1006333-08-9

Basic information

• Product Name: 1-(2,2-difluoroethyl)-1H-pyrazol-4-ylamine
• Synonyms: 1-(2,2-difluoroethyl)-1H-pyrazol-4-ylamine;1-(2,2-DIFLUOROETHYL)-1H-PYRAZOL-4-AMINE;1H-Pyrazol-4-amine, 1-(2,2-difluoroethyl)-
• CAS NO: 1006333-08-9
• Molecular Formula: C₅H₇F₂N₃
• Molecular Weight: 147.13
• Mol File: 1006333-08-9.mol
• Article Data: 11

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-(2,2-difluoroethyl)-1H-pyrazol-4-ylamine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2,2-difluoroethyl)-1H-pyrazol-4-ylamine(1006333-08-9)
• EPA Substance Registry System: 1-(2,2-difluoroethyl)-1H-pyrazol-4-ylamine(1006333-08-9)

Safety Data

• Hazardous Substances Data: 1006333-08-9(Hazardous Substances Data)

Usage

Description

1-(2,2-difluoroethyl)-1H-pyrazol-4-ylamine is a chemical compound with the molecular formula C7H7F2N3. It is a derivative of pyrazole, a five-membered heterocyclic compound containing nitrogen. The presence of a difluoroethyl group attached to the first position and an amine group at the fourth position gives this compound unique properties and potential applications in various fields.

Uses

Used in Pharmaceutical Industry:
1-(2,2-difluoroethyl)-1H-pyrazol-4-ylamine is used as a reagent for the development of pyrimidine derivatives. These derivatives have potential applications as inhibitors of JAK3, a protein tyrosine kinase involved in various cellular processes, including immune response and cell growth. By inhibiting JAK3, these pyrimidine derivatives can potentially be used in the treatment of autoimmune diseases, inflammatory disorders, and certain types of cancer.
The compound's unique structure, with its difluoroethyl and amine functional groups, allows it to be a versatile building block in the synthesis of various bioactive molecules. Its use in the pharmaceutical industry is primarily due to its ability to contribute to the development of novel therapeutic agents targeting JAK3, which can have significant implications in the treatment of various diseases.

Upstream product

• 2075-46-9 4-nitro-1H-pyrazole 
• 598-39-0 1,1-difluoro-2-iodoethane 
• 1006442-51-8 1-(2,2-difluoroethyl)-4-nitro-1H-pyrazole 
• 163035-65-2 methanesulfonic acid 2,2-difluoroethyl ester 

Downstream Products

• 1346161-55-4 N-(1-(2,2-difluoroethyl)-1H-pyrazol-4-yl)-1-((1-(methylsulfonyl)piperidin-3-yl)methyl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine 
• 1346162-22-8 N-(1-(2,2-difluoroethyl)-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine 

Relevant articles and documents

A practical, two-step synthesis of 1-alkyl-4-aminopyrazoles

A novel synthesis of N1 alkyl-substituted pyrazoles with a free amino group at the C4 position is described. Commercially available 4-nitropyrazole was found to readily undergo Mitsunobu reactions with primary and secondary alcohols. Subsequent reduction of the nitro group via hydrogenation affords 1-alkyl-4-aminopyrazoles, which are valuable intermediates in the synthesis of pharmaceutically active compounds.

Discovery of 7H-pyrrolo[2,3-d]pyridine derivatives as potent FAK inhibitors: Design, synthesis, biological evaluation and molecular docking study

Focal adhesion kinase (FAK) is an intracellular non-receptor tyrosine kinase responsible for development of various tumor types. Aiming to explore new potent inhibitors, two series of 2,4-disubstituted-7H-pyrrolo[2,3-d]pyrimidine derivatives were designed and synthesized on the base of structure-based design strategy. Biological evaluation indicated that most of these new compounds could potently inhibit FAK kinase, leading to the promising inhibitors against the proliferation of U-87MG, A-549, and MDA-MB-231 cancer cell lines. Among them, the optimized compound 18h potently inhibited the enzyme (IC50 = 19.1 nM) and displayed stronger potency than TAE-226 in U-87MG, A-549 and MDA-MB-231 cells, with IC50 values of 0.35, 0.24, and 0.34 μM, respectively. Compound 18h is a multi-target kinase inhibitor. Furthermore, compound 18h also exhibited relatively less cytotoxicity (IC50 = 3.72 μM) toward a normal human cell line, HK2. According to the flow cytometry and wound healing assay results, compound 18h effectively induced apoptosis and G0/G1 phase arrest of MDA-MB-231 cells and suppressed the migration of U-87MG, A-549 and MDA-MB-231 cells. The docking study of compound 18h was performed to elucidate its possible binding modes and to provide a structural basis for the further structural guidance design of FAK inhibitors. Collectively, these data support the further development of compound 18h as a lead compound for FAK-targeted anticancer drug discovery.

Design, synthesis and biological evaluation of novel 7H-pyrrolo[2,3-d]pyrimidine derivatives as potential FAK inhibitors and anticancer agents

A series of 7H-pyrrolo[2,3-d]pyrimidine derivatives possessing a dimethylphosphine oxide moiety were designed, synthesized and evaluated as novel Focal adhesion kinase (FAK) inhibitors. Most compounds potently suppressed the enzymatic activities of FAK, with IC50 values in the 10?8–10?9 M range, and potently inhibited the proliferation of breast (MDA-MB-231) and lung (A549) cancer cell lines. The representative compound 25b exhibited potent enzyme inhibition (IC50 = 5.4 nM) and good selectivity when tested on a panel of 26 kinases. 25b exhibited antiproliferative activity against A549 cells (IC50 = 3.2 μM) and relatively less cytotoxicity to a normal human cell line HK2. Compound 25b also induced apoptosis and suppressed the migration of A549 cells in a concentration-dependent manner. Further profiling of compound 25b revealed it had good metabolic stability in mouse, rat and human liver microsomes in vitro and showed weak inhibitory activity against various subtypes of human cytochrome P450. The docking study of compound 25b was performed to elucidate its possible binding modes and to provide a structural basis for further structure-guided design of FAK inhibitors.