252722-30-8

Basic information

• Product Name: N-cyclohexyl-N-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine
• Synonyms: N-cyclohexyl-N-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine
• CAS NO: 252722-30-8
• Molecular Weight: 230.313
• Mol File: 252722-30-8.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: N-cyclohexyl-N-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine(CAS DataBase Reference)
• NIST Chemistry Reference: N-cyclohexyl-N-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine(252722-30-8)
• EPA Substance Registry System: N-cyclohexyl-N-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine(252722-30-8)

Safety Data

• Hazardous Substances Data: 252722-30-8(Hazardous Substances Data)

Upstream product

• 100-60-7 N-methylcyclohexylamine 
• 3680-69-1 4-chloro-1H-pyrrolo[2,3-d]pyrimidine 

Relevant articles and documents

Novel Hinge-Binding Motifs for Janus Kinase 3 Inhibitors: A Comprehensive Structure-Activity Relationship Study on Tofacitinib Bioisosteres

The Janus kinases (JAKs) are a family of cytosolic tyrosine kinases crucially involved in cytokine signaling. JAKs have been demonstrated to be valid targets in the treatment of inflammatory and myeloproliferative disorders, and two inhibitors, tofacitinib and ruxolitinib, recently received their marketing authorization. Despite this success, selectivity within the JAK family remains a major issue. Both approved compounds share a common 7H-pyrrolo[2,3-d]pyrimidine hinge binding motif, and little is known about modifications tolerated at this heterocyclic core. In the current study, a library of tofacitinib bioisosteres was prepared and tested against JAK3. The compounds possessed the tofacitinib piperidinyl side chain, whereas the hinge binding motif was replaced by a variety of heterocycles mimicking its pharmacophore. In view of the promising expectations obtained from molecular modeling, most of the compounds proved to be poorly active. However, strategies for restoring activity within this series of novel chemotypes were discovered and crucial structure-activity relationships were deduced. The compounds presented may serve as starting point for developing novel JAK inhibitors and as a valuable training set for in silico models.

Monocyclic-7H-pyrrolo[2,3-d]pyrimidine compounds, compositions, and methods of use

Novel pyrrolo[2,3-d]pyrimidine compounds useful as inhibitors of the enzyme protein tyrosine kinases such as Janus Kinase 3 as well as immunosuppressive agents for organ transplants, lupus, multiple sclerosis, rheumatoid arthritis, psoriasis, Type I diabetes and complications from diabetes, cancer, asthma, atopic dermatitis, autoimmune thyroid disorders, ulcerative colitis, Crohn's disease, Alzheimer's disease, Leukemia and other autoimmune diseases are described.