778611-16-8

Basic information

• Product Name: 3-TERT-BUTYL-1-(4-FLUOROPHENYL)-1H-PYRAZOL-5-AMINE
• Synonyms: BUTTPARK 74\09-01;3-TERT-BUTYL-1-(4-FLUOROPHENYL)-1H-PYRAZOL-5-AMINE;5-TERT-BUTYL-2-(4-FLUORO-PHENYL)-2H-PYRAZOL-3-YLAMINE;5-tert-butyl-2-(4-fluorophenyl)pyrazol-3-amine
• CAS NO: 778611-16-8
• Molecular Formula: C₁₃H₁₆FN₃
• Molecular Weight: 233.28
• Product Categories: C12 to C37;Halogenated Heterocycles;Building Blocks;Chemical Synthesis;Heterocyclic Building Blocks;New Products for Chemical Synthesis;Pyrazoles
• Mol File: 778611-16-8.mol
• Article Data: 11

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C(protect from light)
• CAS DataBase Reference: 3-TERT-BUTYL-1-(4-FLUOROPHENYL)-1H-PYRAZOL-5-AMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-TERT-BUTYL-1-(4-FLUOROPHENYL)-1H-PYRAZOL-5-AMINE(778611-16-8)
• EPA Substance Registry System: 3-TERT-BUTYL-1-(4-FLUOROPHENYL)-1H-PYRAZOL-5-AMINE(778611-16-8)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• WGK Germany: 3
• Hazardous Substances Data: 778611-16-8(Hazardous Substances Data)

Usage

General Description

3-TERT-BUTYL-1-(4-FLUOROPHENYL)-1H-PYRAZOL-5-AMINE, also known as tert-butyl-(4-fluorophenyl)pyrazol-3-ylamine, is a chemical compound with the molecular formula C13H16FN3. It is a pyrazole derivative with a tert-butyl substituent at the 3-position and a 4-fluorophenyl group at the 1-position. 3-TERT-BUTYL-1-(4-FLUOROPHENYL)-1H-PYRAZOL-5-AMINE is commonly used in the pharmaceutical industry as a building block in the synthesis of various biologically active molecules. It has been reported to have potential pharmacological activities, including as an inhibitor of kinase enzymes. Its structure and properties make it a valuable intermediate in the development of new drugs and agrochemicals.

Upstream product

• 371-14-2 4-fluorophenylhydrazine 
• 59997-51-2 trimethylacetylacetonitrile 
• 823-85-8 4-fluorophenyhydrazine hydrochloride 

Downstream Products

• 950643-44-4 6-(6-chloro-pyrimidin-4-yloxy)-naphthalene-1-carboxylic acid [5-tert-butyl-2-(4-fluoro-phenyl)-2H-pyrazol-3-yl]-amide 
• 871557-51-6 phenyl (3-(tert-butyl)-1-(4-fluorophenyl)-1H-pyrazol-5-yl)carbamate 
• 952105-77-0 1-[5-tert-butyl-2-(4-fluoro-phenyl)-2H-pyrazol-3-yl]-3-[4-((Z)-1-cyano-2-dimethylamino-vinyl)-phenyl]urea 
• 1071964-47-0 1-(3-tert-butyl-1-(4-fluorophenyl)-1H-pyrazol-5-yl)-3-(5-(2-morpholinoethoxy)-2H-chromen-8-yl)urea 

Relevant articles and documents

Selective targeting of the αC and DFG-out pocket in p38 MAPK

The p38 MAPK cascade is a key signaling pathway linked to a multitude of physiological functions and of central importance in inflammatory and autoimmune diseases. Although studied extensively, little is known about how conformation-specific inhibitors alter signaling outcomes. Here, we have explored the highly dynamic back pocket of p38 MAPK with allosteric urea fragments. However, screening against known off-targets showed that these fragments maintained the selectivity issues of their parent compound BIRB-796, while combination with the hinge-binding motif of VPC-00628 greatly enhanced inhibitor selectivity. Further efforts focused therefore on the exploration of the αC-out pocket of p38 MAPK, yielding compound 137 as a highly selective type-II inhibitor. Even though 137 is structurally related to a recent p38 type-II chemical probe, SR-318, the data presented here provide valuable insights into back-pocket interactions that are not addressed in SR-318 and it provides an alternative chemical tool with good cellular activity targeting also the p38 back pocket.

Biophysical investigation and conformational analysis of p38α kinase inhibitor doramapimod and its analogues

Doramapimod (BIRB 796) is a potent inhibitor of p38α mitogen-activated protein kinase. It contains an aryl-pyrazole scaffold as a pharmacophore critical for binding. The aryl-pyrazole scaffold is not planar and adopts an out-of-plane conformation, which is described by the torsion angle θ. In this letter, we report the chemical synthesis and biophysical characterization of different analogues of doramapimod (3-12) exhibiting distinctly different aryl-pyrazole torsion angle θ values. The torsion angle θ values of the synthesized analogues (3-6) were determined by crystal structural analysis and the binding affinities to p38α kinase investigated by microscale thermophoresis. Our results unveil a clear correlation between kinase binding and the torsion angle θ of tested doramapimod analogues, highlighting the importance of inhibitor conformation for protein binding.

Synthesis and Biological Evaluation of Chromenylurea and Chromanylurea Derivatives as Anti-TNF-a agents that Target the p38 MAPK Pathway

A series of 1-aryl-3-(2H-chromen-5-yl)urea and 1-aryl-3-(chroman-5-yl)urea derivatives were designed, synthesized and evaluated for their inhibitory activities towards TNF-a production in lipopolysaccharide-stimulated THP-1 cells. The most active compound, 40g, inhibited TNF-a release with an IC50 value of 0.033 μM, which is equipotent to that of BIRB796 (IC50 = 0.032 μM).