structure of 1H-pyrrolo[2,3-b]pyridine-3-sulfonyl chloride

1H-pyrrolo[2,3-b]pyridine-3-sulfonyl chloride

CAS No.: 1001412-59-4
M. Wt: 216.64500
M. Fa: C7H5ClN2O2S
InChI Key: CNZIHLRMHLLIJQ-UHFFFAOYSA-N
Appearance: Pale-yellow Solid

Names and Identifiers of 1001412-59-4

CAS Number

1001412-59-4

EC Number

862-450-1

MDL Number

MFCD12402502

IUPAC Name

1H-pyrrolo[2,3-b]pyridine-3-sulfonyl chloride

InChI

InChI=1S/C7H5ClN2O2S/c8-13(11,12)6-4-10-7-5(6)2-1-3-9-7/h1-4H,(H,9,10)

InChIKey

CNZIHLRMHLLIJQ-UHFFFAOYSA-N

Canonical SMILES

C1=CC2=C(NC=C2S(=O)(=O)Cl)N=C1

UNSPSC Code

12352100

Physical and chemical properties of 1001412-59-4

Density

1.7

Exact Mass

215.97600

H Bond Acceptors

3

H Bond Donors

1

LogP

2.57120

Molecular Formula

C7H5ClN2O2S

Molecular Weight

216.64500

PSA

71.20000

Safety Information of 1001412-59-4

Pictograms

Signal Word

 Danger

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

Applications of 1001412-59-4

This compound has several applications in medicinal chemistry and biochemistry:

  • Drug Development: Due to its ability to inhibit specific enzymes and cellular processes, it serves as a lead compound for developing new anticancer agents.
  • Biochemical Research: It is utilized in proteomics research for studying protein interactions and enzyme functions.
  • Synthetic Chemistry: As a versatile sulfonylating agent, it is employed in various organic synthesis applications to create sulfonamide derivatives.

Interaction Studies of 1001412-59-4

Research has focused on understanding the interactions between 1H-pyrrolo[2,3-b]pyridine-3-sulfonyl chloride and biological targets. Studies indicate that it effectively inhibits FGFRs, which are crucial for numerous cellular processes including growth and differentiation. The compound's interaction profile suggests potential for use in targeted therapies against cancers that exhibit aberrant FGFR signaling.

Biological Activity of 1001412-59-4

1H-pyrrolo[2,3-b]pyridine-3-sulfonyl chloride exhibits significant biological activity, particularly in the realm of cancer research. It has been shown to inhibit the proliferation of various cancer cell lines, including 4T1 (mouse breast cancer cells), MDA-MB-231, and MCF-7 breast cancer cells. The compound interacts with fibroblast growth factor receptors (FGFRs), demonstrating potent inhibitory activity that may contribute to its anticancer properties.

Molecular Mechanism

The mechanism of action involves binding interactions with biomolecules, specifically targeting the FGFR1 hinge region through hydrogen bonding. This interaction disrupts normal signaling pathways that promote cell proliferation and survival, leading to reduced cancer cell viability.

Physical sample testing spectrum (NMR) of 1001412-59-4

Physical sample testing spectrum (NMR) of 1001412-59-4

Retrosynthesis analysis of 1001412-59-4

  • Route#1

    Cas:271-63-6
    Cas:1001412-59-4