221243-77-2

Basic information

• Product Name: 4-AMINO-1-TERT-BUTYL-3-(1'-NAPHTHYLMETHYL)-4-CYANOPYRAZOLE
• Synonyms: 5-amino-1-(1,1-dimethylethyl)-3-(1-naphthalenylmethyl)- 1H-Pyrazole-4-carbonitrile 5-amino-1-(tert-butyl)-3-(1-naphthalenylmethyl)- 1H-Pyrazole-4-carbonitrile;5-Amino-1-tert-butyl-3-(1’-naphthylmethyl)-4-cyanopyrazole;5-aMino-1-(tert-butyl)-3-(naphthalen-1-ylMethyl)-1H-pyrazole-4-carbonitrile;5-Amino-1-tert-butyl-3-(1a€-naphthylmethyl)-4-cyanopyrazole
• CAS NO: 221243-77-2
• Molecular Formula: C19H20N4
• Molecular Weight: 304.39
• Product Categories: Tyrosine Kinase Inhibitors;Amines;Aromatics
• Mol File: 221243-77-2.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 516.4 °C at 760 mmHg
• Flash Point: 266.1 °C
• Appearance: /
• Density: 1.14 g/cm³
• Vapor Pressure: 8.99E-11mmHg at 25°C
• Refractive Index: 1.622
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• CAS DataBase Reference: 4-AMINO-1-TERT-BUTYL-3-(1'-NAPHTHYLMETHYL)-4-CYANOPYRAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-AMINO-1-TERT-BUTYL-3-(1'-NAPHTHYLMETHYL)-4-CYANOPYRAZOLE(221243-77-2)
• EPA Substance Registry System: 4-AMINO-1-TERT-BUTYL-3-(1'-NAPHTHYLMETHYL)-4-CYANOPYRAZOLE(221243-77-2)

Safety Data

• Hazardous Substances Data: 221243-77-2(Hazardous Substances Data)

Usage

Uses

A highly potent (IC50=1.5nM) and uniquely specific tyrosine kinase inhibitor of a rationally engineered v-Src tyrosine kinase

InChI:InChI=1/C19H20N4/c1-19(2,3)23-18(21)16(12-20)17(22-23)11-14-9-6-8-13-7-4-5-10-15(13)14/h4-10H,11,21H2,1-3H3

Upstream product

• 86-87-3 naphth-1-yl acetic acid 
• 32064-67-8 tert-butylhydrazine 
• 221243-13-6 2-(1-methoxy-2-naphthalen-1-ylethylidene)malononitrile 
• 5121-00-6 naphthalen-1-yl-acetyl chloride 
• 7400-27-3 tertbutylhydrazine hydrochloride 

Downstream Products

• 221244-14-0 1-tert-butyl-3-(naphthalen-1-ylmethyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine 

Relevant articles and documents

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.

Generation of monospecific nanomolar tyrosine kinase inhibitors via a chemical genetic approach

Selective protein kinase inhibitors are highly sought after as tools for studying cellular signal transduction cascades, yet few have been discovered due to the highly conserved fold of kinase catalytic domains. Through a combination of small molecule syn