4-Chloro-1h-pyrrolo[2,3-b]pyridine-3-carbaldehyde (918515-16-9)
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Description
Janus kinases (JAKs) play a crucial role in cytokine mediated signal transduction. JAK inhibitors have emerged as effective immunomodulative agents for the prevention of transplant rejection. We previously reported that the tricyclic imidazo-pyrrolopyridinone 2 is a potent JAK inhibitor; however, it had poor oral absorption due to low membrane permeability. Here, we report the structural modification of compound 2 into the tricyclic dipyrrolopyridine 18a focusing on reduction of polar surface area (PSA), which exhibits potent in vitro activity, improved membrane permeability and good oral bioavailability. Compound 18a showed efficacy in rat heterotopic cardiac transplants model.
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4-Chloro-1h-pyrrolo[2,3-b]pyridine-3-carbaldehyde (918515-16-9) Specifications
CAS | 918515-16-9 |
CAS Min % | 95% |
CAS Max % | 100% |
MDL Number | MFCD09880129 |
InChI Key | DYWWVLQMUUZZRJ-UHFFFAOYSA-N |
Chemical Name or Material | 4-Chloro-1h-pyrrolo[2,3-b]pyridine-3-carbaldehyde |
Infrared Spectrum | Authentic |
Physical Form | White to brown solid |
Packaging | Glass bottle |
Molecular Formula | C8H5N2OCl |
Molecular Weight (g/mol) | 180.594 |
SMILES | ClC1(=C2(C(=NC=C1)NC=C2C=O)) |
Color | White |
Boiling Point | 372.6 °C at 760 mmHg |
Assay | 98% |
4-Chloro-1h-pyrrolo[2,3-b]pyridine-3-carbaldehyde (918515-16-9) Safety and Handling
- Do not breath dust or vapor.
- Have safety shower and eye wash available.
- Do not get in eyes, on skin or on clothing.
- Keep container tightly closed.
- Store in a cool, dry, well-ventilated place.
- Ensure adequate ventilation during use.
- Use only in a chemical fume hood.
WARNING: The information provided on this web site was developed in compliance with European Union (EU) regulations and is correct to the best of our knowledge, information and belief at the date of its publication. The information given is designed only as a guide for safe handling and use. It is not to be considered as either a warranty or quality specification.
4-Chloro-1h-pyrrolo[2,3-b]pyridine-3-carbaldehyde (918515-16-9) Articles
Discovery of tricyclic dipyrrolopyridine derivatives as novel JAK inhibitors
Janus kinases (JAKs) play a crucial role in cytokine mediated signal transduction. JAK inhibitors have emerged as effective immunomodulative agents for the prevention of transplant rejection.
Bioorganic and Medicinal Chemistry 2017
Synthesis and biological evaluation of pyrrolo[2,3-b]pyridine analogues as antiproliferative agents and their interaction with calf thymus DNA
A series of thirty two novel pyrrolo[2,3-b]pyridine analogues synthesized, characterized (1H NMR, 13C NMR and MS) and cytotoxic evaluation of these molecules carried out over a panel of three human cancer cell lines including A549
European Journal of Medicinal Chemistry 2016
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