structure of 5-Bromo-6-methyl-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde

5-Bromo-6-methyl-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde

CAS No.: 1000343-91-8
M. Wt: 239.069
M. Fa: C9H7BrN2O
InChI Key: HHBZEJKHKKWZHN-UHFFFAOYSA-N

Names and Identifiers of 1000343-91-8

CAS Number

1000343-91-8

MDL Number

MFCD09880099

IUPAC Name

5-bromo-6-methyl-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde

InChI

InChI=1S/C9H7BrN2O/c1-5-8(10)2-7-6(4-13)3-11-9(7)12-5/h2-4H,1H3,(H,11,12)

InChIKey

HHBZEJKHKKWZHN-UHFFFAOYSA-N

Canonical SMILES

CC1=C(C=C2C(=CNC2=N1)C=O)Br

UNSPSC Code

12352100

Physical and chemical properties of 1000343-91-8

Density

1.7±0.1 g/cm3

Exact Mass

237.974167

H Bond Acceptors

2

H Bond Donors

1

Index of Refraction

1.736

LogP

2.70

Molecular Formula

C9H7BrN2O

Molecular Weight

239.069

PSA

45.75000

Storage condition

2-8°C

Safety Information of 1000343-91-8

Pictograms

Signal Word

 Warning

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

Applications of 1000343-91-8

5-Bromo-6-methyl-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde has applications in medicinal chemistry as a potential therapeutic agent targeting FGFRs in various cancers. Its unique structure allows for further modifications that could enhance its biological activity and specificity. Additionally, it serves as an intermediate in organic synthesis for developing other biologically active compounds .

Interaction Studies of 1000343-91-8

Studies have demonstrated that 5-Bromo-6-methyl-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde interacts specifically with FGFRs through hydrogen bonding and hydrophobic interactions. These interactions are critical for its inhibitory effects on cancer cell proliferation. The compound's ability to bind effectively to FGFRs highlights its potential as a lead compound for developing novel anti-cancer therapies targeting aberrant FGFR signaling pathways .

Biological Activity of 1000343-91-8

The compound exhibits significant biological activity, particularly as an inhibitor of fibroblast growth factor receptors (FGFRs). These receptors are crucial in cell signaling pathways that regulate proliferation, differentiation, and survival. In studies involving cancer cell lines, such as breast cancer 4T1 cells, 5-Bromo-6-methyl-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde has been shown to inhibit cell proliferation and induce apoptosis. Its mechanism involves direct binding to FGFRs, forming hydrogen bonds with key amino acids in their active sites, thereby inhibiting their function .