1375262-94-4

Basic information

• Product Name: 5-(2-amino-4-methoxycarbonylphenyl)-2-butyl-1-(2-hydroxy-2-methylpropyl)-1H-imidazole-4-carbonitrile
• Synonyms: 5-(2-amino-4-methoxycarbonylphenyl)-2-butyl-1-(2-hydroxy-2-methylpropyl)-1H-imidazole-4-carbonitrile
• CAS NO: 1375262-94-4
• Molecular Weight: 370.451
• Mol File: 1375262-94-4.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 5-(2-amino-4-methoxycarbonylphenyl)-2-butyl-1-(2-hydroxy-2-methylpropyl)-1H-imidazole-4-carbonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(2-amino-4-methoxycarbonylphenyl)-2-butyl-1-(2-hydroxy-2-methylpropyl)-1H-imidazole-4-carbonitrile(1375262-94-4)
• EPA Substance Registry System: 5-(2-amino-4-methoxycarbonylphenyl)-2-butyl-1-(2-hydroxy-2-methylpropyl)-1H-imidazole-4-carbonitrile(1375262-94-4)

Safety Data

• Hazardous Substances Data: 1375262-94-4(Hazardous Substances Data)

Upstream product

• 1375262-96-6 2-butyl-1-(2-hydroxy-2-methylpropyl)-5-iodo-1H-imidazole-4-carbonitrile 
• 2363-16-8 methyl 4-bromo-3-nitrobenzoate 
• 6319-40-0 4-bromo-3-nitrobenzoic acid 
• 586-76-5 4-Bromobenzoic acid 
• 13820-09-2 trimethyl orthovalerate 
• 919-29-9 triethyl orthovalerate 
• 380430-55-7 (2-amino-4-(methoxycarbonyl)phenyl)boronic acid hydrochloride salt 
• 1375262-90-0 5-amino-2-butyl-1-(2-hydroxy-2-methylpropyl)-1H-imidazole-4-carbonitrile 

Downstream Products

• 1426395-64-3 2-butyl-7-methoxycarbonyl-4-{4-[(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)methyl]cyclohexanecarboxamido}-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinoline 

Relevant articles and documents

Design and Synthesis of N1-Modified Imidazoquinoline Agonists for Selective Activation of Toll-like Receptors 7 and 8

A series of N1-modified imidazoquinolines were synthesized and screened for Toll-like receptors (TLR) 7 and 8 activities to identify recognition elements that confer high affinity binding and selectivity. These receptors are key targets in the development of immunomodulatory agents that signal the NF-κB mediated transcription of pro-inflammatory chemokines and cytokines. Results are presented showing both TLR7/8 activations are highly correlated to N1-substitution, with TLR8 selectivity achieved through inclusion of an ethyl-, propyl-, or butylamino group at this position. While the structure-activity relationship analysis indicates TLR7 activity is less sensitive to N1-modification, extension of the aminoalkyl chain length to pentyl and p-methylbenzyl elicited high affinity TLR7 binding. Cytokine profiles are also reported that show the pure TLR8 agonist [4-amino-2-butyl-1-(2-aminoethyl)-7-methoxycarbonyl-1H-imidazo[4,5-c]quinoline] induces higher levels of IL-1β, IL-12, and IFNγ when compared with TLR7 selective or mixed TLR7/8 agonists. The results are consistent with previous work suggesting TLR8 agonists are Th1 polarizing and may help promote cell-mediated immunity.

IMMUNOMODULATORS AND IMMUNOMODULATOR CONJUGATES

The invention provides compounds of formula I: wherein R1-R3, Ra, and Rb have any of the values defined herein, and salts thereof. The compounds have immunomodulatory properties.