structure of 6-Nitro-1H-pyrrolo[3,2-c]pyridine

6-Nitro-1H-pyrrolo[3,2-c]pyridine

CAS No.: 1000342-77-7
M. Wt: 163.133
M. Fa: C7H5N3O2
InChI Key: NKDYJOFWMSSDFZ-UHFFFAOYSA-N

Names and Identifiers of 6-Nitro-1H-pyrrolo[3,2-c]pyridine

CAS Number

1000342-77-7

MDL Number

MFCD08690137

IUPAC Name

6-nitro-1H-pyrrolo[3,2-c]pyridine

InChI

InChI=1S/C7H5N3O2/c11-10(12)7-3-6-5(4-9-7)1-2-8-6/h1-4,8H

InChIKey

NKDYJOFWMSSDFZ-UHFFFAOYSA-N

Canonical SMILES

C1=CNC2=CC(=NC=C21)[N+](=O)[O-]

UNSPSC Code

12352100

Physical and chemical properties of 6-Nitro-1H-pyrrolo[3,2-c]pyridine

Acidity coefficient

12.96±0.40(Predicted)

Boiling Point

437.6±25.0 °C at 760 mmHg

Density

1.5±0.1 g/cm3

Exact Mass

163.038177

Flash Point

218.5±23.2 °C

H Bond Acceptors

3

H Bond Donors

1

Index of Refraction

1.741

LogP

0.44

Molecular Formula

C7H5N3O2

Molecular Weight

163.133

PSA

74.50000

Vapour Pressure

0.0±1.0 mmHg at 25°C

Safety Information of 6-Nitro-1H-pyrrolo[3,2-c]pyridine

Pictograms

Signal Word

 Warning

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

Applications of 6-Nitro-1H-pyrrolo[3,2-c]pyridine

The primary applications of 6-Nitro-1H-pyrrolo[3,2-c]pyridine are in medicinal chemistry and drug discovery:

  • As a building block for synthesizing more complex molecules with potential pharmacological activities.
  • In the development of kinase inhibitors, particularly those targeting FMS kinase.
  • As a scaffold for creating libraries of compounds for high-throughput screening in drug discovery programs.

Interaction Studies of 6-Nitro-1H-pyrrolo[3,2-c]pyridine

The interactions of 6-Nitro-1H-pyrrolo[3,2-c]pyridine with biological targets, particularly kinases, are of significant interest:

FMS Kinase: Derivatives of this compound have shown interactions with Fibroblast Growth Factor Receptors (FGFRs), affecting the FGF-FGFR axis. This interaction can lead to changes in cell proliferation, migration, and angiogenesis.

Similar Compounds

Several compounds share structural similarities with 6-Nitro-1H-pyrrolo[3,2-c]pyridine:

  • 1H-Pyrrolo[2,3-b]pyridine: This isomer differs in the position of the nitrogen atom in the pyrrole ring.
  • 1H-Pyrrolo[3,4-c]pyridine: Another isomer with a different fusion pattern of the pyridine and pyrrole rings.
  • 3-Nitro-1H-pyrrolo[3,2-c]pyridine: This compound differs only in the position of the nitro group.
  • 6-Methoxy-3-nitro-1H-pyrrolo[3,2-c]pyridine: A related compound with an additional methoxy group.
  • 6-Chloro-3-nitro-1H-pyrrolo[2,3-b]pyridine: This compound has a chloro substituent instead of the nitro group at the 6-position and a different ring fusion pattern.

The uniqueness of 6-Nitro-1H-pyrrolo[3,2-c]pyridine lies in its specific substitution pattern, which contributes to its particular biological activities and reactivity profile. The position of the nitro group at C-6 distinguishes it from many of its isomers and analogs, potentially leading to different interactions with biological targets and distinct chemical properties.

Biological Activity of 6-Nitro-1H-pyrrolo[3,2-c]pyridine

6-Nitro-1H-pyrrolo[3,2-c]pyridine and its derivatives have shown promising biological activities, particularly in the field of cancer research:

Kinase Inhibition: Some derivatives of this compound have demonstrated inhibitory effects against FMS kinase, which is involved in various cellular processes and has been implicated in certain types of cancer.

Antiproliferative Effects: In vitro studies have shown that certain derivatives can inhibit breast cancer 4T1 cell proliferation and induce apoptosis.