1027236-75-4

Basic information

• Product Name: (7-Benzyl-5,6-dimethyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-(3-chloro-phenyl)-methyl-amine
• CAS NO: 1027236-75-4
• Molecular Weight: 376.889
• Mol File: 1027236-75-4.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (7-Benzyl-5,6-dimethyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-(3-chloro-phenyl)-methyl-amine(CAS DataBase Reference)
• NIST Chemistry Reference: (7-Benzyl-5,6-dimethyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-(3-chloro-phenyl)-methyl-amine(1027236-75-4)
• EPA Substance Registry System: (7-Benzyl-5,6-dimethyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-(3-chloro-phenyl)-methyl-amine(1027236-75-4)

Safety Data

• Hazardous Substances Data: 1027236-75-4(Hazardous Substances Data)

Upstream product

• 173458-77-0 7-benzyl-5,6-dimethyl-7H-pyrrolo[2,3-d]pyrimidin-4-ol 
• 55817-72-6 2-amino-1-benzyl-4,5-dimethyl-1H-pyrrole-3-carbonitrile 
• 7006-52-2 3-chloro-N-methylaniline 
• 173458-80-5 7-benzyl-4-chloro-5,6-dimethyl-7H-pyrrolo[2,3-d]pyrimidine 

Relevant articles and documents

4-(Phenylamino)pyrrolopyrimidines: Potent and selective, ATP site directed inhibitors of the EGF-receptor protein tyrosine kinase

Using a pharmacophore model for ATP-competitive inhibitors interacting with the active site of the EGF-R protein tyrosine kinase (PTK), 4- (phenylamino)-7H-pyrrolo[2,3-d]pyrimidines have been identified as a novel class of potent EGF-R protein tyrosine kinase inhibitors. In an interactive process, this class of compounds was then optimized. 13, 14, 28, 36, 37, and 44, the most potent compounds of this series, inhibited the EGF-R PTK with IC50 values in the low nanomolar range. High selectivity toward a panel of nonreceptor tyrosine kinases (c-Src, v-Abl) and serine/threonine kinases (PKC α, PKA) was observed. Kinetic analysis revealed competitive type kinetics relative to ATP. In cells, EGF-stimulated cellular tyrosine phosphorylation was inhibited by compounds 13, 36, 37, and 44 at IC50 values between 0.1 and 0.4 μM, whereas PDGF-induced tyrosine phosphorylation was not affected by concentrations up to 10 μM. In addition, these compounds were able to selectively inhibit c-fos mRNA expression in EGF-dependent cell lines with IC50 values between 0.1 and 2 μM, but did not affect c-fos mRNA induction in response to PDGF or PMA (IC50 >100 μM). Proliferation of the EGF- dependent MK cell line was inhibited with similar IC50 values. From SAR studies, a binding mode for 4-(phenylamino)-7H-pyrrolo[2,3-d]pyrimidines as well as for the structurally related 4-(phenylamino)quinazolines at the ATP- binding site of the EGF-R tyrosine kinase is proposed. 4-(Phenylamino)-7H- pyrrolo[2,3-d]pyrimidines therefore represent a new class of highly potent tyrosine kinase inhibitors which preferentially inhibit the EGF-mediated signal transduction pathway and have the potential for further evaluation as anticancer agents.