structure of 4-Cyano-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid

4-Cyano-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid

CAS No.: 1000340-46-4
M. Wt: 187.155
M. Fa: C9H5N3O2
InChI Key: RMWDOEYDAZDORR-UHFFFAOYSA-N

Names and Identifiers of 1000340-46-4

CAS Number

1000340-46-4

MDL Number

MFCD09880139

IUPAC Name

4-cyano-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid

InChI

InChI=1S/C9H5N3O2/c10-3-5-1-2-11-8-7(5)6(4-12-8)9(13)14/h1-2,4H,(H,11,12)(H,13,14)

InChIKey

RMWDOEYDAZDORR-UHFFFAOYSA-N

Canonical SMILES

C1=CN=C2C(=C1C#N)C(=CN2)C(=O)O

UNSPSC Code

12352100

Physical and chemical properties of 1000340-46-4

Boiling Point

427.9±40.0 °C at 760 mmHg

Density

1.6±0.1 g/cm3

Exact Mass

187.038177

Flash Point

212.6±27.3 °C

H Bond Acceptors

4

H Bond Donors

2

Index of Refraction

1.729

LogP

2.44

Molecular Formula

C9H5N3O2

Molecular Weight

187.155

PSA

89.77000

Storage condition

2-8°C

Vapour Pressure

0.0±1.1 mmHg at 25°C

Safety Information of 1000340-46-4

Pictograms

Signal Word

 Warning

Safety Data Sheet
Supports customized editing of SDS information and downloading in PDF documents.

Applications of 1000340-46-4

4-Cyano-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid has several potential applications:

  • Pharmaceutical Development: Its derivatives are being investigated as potential anticancer agents due to their ability to inhibit key signaling pathways involved in tumor growth.
  • Biochemical Research: This compound serves as a useful tool for studying enzyme inhibition and cellular signaling mechanisms.
  • Material Science: Its unique structure may be explored for developing advanced materials with specific electronic or optical properties.

Interaction Studies of 1000340-46-4

Studies on the interactions of 4-cyano-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid with biological targets have revealed:

  • Binding Affinity: Some derivatives exhibit high binding affinity for FGFRs and other kinases, indicating their potential as therapeutic agents .
  • Mechanism of Action: Investigations into their mechanism of action suggest that these compounds may disrupt critical signaling pathways in cancer cells, leading to reduced cell viability and increased apoptosis.

These findings underline the importance of further research into their pharmacodynamics and pharmacokinetics.

Biological Activity of 1000340-46-4

Research indicates that derivatives of 4-cyano-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid exhibit significant biological activities. Notably:

  • Inhibition of Fibroblast Growth Factor Receptors: Some derivatives have shown potent inhibitory effects against fibroblast growth factor receptors (FGFRs), which are implicated in various cancers. For instance, certain compounds have demonstrated IC₅₀ values in the nanomolar range against FGFR1, 2, and 3 .
  • Antitumor Activity: In vitro studies suggest that these compounds can inhibit cell proliferation and induce apoptosis in cancer cell lines .
  • Kinase Inhibition: Compounds related to this structure have been explored as inhibitors of specific kinases involved in cancer progression .