864292-49-9

Basic information

• Product Name: 1-tert-butyl-4,6-dichloro-1H-pyrazolo[3,4-d]pyrimidine
• Synonyms: 1-tert-butyl-4,6-dichloro-1H-pyrazolo[3,4-d]pyrimidine
• CAS NO: 864292-49-9
• Molecular Formula: C9H10Cl2N4
• Molecular Weight: 245.11
• Mol File: 864292-49-9.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 1-tert-butyl-4,6-dichloro-1H-pyrazolo[3,4-d]pyrimidine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-tert-butyl-4,6-dichloro-1H-pyrazolo[3,4-d]pyrimidine(864292-49-9)
• EPA Substance Registry System: 1-tert-butyl-4,6-dichloro-1H-pyrazolo[3,4-d]pyrimidine(864292-49-9)

Safety Data

• Hazardous Substances Data: 864292-49-9(Hazardous Substances Data)

Usage

Type of compound

pyrazolopyrimidine derivative

Uses

Building block for the synthesis of biologically active compounds, potential anticancer agent

Known for

Inhibitory effects on enzymes and proteins involved in cancer cell growth and proliferation

Substitutions

tert-butyl and dichloro

Benefits

Stability and reactivity in chemical reactions, valuable intermediate in the production of pharmaceutical drugs and agrochemicals

Potential applications

Material science and catalysis.

Upstream product

• 32064-67-8 tert-butylhydrazine 
• 50270-27-4 2,4,6-trichloropyrimidine-5-carbaldehyde 
• 7400-27-3 tertbutylhydrazine hydrochloride 

Downstream Products

• 1361960-64-6 1-tert-butyl-6-(4-fluorophenylsulfonyl)-N-(5-methyl-1H-pyrazol-3-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine 

Relevant articles and documents

PYRIMIDINE AMIDE COMPOUNDS AND USE THEREOF

Disclosed are compounds of formula (I) below or a stereoisomer, a tautomer, or a pharmaceutically acceptable salt thereof: (I), in which each of variables each of variables R, R1, R2, X1, X2, X3 and n is defined herein. Also disclosed is a method for treating a cancer with a compound of formula (I) or a salt thereof and a pharmaceutical composition containing same.

Discovery of a potent protein kinase D inhibitor: insights in the binding mode of pyrazolo[3,4-d]pyrimidine analogues

In this study, we set out to rationally optimize PKD inhibitors based on the pyrazolo[3,4-d]pyrimidine scaffold. The lead compound for this study was 1-NM-PP1, which was previously found by us and others to inhibit PKD. In our screening we identified one compound (3-IN-PP1) displaying a 10-fold increase in potency over 1-NM-PP1, opening new possibilities for specific protein kinase inhibitors for kinases that show sensitivity towards pyrazolo[3,4-d]pyrimidine derived compounds. Interestingly the observed SAR was not in complete agreement with the commonly observed binding mode where the pyrazolo[3,4-d]pyrimidine compounds are bound in a similar fashion as PKD's natural ligand ATP. Therefore we suggest an alternate binding mode where the compounds are flipped 180 degrees. This possible alternate binding mode for pyrazolo[3,4-d]pyrimidine based compounds could pave the way for a new class of specific protein kinase inhibitors for kinases sensitive towards pyrazolo[3,4-d]pyrmidines.

AZOLOPYRIDINE AND AZOLOPYRIMIDINE COMPOUNDS AND METHODS OF USE THEREOF

Provided herein are azolopyridine and azolopyrimidine compounds for treatment of JAK kinase mediated diseases, including JAK2 kinase-, JAK3 kinase- or TYK2 kinase-mediated diseases. Also provided are pharmaceutical compositions comprising the compounds and methods of using the compounds and compositions.