99010-24-9

Basic information

• Product Name: 1-(2-METHYLPROPYL)-1H-IMIDAZO[4,5-C]QUINOLINE
• Synonyms: 1H-IMIDAZO[4,5-C]QUINOLINE, 1-(2-METHYLPROPYL)-;1-ISOBUTYL-1H-IMIDAZO[4,5-C]QUINOLINE;1-(2-METHYLPROPYL)-1H-IMIDAZO[4,5-C]QUINOLINE;Imiquimod Related Compound A (25 mg) (1-Isobutyl-1H-imidazo[4,5-c]quinoline);IMiquiMod Related CoMpound A;DesaMino IMiquiMod
• CAS NO: 99010-24-9
• Molecular Formula: C₁₄H₁₅N₃
• Molecular Weight: 225.29
• Mol File: 99010-24-9.mol
• Article Data: 8

Chemical Properties

• Melting Point: 92-95℃
• Boiling Point: 402.6°C at 760 mmHg
• Flash Point: 197.3°C
• Appearance: /
• Density: 1.17g/cm³
• Vapor Pressure: 1.08E-06mmHg at 25°C
• Refractive Index: 1.643
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 5.34±0.30(Predicted)
• CAS DataBase Reference: 1-(2-METHYLPROPYL)-1H-IMIDAZO[4,5-C]QUINOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2-METHYLPROPYL)-1H-IMIDAZO[4,5-C]QUINOLINE(99010-24-9)
• EPA Substance Registry System: 1-(2-METHYLPROPYL)-1H-IMIDAZO[4,5-C]QUINOLINE(99010-24-9)

Safety Data

• Hazardous Substances Data: 99010-24-9(Hazardous Substances Data)

Usage

Uses

Desamino Imiquimod is a pharmacologically active compound related to Imiquimod (I475000), an immune response modifier. It stimulates the production of Interferon-a.

InChI:InChI=1/C14H15N3/c1-10(2)8-17-9-16-13-7-15-12-6-4-3-5-11(12)14(13)17/h3-7,9-10H,8H2,1-2H3

Upstream product

• 64-18-6 formic acid 
• 1055720-75-6 4-isobutyl-3-amino quinoline 
• 878757-64-3 N'-(4-chloroquinolin-3-yl)-N,N-dimethylimidoformamide 
• 78-81-9 isobutylamine 
• 878757-58-5 N-(4-chloroquinolin-3-yl)formamide 
• 129377-66-8 3-amino-quinolin-4-ol; hydrochloride 
• 99010-09-0 3-Amino-4-(2-methylpropylamino)-quinoline 
• 122-51-0 orthoformic acid triethyl ester 
• 39061-97-7 4-chloro-3-nitroquinoline 
• 50332-66-6 3-nitro-quinolin-4-ol 
• 611-36-9 quinolin-4-ol 
• 99009-85-5 N-(2-methylpropyl)-3-nitro-4-quinolinamine 
• 14036-06-7 diethoxymethyl acetate 

Downstream Products

• 144875-74-1 α-butyl-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline-2-methanol 
• 144660-63-9 1-(2-methylpropyl)-α-phenyl-1H-imidazo[4,5-c]quinoline-2-methanol 
• 144660-62-8 N-benzoyl-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine 
• 144875-75-2 1-(1-isobutyl-1H-imidazo[4,5-c]quinolin-2-yl)pentyl acetate 
• 852802-29-0 1-{[3-(2-methyl-1,3-dioxolan-2-yl)propanoyl]oxy}pyrrolidine-2,5-dione 
• 852802-20-1 1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline-2-carbaldehyde 
• 896106-14-2 1-isobutyl-1H-imidazo-[4,5-c]-quinoline-5-N-oxide hydrochloride 
• 144875-58-1 α-methyl-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline-2-methanol 
• 144875-81-0 2-(2-methoxyethyl)-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline 
• 99011-02-6 imiqimod 
• 723283-87-2 1-(2-methylpropyl)-8-nitro-1H-imidazo[4,5-c]quinolin-4-amine 
• 723283-88-3 8-amino-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine 
• 723281-26-3 8-bromo-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine 
• 99010-64-7 4-Chloro-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline 

Relevant articles and documents

AMINE COMPOUNDS HAVING ANTI-INFLAMMATORY, ANTIFUNGAL, ANTIPARASITIC AND ANTICANCER ACTIVITY

Amine compounds having activity against inflammation, fungi, unicellular parasitic microorganisms, and cancer are described. The compounds contain a monocyclic, bicyclic, or tricyclic aromatic ring having one, two, or three ring nitrogen atoms.

A PROCESS FOR PREPARATION OF 4-AMINO-1-ISOBUTYL-1H-IMIDAZO[4,5-C]-QUINOLINE (IMIQUIMOD)

A process for preparation of imiquimod comprising oxidation of 1-Isobutyl-1H-imidazo quinoline quinoline (II) afforded 1-Isobutyl-lH- imidazo-[4,5-c]-quinoline-5-N-oxide (III) which is isolated in pure form as its hydrochloride salt (IV) followed by conversion to 4-chloro derivative(V) and conversion to corresponding 4-iodo derivative (VI) which is a new intermediate. This new intermediate is convened to imiquimod (VIII) and purified via its novel maleate salt.

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.