1457967-11-1

Basic information

• Product Name: 1-benzyl-2-butyl-4-chloro-1H-imidazo[4,5-c]pyridine
• Synonyms: 1-benzyl-2-butyl-4-chloro-1H-imidazo[4,5-c]pyridine
• CAS NO: 1457967-11-1
• Molecular Weight: 299.803
• Mol File: 1457967-11-1.mol

Chemical Properties

• CAS DataBase Reference: 1-benzyl-2-butyl-4-chloro-1H-imidazo[4,5-c]pyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-benzyl-2-butyl-4-chloro-1H-imidazo[4,5-c]pyridine(1457967-11-1)
• EPA Substance Registry System: 1-benzyl-2-butyl-4-chloro-1H-imidazo[4,5-c]pyridine(1457967-11-1)

Safety Data

• Hazardous Substances Data: 1457967-11-1(Hazardous Substances Data)

Upstream product

• 14432-12-3 4-Amino-2-chloropyridine 
• 133563-50-5 N⁴-benzyl-2-chloropyridine-3,4-diamine 
• 100-39-0 benzyl bromide 
• 638-29-9 n-valeryl chloride 

Downstream Products

• 1457966-78-7 N,1-dibenzyl-2-butyl-1H-imidazo[4,5-c]pyridin-4-amine 
• 1457966-77-6 1-benzyl-N,2-dibutyl-1H-imidazo[4,5-c]pyridin-4-amine 
• 1457967-13-3 1-benzyl-4-butoxy-2-butyl-1H-imidazo[4,5-c]pyridine 

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.