57806-32-3

Basic information

• Product Name: 3-Amino-4-(benzylamino)pyridine
• Synonyms: 3-Amino-4-(benzylamino)pyridine
• CAS NO: 57806-32-3
• Molecular Formula: C₁₂H₁₃N₃
• Molecular Weight: 199.25
• Product Categories: pharmacetical
• Mol File: 57806-32-3.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-Amino-4-(benzylamino)pyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Amino-4-(benzylamino)pyridine(57806-32-3)
• EPA Substance Registry System: 3-Amino-4-(benzylamino)pyridine(57806-32-3)

Safety Data

• Hazardous Substances Data: 57806-32-3(Hazardous Substances Data)

Upstream product

• 100306-70-5 4-(benzylamino)-3-nitropyridine 
• 239137-39-4 3-amino-4-bromopyridine 
• 100-46-9 benzylamine 

Downstream Products

• 124897-37-6 1-Benzyl-2-pyridin-2-yl-1H-imidazo[4,5-c]pyridine 
• 124897-35-4 1-benzyl-2-(5-ethyl-2-pyridiyl)-1H-imidazo<4,5-c>pyridine 
• 34477-54-8 1-Benzyl-1,3-dihydro-imidazo[4,5-c]pyridine-2-thione 
• 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 
• 34477-52-6 1-benzyl-1H-imidazo[4,5-c]pyridine 
• 108564-91-6 1-benzyl-1H-[1,2,3]triazolo[4,5-c]pyridine 

Relevant articles and documents

Rapid construction of imidazopyridines from ortho-haloaminopyridines

A practical strategy for the preparation of imidazopyridine derivatives from ortho-haloaminopyridines utilizing a two-step C-N coupling/cyclization reaction sequence has been developed. This procedure provides rapid and efficient access to many medicinally interesting imidazopyridine compounds and related imidazopyrazine/purine heterocycles.

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.