446859-33-2

Basic information

• Product Name: 2-(3-(6-METHYLPYRIDIN-2-YL)-1H-PYRAZOL-4-YL)-1,5-NAPHTHYRIDINE
• Synonyms: ALK5 INHIBITOR I;2-(3-(6-METHYLPYRIDIN-2-YL)-1H-PYRAZOL-4-YL)-1,5-NAPHTHYRIDINE;TGF-BETA RI KINASE INHIBITOR II;TRANSFORMING GROWTH FACTOR-BETA TYPE I RECEPTOR KINASE INHIBITOR I;2-(3-(6-Methylpyridine-2-yl)-1H-pyrazol-4-yl)-1,5-naphthyridine;SJN 2511;2-[3-(6-Methyl-2-pyridinyl)-1H-pyrazol-4-yl]-1,5-naphthyridine;RepSox
• CAS NO: 446859-33-2
• Molecular Formula: C17H13N5
• Molecular Weight: 287.31862
• Product Categories: Selective inhibitor of the TGF-β type I receptor ALK5.;Inhibitors;Smad;TGF-beta
• Mol File: 446859-33-2.mol
• Article Data: 2

Chemical Properties

• Melting Point: 195 °C
• Boiling Point: 501.911 °C at 760 mmHg
• Flash Point: 230.461 °C
• Appearance: /
• Density: 1.297 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.692
• Storage Temp.: Store at +4°C
• Solubility: DMSO: >20mg/mL
• PKA: 10.05±0.50(Predicted)
• Stability: Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 3 months.
• CAS DataBase Reference: 2-(3-(6-METHYLPYRIDIN-2-YL)-1H-PYRAZOL-4-YL)-1,5-NAPHTHYRIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(3-(6-METHYLPYRIDIN-2-YL)-1H-PYRAZOL-4-YL)-1,5-NAPHTHYRIDINE(446859-33-2)
• EPA Substance Registry System: 2-(3-(6-METHYLPYRIDIN-2-YL)-1H-PYRAZOL-4-YL)-1,5-NAPHTHYRIDINE(446859-33-2)

Safety Data

• Hazard Codes: T
• Statements: 25
• Safety Statements: 45
• RIDADR: UN 2811
• WGK Germany: 3
• Hazardous Substances Data: 446859-33-2(Hazardous Substances Data)

Usage

Description

2-(3-(6-METHYLPYRIDIN-2-YL)-1H-PYRAZOL-4-YL)-1,5-NAPHTHYRIDINE is a complex organic compound with a unique molecular structure. It is characterized by its pyrazol and naphthyridine moieties, which contribute to its potential applications in various fields. 2-(3-(6-METHYLPYRIDIN-2-YL)-1H-PYRAZOL-4-YL)-1,5-NAPHTHYRIDINE is known for its ability to interact with specific biological targets, making it a promising candidate for pharmaceutical and chemical research.

Uses

Used in Pharmaceutical Industry:
2-(3-(6-METHYLPYRIDIN-2-YL)-1H-PYRAZOL-4-YL)-1,5-NAPHTHYRIDINE is used as a potential therapeutic agent for the treatment of fibrosis and cancer. Its application is based on its ability to act as a selective ATP competitive inhibitor of transforming growth factor-β (TGFβ), which plays a crucial role in the development and progression of these diseases.
Used in Stem Cell Research:
In the field of stem cell research, 2-(3-(6-METHYLPYRIDIN-2-YL)-1H-PYRAZOL-4-YL)-1,5-NAPHTHYRIDINE is used as an inhibitor of autophosphorylation of the transforming growth factor β type I receptor kinase (ALK5). It has been shown to replace Sox2 in reprogramming adult cells into pluripotent stem cells by inducing the transcription of Nanog, a key factor in maintaining pluripotency. Additionally, it has been used in combination with other small molecules to convert astrocytes into neuronal cells, demonstrating its potential in cellular reprogramming and regenerative medicine.
Used in Chemical Research:
2-(3-(6-METHYLPYRIDIN-2-YL)-1H-PYRAZOL-4-YL)-1,5-NAPHTHYRIDINE is also utilized in chemical research as a starting material or intermediate for the synthesis of other complex organic compounds. Its unique structure and functional groups make it a valuable building block for the development of new molecules with potential applications in various industries, including pharmaceuticals, materials science, and agrochemistry.

Biochem/physiol Actions

RepSox Inhibits TGF-beta receptor signaling. Retroviral transduction of Sox2, Oct4, and Klf4 genes results in direct reprogramming of somatic cells into induced pluripotent stem cells (iPSCs).

References

1) Gellibert?et al. (2004),?Identification of 1,5-Naphthyridine Derivatives as a Novel Series of Potent and Selective TGF-β Type I Receptor Inhibitors; J. Med. Chem.?47?4494 2) Ichida?et al.?(2009),?A Small-molecule Inhibitor of TGF-β Signaling Replaces Sox2 in Reprogramming by Inducing Nanog; Cell Stem Cell?5?491 3) Cheng?et al.?(2015),?Direct Conversion of astrocytes into neuronal cells by a drug cocktail;?Cell Res.?25?1269 4) Cheng?et al.?(2014),?Generation of neural progenitor cells by chemical cocktails and hypoxia; Cell Res.?24?665

InChI:InChI=1/C17H13N5/c1-11-4-2-5-16(20-11)17-12(10-19-22-17)13-7-8-14-15(21-13)6-3-9-18-14/h2-10H,1H3,(H,19,22)

Upstream product

• 446297-56-9 1-(6-methylpyridin-2-yl)-2-(1,5-naphthyridin-2-yl)ethan-1-one 
• 7675-32-3 2-methyl-[1,5]naphthyridine 
• 80287-53-2 5-Amino-2-methylpyridine 
• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 

Relevant articles and documents

Synthesis and biological evaluation of 4(5)-(6-methylpyridin-2-yl)imidazoles and -pyrazoles as transforming growth factor-β type 1 receptor kinase inhibitors

A series of 4(5)-(6-methylpyridin-2-yl)imidazoles 16-19 and -pyrazoles 22-29, 33, and 34 have been synthesized and evaluated for their ALK5 inhibitory activity in an enzyme assay and in cell-based luciferase reporter assays. The 6-quinolinyl imidazole analogs 16 and 18 inhibited ALK5 phosphorylation with IC50 values of 0.026 and 0.034 μM, respectively. In a luciferase reporter assay using HaCaT cells transiently transfected with p3TP-luc reporter construct, 18 displayed 66% inhibition at 0.05 μM, while competitor compounds 2 and 3 showed 44% inhibition. The binding mode of 18 generated by flexible docking studies with ALK5:18 complex shows that it fits well into the active site cavity of ALK5 by forming broad and tight interactions.