100306-70-5

Basic information

• Product Name: 4-BENZYLAMINO-3-NITROPYRIDINE
• Synonyms: 4-BENZYLAMINO-3-NITROPYRIDINE
• CAS NO: 100306-70-5
• Molecular Formula: C₁₂H₁₁N₃O₂
• Molecular Weight: 229.23
• Product Categories: Pyridine series;Pyridine
• Mol File: 100306-70-5.mol

Chemical Properties

• Boiling Point: 397.847 °C at 760 mmHg
• Flash Point: 194.411 °C
• Appearance: /
• Density: 1.312 g/cm³
• Vapor Pressure: 1.54E-06mmHg at 25°C
• Refractive Index: 1.666
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 4-BENZYLAMINO-3-NITROPYRIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-BENZYLAMINO-3-NITROPYRIDINE(100306-70-5)
• EPA Substance Registry System: 4-BENZYLAMINO-3-NITROPYRIDINE(100306-70-5)

Safety Data

• Hazardous Substances Data: 100306-70-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-BENZYLAMINO-3-NITROPYRIDINE is used as a building block in organic synthesis for the development of various pharmaceuticals. Its unique structure allows for the creation of complex organic molecules, contributing to the advancement of drug discovery and design.
Used in Fine Chemicals Production:
In the fine chemicals industry, 4-BENZYLAMINO-3-NITROPYRIDINE is utilized as an intermediate for synthesizing specialty chemicals with specific applications, such as agrochemicals, dyes, and other high-value compounds.
Used in Chemical Research:
4-BENZYLAMINO-3-NITROPYRIDINE serves as a reagent in chemical research, facilitating experiments and studies aimed at understanding its biological and pharmacological properties, as well as exploring its potential applications in various chemical processes.
Used in Commercial Applications:
4-BENZYLAMINO-3-NITROPYRIDINE is commercially available for a variety of research and industrial applications, providing a foundation for innovation in chemical synthesis and the development of new products across different sectors.

InChI:InChI=1/C12H11N3O2/c16-15(17)12-9-13-7-6-11(12)14-8-10-4-2-1-3-5-10/h1-7,9H,8H2,(H,13,14)

Upstream product

• 13091-23-1 4-chloro-3-nitropyridine 
• 100-46-9 benzylamine 
• 7732-18-5 water 
• 31872-62-5 4-methoxy-3-nitro-pyridine 
• 5435-54-1 4-hydroxy-3-nitropyridine 
• 626-64-2 pyridin-4-ol 
• 94602-04-7 4-ethoxy-3-nitropyridine hydrochloride 

Downstream Products

• 57806-32-3 N⁴-benzylpyridine-3,4-diamine 
• 54-96-6 3,4-diaminopyridine 
• 124897-39-8 1-benzyl-2-(4-pyridyl)-1H-imidazo<4,5-c>pyridine 
• 124897-35-4 1-benzyl-2-(5-ethyl-2-pyridiyl)-1H-imidazo<4,5-c>pyridine 
• 133563-50-5 N⁴-benzyl-2-chloropyridine-3,4-diamine 
• 1026226-70-9 1-Benzyl-4-chloro-1H-[1,2,3]triazolo[4,5-c]pyridine 
• 108564-91-6 1-benzyl-1H-[1,2,3]triazolo[4,5-c]pyridine 
• 120537-43-1 1-benzyl-4-chloro-1H-imidazo<4,5-c>pyridine 
• 1457966-65-2 1-benzyl-2-butyl-1H-imidazo[4,5-c]pyridine 
• 1457966-66-3 1-benzyl-2-butyl-1H-imidazo[4,5-c]pyridine 5-oxide 
• 1457966-67-4 1-benzyl-2-butyl-1H-imidazo[4,5-c]pyridin-4-amine 
• 1457966-75-4 N-(1-benzyl-2-butyl-1H-imidazo[4,5-c]pyridin-4-yl)acetamide 
• 1457966-76-5 N-(1-benzyl-2-butyl-1H-imidazo[4,5-c]pyridin-4-yl)butyramide 

