structure of 5-chloro-6-methyl-1H-pyrrolo[2,3-b]pyridin-3-amine

5-chloro-6-methyl-1H-pyrrolo[2,3-b]pyridin-3-amine

CAS No.: 1000340-14-6
M. Wt: 181.622
M. Fa: C8H8ClN3
InChI Key: -

Names and Identifiers of 1000340-14-6

CAS Number

1000340-14-6

IUPAC Name

5-chloranyl-6-methyl-1H-pyrrolo[2,3-b]pyridin-3-amine

Canonical SMILES

CC1=C(C=C2C(=CNC2=N1)N)Cl

Physical and chemical properties of 1000340-14-6

Density

1.4±0.1 g/cm3

Exact Mass

181.040680

Index of Refraction

1.738

LogP

2.21

Molecular Formula

C8H8ClN3

Molecular Weight

181.622

PSA

54.70000

Applications of 1000340-14-6

5-Chloro-6-methyl-1H-pyrrolo[2,3-b]pyridin-3-amine has several applications:

  • Pharmaceutical Development: It serves as a lead compound for developing FGFR inhibitors in cancer treatment.
  • Chemical Biology: The compound is used in studies investigating its interactions with biomolecules like DNA.
  • Synthetic Chemistry: It acts as an intermediate in synthesizing more complex heterocyclic compounds.

Interaction Studies of 1000340-14-6

Interaction studies have demonstrated that 5-Chloro-6-methyl-1H-pyrrolo[2,3-b]pyridin-3-amine can bind to target proteins involved in cell signaling pathways. Molecular docking simulations indicate that it can form hydrogen bonds and hydrophobic interactions with key residues in FGFRs, enhancing its potential as an anticancer agent. Furthermore, studies involving calf thymus DNA suggest that it may intercalate within DNA strands, affecting replication and transcription processes.

Biological Activity of 1000340-14-6

This compound exhibits significant biological activity, particularly as an inhibitor of fibroblast growth factor receptors (FGFRs). Abnormal activation of FGFR signaling pathways is implicated in various cancers, making this compound potentially useful in cancer therapy. Studies have shown that derivatives of pyrrolo[2,3-b]pyridine exhibit antiproliferative effects against tumor cell lines and may interact with DNA, suggesting potential applications in oncology as well as other therapeutic areas.