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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