112668-45-8

Usage

InChI:InChI=1/C14H16N4O/c1-14(2,19)7-18-8-16-11-12(18)9-5-3-4-6-10(9)17-13(11)15/h3-6,8,19H,7H2,1-2H3,(H2,15,17)

Upstream product

• 1375262-91-1 5-(2-aminophenyl)-1-(2-hydroxy-2-methylpropyl)-1H-imidazole-4-carbonitrile 
• 1375262-89-7 5-amino-1-(2-hydroxy-2-methylpropyl)-1H-imidazole-4-carbonitrile 
• 200198-35-2 α,α-Dimethyl-6H-imidazo [4,5-c]tetrazolo[1,5-a]quinoline-6-ethanol 
• 95-50-1 1,2-dichloro-benzene 
• 132521-66-5 2,4-dichloro-3-nitroquinoline 
• 15151-57-2 4-hydroxy-3-nitro-1,2-dihydroquinolin-2-one 
• 133860-77-2 1-[(2-chloro-3-nitro-4-quinolinyl)amino]-2-methyl-2-propanol 
• 133860-78-3 1-[(3-amino-2-chloro-4-quinolinyl)amino]-2-methyl-2-propanol 
• 129655-65-8 4-chloro-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]-quinoline 

Relevant academic research and scientific papers

Discovery of imidazoquinolines with toll-like receptor 7/8 independent cytokine induction

Toll-like receptors (TLRs) are key targets in the design of immunomodulating agents for use as vaccine adjuvants and anticancer treatments. The imidazoquinolines, imiquimod and resiquimod, have been shown to activate TLR-7 and -8, which in turn induce cytokine production as part of the innate immune response. Herein, we report the synthesis and discovery of a C7-methoxycarbonyl derivative of imiquimod that stimulates cytokine production but is devoid of TLR-7/8 activity. Data are presented that shows that this analogue not only induces IL-12p40 and TNF production, similar to that of imiquimod and resiquimod, but greatly enhances the production of IL-1β, a key cytokine involved in the activation of CD4 T cells. It is further demonstrated that TLR-7/8 activation can be recovered by the addition of a C2-alkyl substituent to this newly discovered analogue. The results support the existence of an alternative mechanism of action by which imidazoquinolines can stimulate cytokine production.

Synthesis and structure - Activity-relationships of 1H-imidazo[4,5-c] quinolines that induce interferon production

1H-Imidazo-[4,5-c]quinolines were prepared while investigating novel nucleoside analogues as potential antiviral agents. While these compounds showed no direct antiviral activity when tested in a number of cell culture systems, some demonstrated potent inhibition of virus lesion development in an intravaginal guinea pig herpes simplex virus-2 assay. We have determined that the in vivo antiviral activity can be attributed to the ability of these molecules to induce the production of cytokines, especially interferon (IFN), in this model. Subsequently, we found that the compounds also induce in vitro production of IFN in human peripheral blood mononuclear cells (hPBMCs). The in vitro results reported herein and the in vivo results reported previously led to the discovery of imiquimod, 26, which was developed as a topical agent and has been approved for the treatment of genital warts, actinic keratosis, and superficial basal cell carcinoma.

Use of immidazoquinolinamines as adjuvants in dna vaccination

The present invention relates to the use of a 1H-imidazo[4,5-c]-4-amine derivative as an adjuvant for use with nucleic acid vaccination.

Process for reparing imidazoquinolinamines

A process for preparing 1H-imidazo?4,5-c!quinolin-4-amines is disclosed. The process involves reacting a 6H-imidazo?4,5-c!tetrazolo?1,5-a!quinoline with triphenylphosphine and hydrolyzing the product thereof.

1H-IMIDAZO[4,5-C]QUINOLIN-4-AMINES AND ANTIVIRAL USE

1H-Imidazo[4,5-c]quinolin-4-amines which are antivirals. Pharmacological methods of using such compounds and pharmaceutical compositions containing such compounds are also described