21626-43-7

Basic information

• Product Name: 2-AMino-6-(benzylaMino)-3-nitropyridine
• Synonyms: 2-AMino-6-(benzylaMino)-3-nitropyridine
• CAS NO: 21626-43-7
• Molecular Formula: C₁₂H₁₂N₄O₂
• Molecular Weight: 244.24928
• Product Categories: Amines, Heterocycles, Metabolites & Impurities, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 21626-43-7.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 460.4±45.0 °C(Predicted)
• Appearance: /
• Density: 1.380±0.06 g/cm3(Predicted)
• PKA: 1.71±0.50(Predicted)
• CAS DataBase Reference: 2-AMino-6-(benzylaMino)-3-nitropyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-AMino-6-(benzylaMino)-3-nitropyridine(21626-43-7)
• EPA Substance Registry System: 2-AMino-6-(benzylaMino)-3-nitropyridine(21626-43-7)

Safety Data

• Hazardous Substances Data: 21626-43-7(Hazardous Substances Data)

Usage

Uses

2-Amino-6-(benzylamino)-3-nitropyridine is used in the synthesis of triaminopyridines, used as anticonvulsants. An impurity in the synthesis of Flupirtine (F598510), an analgesic. Substituted pyridine with central analgesic properties.

Upstream product

• 16013-85-7 2,6-dicholoro-3-nitropyridine 
• 27048-04-0 2-amino-6-chloro-3-nitropyridine 
• 100-46-9 benzylamine 

Downstream Products

• 21630-56-8 ethyl <2-amino-6-(benzylamino)pyridin-3-yl>carbamate hydrochloride 
• 21630-55-7 N⁶-benzyl-pyridine-2,3,6-triaine 

Relevant articles and documents

Design of a novel and selective IRAK4 inhibitor using topological water network analysis and molecular modeling approaches

Protein kinases are deeply involved in immune-related diseases and various cancers. They are a potential target for structure-based drug discovery, since the general structure and characteristics of kinase domains are relatively well-known. However, the ATP binding sites in protein kinases, which serve as target sites, are highly conserved, and thus it is difficult to develop selective kinase inhibitors. To resolve this problem, we performed molecular dynamics simulations on 26 kinases in the aqueous solution, and analyzed topological water networks (TWNs) in their ATP binding sites. Repositioning of a known kinase inhibitor in the ATP binding sites of kinases that exhibited a TWN similar to interleukin-1 receptor-associated kinase 4 (IRAK4) allowed us to identify a hit molecule. Another hit molecule was obtained from a commercial chemical library using pharmacophore-based virtual screening and molecular docking approaches. Pharmacophoric features of the hit molecules were hybridized to design a novel compound that inhibited IRAK4 at low nanomolar levels in the in vitro assay.

Synthesis and quantitative structure-activity relationships of anticonvulsant 2,3,6-triaminopyridines

The synthesis of 2,3,6-triaminopyridine derivatives, representing a unique chemical structure for anticonvulsants, is described. The synthetic program was performed (a) to identify more potent analogs, (b) to determine structural properties controlling potency as well as neurotoxicity, and (c) to reduce the requirements for animal testing. As a result, besides other structural properties, the overall molecular lipophilicity (log k', octanol- coated column) explained changes in anticonvulsant potency and neurotoxicity. Mimicking the interaction of the amphiphilic triaminopyridines with biological membranes, NMR experiments in the presence of lecithin vesicles were conducted in order to measure the phospholipid-binding parameter log Δ(1/T2). Replacement of log k' with log Δ(1/T2) in the correlation analysis afforded a more significant equation describing the anticonvulsant activity of 21 derivatives.