202579-59-7

Basic information

• Product Name: N-Butyl-N-[3-(2,4-dichlorophenyl)-2,5-dimethylpyrazolo[1,5-a]pyrimidin-7-yl]-N-ethylamine
• Synonyms: PD-171729
• CAS NO: 202579-59-7
• Molecular Formula: C₂₀H₂₄Cl₂N₄
• Molecular Weight: 391.34708
• Mol File: 202579-59-7.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: N-Butyl-N-[3-(2,4-dichlorophenyl)-2,5-dimethylpyrazolo[1,5-a]pyrimidin-7-yl]-N-ethylamine(CAS DataBase Reference)
• NIST Chemistry Reference: N-Butyl-N-[3-(2,4-dichlorophenyl)-2,5-dimethylpyrazolo[1,5-a]pyrimidin-7-yl]-N-ethylamine(202579-59-7)
• EPA Substance Registry System: N-Butyl-N-[3-(2,4-dichlorophenyl)-2,5-dimethylpyrazolo[1,5-a]pyrimidin-7-yl]-N-ethylamine(202579-59-7)

Safety Data

• Hazardous Substances Data: 202579-59-7(Hazardous Substances Data)

Upstream product

• 214416-34-9 3-(2,4-Dichloro-phenyl)-2,5-dimethyl-4H-pyrazolo[1,5-a]pyrimidin-7-one 
• 214416-40-7 5-amino-4-(2,4-dichlorophenyl)-3-methylpyrazole 
• 76562-15-7 1-cyano-1-(2,4-dichlorophenyl)propan-2-one 
• 6306-60-1 2,4-Dichlorophenylacetonitrile 
• 13360-63-9 N-ethylbutylamine 
• 948553-53-5 7-chloro-3-(2,4-dichlorophenyl)-2,5-dimethylpyrazolo[1,5-a]pyrimidine 

Relevant articles and documents

Synthesis, F-18 radiolabeling, and microPET evaluation of 3-(2,4-dichlorophenyl)-N-alkyl-N-fluoroalkyl-2,5-dimethylpyrazolo[1,5-a]pyrimidin-7-amines as ligands of the corticotropin-releasing factor type-1 (CRF1) receptor

A series of 3-(2,4-dichlorophenyl)-N-alkyl-N-fluoroalkyl-2,5-dimethylpyrazolo[1,5-a]pyrimidin-7-amines were synthesized and evaluated as potential positron emission tomography (PET) tracers for the corticotropin-releasing factor type-1 (CRF1) receptor. Compounds 27, 28, 29, and 30 all displayed high binding affinity (≤1.2 nM) to the CRF1 receptor when assessed by in vitro competition binding assays at 23 °C, whereas a decrease in affinity (≥10-fold) was observed with compound 26. The log P7.4 values of [18F]26-[18F]29 were in the range of ～2.2-2.8 and microPET evaluation of [18F]26-[18F]29 in an anesthetized male cynomolgus monkey demonstrated brain penetrance, but specific binding was not sufficient enough to differentiate regions of high CRF1 receptor density from regions of low CRF1 receptor density. Radioactivity uptake in the skull, and sphenoid bone and/or sphenoid sinus during studies with [18F]28, [18F]28-d8, and [18F]29 was attributed to a combination of [18F]fluoride generated by metabolic defluorination of the radiotracer and binding of intact radiotracer to CRF1 receptors expressed on mast cells in the bone marrow. Uptake of [18F]26 and [18F]27 in the skull and sphenoid region was rapid but then steadily washed out which suggests that this behavior was the result of binding to CRF1 receptors expressed on mast cells in the bone marrow with no contribution from [18F]fluoride.

Pyrazolo[1,5-a]pyrimidine CRF-1 receptor antagonists

A series of 3-phenylpyrazolo[1,5-a]pyrimidines was prepared and found to have affinity for the human CRF-1 receptor. The 3-dimensional structure of one of the most potent analogs in this series, 10d, was determined by X-ray crystallography and suggests the spatial requirements for potent CRF-1 receptor binding affinity in this series.