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

Description

1-(2-METHYLPROPYL)-1H-IMIDAZO[4,5-C]QUINOLINE, also known as Desamino Imiquimod, is a pharmacologically active compound that is structurally related to Imiquimod, an immune response modifier. It possesses the ability to stimulate the production of Interferon-a, which plays a crucial role in the immune system's response to various stimuli.

Uses

Used in Pharmaceutical Industry:
1-(2-METHYLPROPYL)-1H-IMIDAZO[4,5-C]QUINOLINE is used as an immune response modifier for its ability to stimulate the production of Interferon-a. This makes it a potential candidate for the development of therapeutic agents targeting various diseases and conditions where modulation of the immune response is required.
Used in Immunotherapy:
In the field of immunotherapy, 1-(2-METHYLPROPYL)-1H-IMIDAZO[4,5-C]QUINOLINE is used as a compound to enhance the body's natural immune response against diseases such as cancer. Its ability to stimulate Interferon-a production can contribute to the development of novel immunotherapeutic strategies for cancer treatment and other immune-related disorders.
Used in Research and Development:
1-(2-METHYLPROPYL)-1H-IMIDAZO[4,5-C]QUINOLINE is also utilized in research and development settings to study the mechanisms of immune response modulation and to develop new drugs and therapies based on its pharmacological properties. Its role in Interferon-a production makes it a valuable tool for understanding the complex interactions between the immune system and various diseases.

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

• 99010-09-0 3-Amino-4-(2-methylpropylamino)-quinoline 
• 122-51-0 orthoformic acid triethyl ester 
• 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 
• 64-18-6 formic acid 
• 1055720-75-6 4-isobutyl-3-amino quinoline 
• 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 
• 144875-81-0 2-(2-methoxyethyl)-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline 
• 144875-58-1 α-methyl-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 
• 852800-40-9 C₃₀H₃₂N₈O₂ 
• 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 
• 144660-62-8 N-benzoyl-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine 
• 896106-14-2 1-isobutyl-1H-imidazo-[4,5-c]-quinoline-5-N-oxide hydrochloride 
• 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 

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.