivatives of 1-phenyl-1H-pyrazolo[3,4-b]pyridine, finding that some exhibit anti-inflammatory and anti-cancer effects.

Promise for pharmaceutical development

Further study in the development of new pharmaceutical agents The compound and its derivatives have shown potential for further research, with the aim of developing new drugs for various medical conditions.

Upstream product

• 100-63-0 phenylhydrazine 
• 128071-75-0 2-bromopyridine-3-carboxaldehyde 
• 591-50-4 iodobenzene 
• 271-73-8 1H-Pyrazolo[3,4-b]pyridine 
• 59-88-1 phenylhydrazine hydrochloride 
• 36404-88-3 2-chloro-3-carbaldehydepyridine 
• 1246849-53-5 (E)-2-(phenylamino)nicotinaldehyde oxime 
• 5334-43-0 5-Amino-4-cyano-1-phenylpyrazole 
• 826-85-7 1-phenylpyrazol-5-amine 
• 102-52-3 malonaldehydebis(dimethylacetal) 

Downstream Products

• 116855-17-5 1-Phenyl-1H-pyrazolo[3,4-b]pyridine-6-carboxylic acid amide 

Relevant academic research and scientific papers

Copper-catalyzedortho-selective direct sulfenylation ofN-aryl-7-azaindoles with disulfides

A copper-catalyzed direct C-H chalcogenation ofN-aryl-azaindoles with disulfides is described. This transformation was performed using Earth abundant Cu(OAc)2as a catalyst, benzoic acid as an additive, air as a terminal oxidant, and readily available diaryl and dialkyldisulfides (or diselenide) as chalcogenation reagents. High functional group tolerance and excellent regioselectivity are demonstrated by the efficient preparation of a wide range ofortho-sulfenylation-7-azaindoles.

Syntheses of 1-aryl-5-nitro-1h-indazoles and a general one-pot route to 1-aryl-1h-indazoles

An efficient route to substituted 1-aryl-1H-indazoles has been developed and optimized. The method involved the preparation of arylhydrazones from acetophenone or benzaldehyde substituted by fluorine at C2 and nitro at C5, followed by deprotonation and nucleophilic aromatic substitution (SNAr) ring closure in 45–90%. Modification of this procedure to a one-pot domino process was successful in the acetophenone series (73–96%), while the benzaldehyde series (63–73%) required a step-wise addition of reagents. A general one-pot protocol for 1-aryl-1H-indazole formation without the limiting substitution patterns required for the SNAr cyclization has also been achieved in 62–78% yields. A selection of 1-aryl-1H-indazoles was prepared in high yield by a procedure that requires only a single laboratory operation.

Copper(I) salt/PEG-400 catalysis in one-pot direct synthesis of 1-aryl-1H-indazoles from 2-bromobenzaldehydes and arylhydrazines

2-Bromobenzaldehydes are condensed and cyclized with arylhydrazines (or their hydrochlorides) in PEG-400 at 110 °C in the presence of a catalytic amount of a copper(I) salt along with a base to give 1-aryl-1H-indazoles in high yields. Copyright 2013 John Wiley & Sons, Ltd. Condensation of 2-bromobenzaldehydes with arylhydrazines (or their hydrochlorides) followed by C-N bond formation in PEG-400 in the presence of a copper(I) salt along with a base affords 1-aryl-1H-indazoles. Copyright

Synthesis of 1-aryl-1H-indazoles via a ligand-free copper-catalyzed intramolecular amination reaction

A general synthesis of 1-aryl-1-H-indazoles from o-halogenated aryl aldehydes or ketones and aryl hydrazines was described. This protocol included an intermolecular condensation and a ligand-free copper-catalyzed intramolecular Ullmann-type coupling react

Synthesis of N-arylindazoles and benzimidazoles from a common intermediate

A variety of N-aryl-1H-indazoles and benzimidazoles were synthesized from common arylamino oximes in good to excellent yields. The product selectivity depends upon the base used in the reaction, as triethylamine promoted the formation of benzimidazoles, whereas 2-aminopyridine promoted the formation of N-arylindazoles. This method is valuable to the synthetic community because both indazoles and benzimidazoles are prevalent in pharmaceuticals.

Efficient synthesis of 1-aryl-1H-indazole derivatives via copper(I)-catalyzed intramolecular amination reaction

A copper(I)-catalyzed intramolecular amination reaction using CuI, KOH, and 1,4-dioxane at 105°C for the preparation of 1-aryl-1H-indazole derivatives was described. The method was applied to a wide scope of substrates and afforded indazole products in hi

Microwave-assisted synthesis of 1-aryl-1H-indazoles via one-pot two-step Cu-catalyzed intramolecular N-arylation of arylhydrazones

A highly efficient one-pot two-step microwave procedure was developed for the synthesis of 1-aryl-1H-indazoles. Microwave heating of 2-halobenzaldehydes or 2-haloacetophenones with phenylhydrazines at 160°C for 10 min quantitatively yielded the arylhydraz