153374-33-5

Basic information

• Product Name: 1H-Pyrrolo[3,2-b]pyridine,1-methyl-(9CI)
• Synonyms: 1H-Pyrrolo[3,2-b]pyridine,1-methyl-(9CI);1-METHYL-1H-PYRROLO[3,2-B]PYRIDINE
• CAS NO: 153374-33-5
• Molecular Formula: C₈H₈N₂
• Molecular Weight: 132.165
• Product Categories: AMINETERTIARY;PYRIDINE
• Mol File: 153374-33-5.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1H-Pyrrolo[3,2-b]pyridine,1-methyl-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Pyrrolo[3,2-b]pyridine,1-methyl-(9CI)(153374-33-5)
• EPA Substance Registry System: 1H-Pyrrolo[3,2-b]pyridine,1-methyl-(9CI)(153374-33-5)

Safety Data

• Hazardous Substances Data: 153374-33-5(Hazardous Substances Data)

Usage

Heterocyclic compound

A compound that contains a ring of atoms with at least one atom being different from carbon, in this case, a pyrrole ring fused to a pyridine ring.

Pyrrole ring

A five-membered ring with four carbon atoms and one nitrogen atom, which is a part of the 1H-Pyrrolo[3,2-b]pyridine structure.

Pyridine ring

A six-membered ring with six carbon atoms, which is a part of the 1H-Pyrrolo[3,2-b]pyridine structure.

Methyl group

A chemical group consisting of one carbon atom and three hydrogen atoms, which is attached to the nitrogen atom of the pyrrole ring in 1H-Pyrrolo[3,2-b]pyridine,1-methyl-(9CI).

Biological activity

The ability of a compound to interact with biological targets such as enzymes or receptors, which is a potential application of 1H-Pyrrolo[3,2-b]pyridine,1-methyl-(9CI) in medicinal chemistry and drug development.

Building block

A simple molecule that can be used to synthesize more complex organic compounds, which is the role of 1H-Pyrrolo[3,2-b]pyridine,1-methyl-(9CI) in the synthesis of diverse organic compounds with various biological activities.

Derivative form

A version of a compound that has been modified by adding or removing functional groups, which can affect the specific uses and properties of 1H-Pyrrolo[3,2-b]pyridine,1-methyl-(9CI).

Upstream product

• 272-49-1 1H-pyrrolo[3,2-b]pyridine 
• 74-88-4 methyl iodide 
• 77-78-1 dimethyl sulfate 
• 123846-65-1 2-(3-nitropyridin-2-yl)acetonitrile 

Relevant articles and documents

Synthesis and antiproliferative activity of substituted 3[2-(1h-indol-3-yl)- 1,3-thiazol-4-yl]-1h-pyrrolo[3,2-b]pyridines, marine alkaloid nortopsentin analogues

A large number of indolyl-4-azaindolyl thiazoles, nortopsentin analogues, were conveniently synthesized. The antiproliferative activity of the new derivatives was examined against four human tumor cell lines with different histologic origin. Seven derivatives consistently reduced the growth of the experimental models independently of TP53 gene status and exhibited the highest activity against the malignant peritoneal mesothelioma (STO) cell line. The most active compound of this series acts as a CDK1 inhibitor, and was found to cause cell cycle arrest at G2/M phase, to induce apoptosis by preventing the phosphorylation of survivin in Thr34 and to increase the cytotoxic activity of paclitaxel in STO cells.

Site-selective azaindole arylation at the azine and azole rings via N-oxide activation

Subjection of N-methyl 6-and 7-azaindole N-oxides to a Pd(OAc) 2/DavePhos catalyst system enables regioselective direct arylation of the azine ring. Following deoxygenation, 7-azaindole substrates undergo an additional regioselective azole direct arylation event in good yield.

Structure-activity relationship of antiparasitic and cytotoxic indoloquinoline alkaloids, and their tricyclic and bicyclic analogues

Based on the indoloquinoline alkaloids cryptolepine (1), neocryptolepine (2), isocryptolepine (3) and isoneocryptolepine (4), used as lead compounds for new antimalarial agents, a series of tricyclic and bicyclic analogues, including carbolines, azaindoles, pyrroloquinolines and pyrroloisoquinolines was synthesized and biologically evaluated. None of the bicyclic compounds was significantly active against the chloroquine-resistant strain Plasmodium falciparum K1, in contrast to the tricyclic derivatives. The tricyclic compound 2-methyl-2H-pyrido[3,4-b]indole (9), or 2-methyl-β-carboline, showed the best in vitro activity, with an IC50 value of 0.45 μM against P. falciparum K1, without apparent cytotoxicity against L6 cells (SI > 1000). However, this compound was not active in the Plasmodium berghei mouse model. Structure-activity relationships are discussed and compared with related naturally occurring compounds.