structure of 2H-Pyrrolo[2,3-d]pyrimidin-2-one, 4-amino-1,7-dihydro- (9CI)

2H-Pyrrolo[2,3-d]pyrimidin-2-one, 4-amino-1,7-dihydro- (9CI)

CAS No.: 100047-45-8
M. Wt: 150.13800
M. Fa: C6H6N4O
InChI Key: IJOIJRLXVJYPIF-UHFFFAOYSA-N

Names and Identifiers of 100047-45-8

CAS Number

100047-45-8

MDL Number

MFCD35098241

IUPAC Name

4-amino-2H,3H,7H-pyrrolo[2,3-d]pyrimidin-2-one

InChI

InChI=1S/C6H6N4O/c7-4-3-1-2-8-5(3)10-6(11)9-4/h1-2H,(H4,7,8,9,10,11)

InChIKey

IJOIJRLXVJYPIF-UHFFFAOYSA-N

Canonical SMILES

NC1=C2C=CNC2=NC(=O)N1

UNSPSC Code

12352100

Physical and chemical properties of 100047-45-8

Exact Mass

150.05400

H Bond Acceptors

4

H Bond Donors

3

Index of Refraction

1.89

LogP

0.82690

Molecular Formula

C6H6N4O

Molecular Weight

150.13800

PSA

87.82000

Storage condition

2-8°C

Safety Information of 100047-45-8

Pictograms

Signal Word

 Warning

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

Applications of 100047-45-8

The unique properties of 4-amino-1H-pyrrolo[2,3-d]pyrimidin-2(3H)-one make it valuable in several fields:

  • Pharmaceuticals: Its potential as an antihyperglycemic agent and kinase inhibitor positions it as a candidate for drug development against diabetes and malaria.
  • Material Science: The compound may also find applications in developing new materials due to its heterocyclic structure.

Interaction Studies of 100047-45-8

Studies focusing on the interactions of 4-amino-1H-pyrrolo[2,3-d]pyrimidin-2(3H)-one with biological targets have revealed its potential mechanisms of action:

  • Kinase Binding Studies: Molecular docking studies have shown how derivatives can fit into kinase active sites, providing insights into their inhibitory mechanisms against specific kinases involved in disease processes.
  • Biochemical Assays: In vitro assays have confirmed the biological activity of these compounds, supporting their role as potential therapeutic agents.

Biological Activity of 100047-45-8

Research indicates that 4-amino-1H-pyrrolo[2,3-d]pyrimidin-2(3H)-one and its derivatives exhibit significant biological activities. Notably:

  • Antihyperglycemic Activity: Some pyrrolopyrimidine derivatives have been evaluated for their potential to lower blood glucose levels in animal models, suggesting therapeutic applications in diabetes management.
  • Inhibitory Activity Against Kinases: Compounds within this class have been designed to inhibit specific kinases such as Plasmodium falciparum calcium-dependent protein kinase 4 (PfCDPK4), which is crucial for malaria treatment strategies. Some derivatives showed promising inhibitory activity with IC50 values in the low micromolar range.