10299-55-5

Usage

Uses

Used in Pharmaceutical Industry:
3-Phenyl-7-azaindole is used as a ligand for the serotonin 5-HT6 receptor, playing a crucial role in the development of drugs targeting this receptor for the treatment of neurological and psychiatric disorders.
Used in Organic Synthesis:
3-Phenyl-7-azaindole is utilized as a building block for the synthesis of pharmaceutical compounds, contributing to the creation of novel therapeutic agents with improved efficacy and selectivity.
Used in Optoelectronic Industry:
3-Phenyl-7-azaindole is employed in the development of organic light-emitting diodes (OLEDs) and other optoelectronic applications, owing to its unique electronic and optical properties.
Further research on the properties and applications of 3-Phenyl-7-azaindole is ongoing, with the potential to uncover additional uses in various fields.

Upstream product

• 74420-15-8 3-bromo-1H-pyrrolo[2,3-b]pyridine 
• 226085-18-3 3-bromo-1-(4-methylbenzenesulfonyl)-1H-pyrrolo[2,3-b]pyridine 
• 54231-33-3 3-bromo-2-nitropyridine 
• 4545-21-5 acetophenone p-toluenesulfonylhydrazone 
• 271-63-6 7-Azaindole 
• 98-80-6 phenylboronic acid 
• 1311484-52-2 MIDA alkenyl-2-boronate 
• 100-63-0 phenylhydrazine 

Relevant academic research and scientific papers

A palladium-catalyzed Barluenga cross-coupling – Reductive cyclization sequence to substituted indoles

A short and flexible synthesis of substituted indoles employing two palladium-catalyzed reactions, a Barluenga cross-coupling of p-tosylhydrazones with 2-nitroarylhalides followed by a palladium–catalyzed, carbon monoxide–mediated reductive cyclization has been developed. A one-pot, two-step methodology was further developed, eliminating isolation and purification of the cross-coupling product. This was accomplished by utilizing the initially added 0.025 equivalents of bis(triphenylphosphine)palladium dichloride, thus serving a dual role in the cross-coupling and the reductive cyclization. It was found that addition of 1,3-bis(diphenylphosphino)propane and carbon monoxide after completion of the Barluenga reaction afforded, in most cases, significantly better overall yields.

Discovery of a novel class of covalent dual inhibitors targeting the protein kinases bmx and btk

The nonreceptor tyrosine TEC kinases are key regulators of the immune system and play a crucial role in the pathogenesis of diverse hematological malignancies. In contrast to the substantial efforts in inhibitor development for Bruton’s tyrosine kinase (BTK), specific inhibitors of the other TEC kinases, including the bone marrow tyrosine kinase on chromosome X (BMX), remain sparse. Here we present a novel class of dual BMX/BTK inhibitors, which were designed from irreversible inhibitors of Janus kinase (JAK) 3 targeting a cysteine located within the solvent-exposed front region of the ATP binding pocket. Structure-guided design exploiting the differences in the gatekeeper residues enabled the achievement of high selectivity over JAK3 and certain other kinases harboring a sterically demanding residue at this position. The most active compounds inhibited BMX and BTK with apparent IC50 values in the single digit nanomolar range or below showing moderate selectivity within the TEC family and potent cellular target engagement. These compounds represent an important first step towards selective chemical probes for the protein kinase BMX.

Synthesis method of palladium-catalyzed 3-aryl 7-azaindole compound

A synthesis method of a palladium-catalyzed 3-aryl 7-azaindole compound comprises the following steps: adding a 7-azaindole compound and an arylboronic acid compound into a reaction tube, adding a transition metal palladium catalyst, an oxidizing agent, alkali and a solvent, and reacting at 40-100 DEG C for 2-24 hours to obtain the 3-aryl 7-azaindole compound. In the invention, the reaction systemdoes not need additional addition of N-containing and P-containing ligands; the N1-site protective group in the 7-azaindole compound is not important, whether the N1-site protective group exists or not has no obvious influence on the activity and selectivity of the arylation reaction, and the reaction can selectively occur at the C3 site of the 7-azaindole compound; the arylboronic acid compoundis used as an arylation reagent, so that toxicity is obviously reduced, and high-pollution halides cannot be generated in the reaction process; the whole reaction process is simple, efficient, low intoxicity and convenient to operate.

A general synthesis of arylindoles and (1-arylvinyl)carbazoles: Via a one-pot reaction from N -tosylhydrazones and 2-nitro-haloarenes and their potential application to colon cancer

A convergent and effective synthesis of 3-aryl-indoles, 2,3-diaryl indoles, and (1-arylvinyl)carbazoles from a one-pot sequence involving the coupling of N-tosylhydrazones with ortho-nitro-haloarenes followed by a cyclization has been developed. Compound 5i exhibits excellent antiproliferative activity in the low nM range against colon cancer cell lines.

Vinylic MIDA boronates: New building blocks for the synthesis of aza-heterocycles

Abstract A two-step synthesis of structurally diverse pyrrole-containing bicyclic systems is reported. ortho-Nitro-haloarenes coupled with vinylic N-methyliminodiacetic acid (MIDA) boronates generate ortho-vinyl-nitroarenes, which undergo a "metal-free" nitrene insertion, resulting in a new pyrrole ring. This novel synthetic approach has a wide substrate tolerance and it is applicable in the preparation of more complex "drug-like" molecules. Interestingly, an ortho-nitro-allylarene derivative furnished a cyclic β-aminophosphonate motif. Old dog, new tricks: A two-step synthesis of structurally diverse pyrrole-containing bicyclic systems is reported. ortho-Nitro-haloarenes coupled with vinylic N-methyliminodiacetic acid (MIDA) boronates generate ortho-vinyl-nitroarenes, which undergo a "metal-free" nitrene insertion, resulting in a new pyrrole ring. This approach has a wide substrate tolerance and it is applicable in the preparation of more complex "drug-like" molecules. Interestingly, an ortho-nitro-allylarene derivative furnished a cyclic β-aminophosphonate motif.

Palladium-catalyzed direct denitrogenative C-3-arylation of 1H-indoles with arylhydrazines using air as the oxidant

A novel palladium-catalyzed approach to direct C-3-arylation of 1H-indoles with arylhydrazines using air as the oxidant via C-N bond cleavage has been developed. Various substituents are tolerated in this system in moderate to good yields. This reaction could also be compatible with a larger scale. Thus, this strategy using arylhydrazines as arylating reagents provides a powerful method for constructing substituted 3-aryl-1H-indoles. Copyright

CB1 MODULATOR COMPOUNDS

Novel compounds of structural formula (I) are disclosed. As modulators of the Cannabinoid-1 (CB1) receptor, these compounds are useful in the treatment, prevention and suppression of diseases mediated by the CB1 receptor. As such, compounds of the present invention are useful as in the treatment, prevention and suppression of psychosis, memory deficits, cognitive disorders, migraine, neuropathy, neuro-inflammatory disorders (e.g., multiple sclerosis, Guillain-Barre syndrome and the inflammatory sequelae of viral encephalitis), cerebral vascular accidents, head trauma, anxiety disorders, stress, epilepsy, Parkinson's disease, and schizophrenia. The compounds are also useful for the treatment of substance abuse disorders, particularly to opiates, alcohol, and nicotine. The compounds are also useful for the treatment of obesity or eating disorders associated with excessive food intake and complications associated therewith.