Relevant articles and documents

TOLL-LIKE RECEPTOR AGONISTS

Compounds described herein can be used for therapeutic purposes. The compounds can be TLR agonists, such as TLR7 or TLR8 agonists. The compounds can be included in pharmaceutical compositions and used for therapies were being a TLR agonist is useful. The pharmaceutical compositions can include any ingredients, such as carries, diluents, excipients, fillers or the like that are common in pharmaceutical compositions. The compounds can be those illustrated or described herein as well as derivatives thereof, prodrugs thereof, salts thereof, or stereoisomers thereof, or having any chirality at any chiral center, or tautomer, polymorph, solvate, or combinations thereof. As such, the compounds can be used as adjuvants in vaccines, as well as for other therapeutic purposes described herein.

Structure-activity relationships in Toll-like receptor 7 agonistic 1H-imidazo[4,5-c]pyridines

Engagement of TLR7 in plasmacytoid dendritic cells leads to the induction of IFN-α/β which plays essential functions in the control of adaptive immunity. We had previously examined structure-activity relationships (SAR) in TLR7/8-agonistic imidazoquinolines with a focus on substituents at the N 1, C2, N3 and N4 positions, and we now report SAR on 1H-imidazo[4,5-c]pyridines. 1-Benzyl-2-butyl-1H-imidazo[4,5-c] pyridin-4-amine was found to be a pure TLR7-agonist with negligible activity on TLR8. Increase in potency was observed in N6-substituted analogues, especially in those compounds with electron-rich substituents. Direct aryl-aryl connections at C6 abrogated activity, but TLR7 agonism was reinstated in 6-benzyl and 6-phenethyl analogues. Consistent with the pure TLR7-agonistic behavior, prominent IFN-α induction in human PBMCs was observed with minimal proinflammatory cytokine induction. A benzologue of imidazoquinoline was also synthesized which showed substantial improvements in potency over the parent imidazopyridine. Distinct differences in N6-substituted analogues were observed with respect to IFN-α induction in human PBMCs on the one hand, and CD69 upregulation in lymphocytic subsets, on the other.

Practical amination of nitropyridones by silylation

A practical method for coupling nitropyridones (1) with primary amines by treatment with hexamethyldisilazane has been developed, avoiding the use of hazardous reagents such as POCl3. The activation of the pyridone by a nitro group is necessary for efficient coupling, leading to aminonitropyridines (3) in good yields. Regioisomers other than 3-nitro-4-pyridone (1) were found to be substantially less reactive but would undergo coupling with primary amines.

Structure-guided design of substituted aza-benzimidazoles as potent hypoxia inducible factor-1α prolyl hydroxylase-2 inhibitors

We report the structure-based design and synthesis of a novel series of aza-benzimidazoles as PHD2 inhibitors. These efforts resulted in compound 22, which displayed highly potent inhibition of PHD2 function in vitro.

IMIDAZOPYRIDINES AS MUSCARINIC AGENTS

The compound of the formula: STR1 where R 1 is H, alkyl, perhaloalkyl, arylalkyl, alkenyl or alkynyl; R 2 is H when R. sub.4 is other than H, and, when R 4 is H, R 2 is STR2 in which R 5 is hydrogen or alkyl; R 3 is hydrogen or halogen; R. sub.4 is H or STR3 X, Y and Z are, independently, nitrogen or carbon, at least one of X, Y or Z being nitrogen; n is 1 or 2; n 1 is 0, 1, 2, 3, 4, or 5; or a pharmaceutically acceptable salt thereof are centrally active muscarinic agents.

1-(Fluorobenzyl)-4-amino-1H-1,2,3-triazolo[4,5-c]pyridines: Synthesis and anticonvulsant activity

A series of (fluorobenzyl)triazolo[4,5-c]pyridines was synthesized and tested for activity against maximal electroshock-induced seizures in rodents. The most promising compound, 14 (BW 534U87), which is a carbon-nitrogen isoster of a purine anticonvulsant, has a profile in rodents that suggests 14 will be free of emesis and useful in the treatment of seizure disorders for which phenytoin is presently indicated.

Pharmaceutically active triazolopyridine compounds

This invention describes the preparation and use of anticonvulsant agents. In particular, triazolopyridine compounds are described which have utility in the treatment of epilepsy in mammals.