611205-38-0

Basic information

• Product Name: 1H-Pyrrolo[2,3-b]pyridine, 5-phenyl-
• CAS NO: 611205-38-0
• Molecular Formula: C13H10N2
• Molecular Weight: 194.236
• Mol File: 611205-38-0.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: 1H-Pyrrolo[2,3-b]pyridine, 5-phenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Pyrrolo[2,3-b]pyridine, 5-phenyl-(611205-38-0)
• EPA Substance Registry System: 1H-Pyrrolo[2,3-b]pyridine, 5-phenyl-(611205-38-0)

Safety Data

• Hazardous Substances Data: 611205-38-0(Hazardous Substances Data)

Usage

Heterocyclic aromatic compound

This term refers to the fact that the compound consists of a pyrrole ring fused to a pyridine ring, both of which are heterocyclic (containing atoms other than carbon) and aromatic (having a stable, delocalized electron structure).

Pyrrole ring

This is a five-membered ring with four carbon atoms and one nitrogen atom, which is a common structural motif in organic chemistry.

Pyridine ring

This is a six-membered ring with five carbon atoms and one nitrogen atom, which is also a common structural motif in organic chemistry.

Phenyl group

This is a group consisting of a six-membered ring of carbon atoms with delocalized electrons, which is commonly found in organic compounds.

Attached at the 5-position

This indicates the location of the phenyl group on the pyridine ring, which is at the fifth position (counting from the nitrogen atom in the pyridine ring).

Building block in the synthesis of pharmaceuticals and organic compounds

This term refers to the fact that 1H-Pyrrolo[2,3-b]pyridine, 5-phenylis commonly used as an intermediate in the synthesis of other compounds, particularly in the pharmaceutical industry.

Potential applications in drug discovery and development

This term refers to the fact that 1H-Pyrrolo[2,3-b]pyridine, 5-phenylhas unique structural properties and biological activities that make it a promising candidate for the development of new drugs.

Fluorescent probe in biological imaging

This term refers to the fact that 1H-Pyrrolo[2,3-b]pyridine, 5-phenylhas been studied for its potential use as a probe in biological imaging, which involves using fluorescent compounds to visualize and study biological processes.

Component in organic electronic devices

This term refers to the fact that 1H-Pyrrolo[2,3-b]pyridine, 5-phenylhas been studied for its potential use in organic electronic devices, such as organic light-emitting diodes (OLEDs) and organic solar cells.

Upstream product

• 1001070-33-2 1-(benzenesulfonyl)-5-bromo-1H-pyrrolo[2,3-b]pyridine 
• 183208-35-7 5-bromo-1H-pyrrolo[2,3-b]pyridine 
• 98-80-6 phenylboronic acid 
• 108-86-1 bromobenzene 
• 24388-23-6 2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole 

Downstream Products

• 1261435-99-7 5-phenyl-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde 
• 1163302-94-0 1-(2-fluoro-5-(trifluoromethyl)phenyl)-3-(3-(5-phenyl-1H-pyrrolo[2,3-b]pyridin-3-yl)phenyl)urea 
• 890839-39-1 3-bromo-1-[(4-methylphenyl)sulfonyl]-5-phenyl-1H-pyrrolo[2,3-b]pyridine 
• 890928-21-9 3-bromo-5-phenyl-1H-pyrrolo[2,3-b]pyridine 

Relevant articles and documents

Synthesis and biological evaluation of selected 7-azaindole derivatives as CDK9/Cyclin T and Haspin inhibitors

The 7-azaindole scaffold attracts attention due to its value in the design of inhibitors of diseases related protein kinases. However, this scaffold has not been evaluated against Haploid germ cell-specific nuclear protein kinase (Haspin). Herein, we report the synthesis of a select set of 7-azaindole derivatives and their evaluation against Haspin. The compounds were also evaluated against CDK9/Cyclin T kinase. The synthesis of 7-azaindole derivatives was achieved through Suzuki coupling using appropriate halogenated 7-azaindole and boronic acids. Seven of the screened compounds exhibited activity as CDK9/Cyclin T and/or Haspin inhibitors in a nanomolar to low micromolar range. The most promising dual inhibiting compound 18c, exhibited an inhibitory potential of 0.206 μM against CDK9/Cyclin T and 0.118 μM against Haspin. The dual inhibition of CDK9/Cyclin T and Haspin could afford a potentially potent antimitotic agent of value in further anticancer studies.

Virtual Screening Identifies Irreversible FMS-like Tyrosine Kinase 3 Inhibitors with Activity toward Resistance-Conferring Mutations

The use of covalent irreversible binding inhibitors is an established concept for drug development. Usually, the discovery of new irreversible kinase inhibitors occurs serendipitously, showing that efficient rational approaches for the rapid discovery of new drugs are needed. Herein, we report a virtual screening strategy that led to the discovery of irreversible inhibitors of FMS-like tyrosine kinase 3 (FLT3) involved in the pathogenesis of acute myeloid leukemia. A virtual screening library was designed to target the highly conserved Cys828 residue preceding the DFG motif by modification of reported reversible inhibitors with chemically reactive groups. Prospective covalent docking allowed the identification of two lead series, resulting in a massive increase in inhibition of kinase activity and cell viability by irreversible inhibitors compared to the corresponding reversible scaffolds. Lead compound 4b (BSc5371) displays superior cytotoxicity in FLT3-dependent cell lines to compounds in recent clinical trials and overcomes drug-resistant mutations.

Discovery of small molecule RIP1 kinase inhibitors for the treatment of pathologies associated with necroptosis

Potent inhibitors of RIP1 kinase from three distinct series, 1-aminoisoquinolines, pyrrolo[2,3-b]pyridines, and furo[2,3-d]pyrimidines, all of the type II class recognizing a DLG-out inactive conformation, were identified from screening of our in-house ki