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Usage

Uses

Used in Pharmaceutical Industry:
2-Chloro-N-(2-methylpropyl)-3-nitroquinolin-4-amine is used as an intermediate compound for the synthesis of amine compounds with various therapeutic properties. Its presence in these compounds contributes to their anti-inflammatory, antifungal, antiparasitic, and anticancer activities, making it a crucial component in the development of new medications for a wide range of diseases and conditions.
Used in Preparation of Imiquimod:
2-Chloro-N-(2-methylpropyl)-3-nitroquinolin-4-amine is also utilized in the preparation of Imiquimod, a drug derived from dihydroxyquinoline. Imiquimod is known for its immunomodulatory and antiviral properties, and is commonly used in the treatment of external genital and anal warts, actinic keratosis, and superficial basal cell carcinoma. 2-chloro-N-(2-methylpropyl)-3-nitroquinolin-4-amine plays a vital role in the synthesis process, ensuring the effectiveness of the final product.

InChI:InChI=1/C13H14ClN3O2/c1-8(2)7-15-11-9-5-3-4-6-10(9)16-13(14)12(11)17(18)19/h3-6,8H,7H2,1-2H3,(H,15,16)

Upstream product

• 15151-57-2 2,4-dihydroxy-3-nitroquinoline 
• 70254-44-3 2,4-dihydroxyquinoline 
• 15151-57-2 4-hydroxy-3-nitro-1,2-dihydroquinolin-2-one 
• 78-81-9 isobutylamine 
• 132521-66-5 2,4-dichloro-3-nitroquinoline 

Downstream Products

• 133860-76-1 2-chloro-N⁴-(2-methylpropyl)quinoline-3,4-diamine 
• 1025814-34-9 N-(2-chloro-4-isobutylamino-quinolin-3-yl)-2-phenoxy-acetamide 
• 99011-02-6 imiqimod 
• 1508303-97-6 5-chloro-2-[(1-isobutyl-1H-imidazo[4,5-c]quinolin-4-yl)amino]benzoic acid 
• 1508303-98-7 5-iodo-2-[(1-isobutyl-1H-imidazo[4,5-c]quinolin-4-yl)amino]benzoic acid 
• 1508303-93-2 2-[(1-isobutyl-1H-imidazo[4,5-c]quinolin-4-yl)amino]benzoic acid 
• 1508303-94-3 3-bromo-2-[(1-isobutyl-1H-imidazo[4,5-c]quinolin-4-yl)amino]benzoic acid 
• 1508303-95-4 5-bromo-2-[(1-isobutyl-1H-imidazo[4,5-c]quinolin-4-yl)amino]benzoic acid 
• 1508303-96-5 4-chloro-2-[(1-isobutyl-1H-imidazo[4,5-c]quinolin-4-yl)amino]benzoic acid 

Relevant academic research and scientific papers

Synthesis of [1,2,4]triazolo[4,3-a]quinoxaline-1,3,4-oxadiazole derivatives as potent antiproliferative agents via a hybrid pharmacophore approach

Imiquimod (1-isobutyl-1H-imidazo[4,5-c]quinolin-4-amine) is efficacious in topical therapy for certain types of skin cancers. Structurally similar EAPB0203 (N-methyl-1-(2-phenethyl)imidazo[1,2-a]quinoxalin-4-amine) has been shown higher in vitro potency than imiquimod. Besides, triazole, oxadiazole, and thiadiazole rings are privileged building blocks in drug design. A series of [1,2,4]triazolo[4,3-a]quinoxaline-1,3,4-oxadiazole and [1,2,4]triazolo[4,3-a]quinoxaline-1,3,4-thiadiazole derivatives were therefore synthesized by incorporation of these rings into the structure of EAPB0203 and assessed their antiproliferative effects against various cancer cell lines. The 1,3,4-oxadiazole derivatives demonstrated the superior effectiveness compared to imiquimod and EAPB0203. Our findings highlight the excellent potential of [1,2,4]triazolo[4,3-a]quinoxaline-1,3,4-oxadiazole derivatives as anticancer agents.

Synthesis of azabicyclo[4.2.0]octa-1,3,5-trien-8-one analogues of 1H-imidazo[4,5-c]quinoline and evaluation of their antimicrobial and anticancer activities

In search of new and efficient antimicrobial and anticancer agents based on the imidazoquinoline structural framework, a series of novel 7-(1-isobutyl-1H-imidazo[4,5-c]quinolin-4-yl)-7-Azabicyclo[4.2.0]octa-1,3, 5-trien-8-ones (8a-f) were synthesized from the corresponding 2,4-dihydroxoquinoline derivative through multistep reactions. The structures of these compounds were established by IR, 1H NMR, 13C NMR and mass spectral studies. The 7-(1-isobutyl-1H-imidazo[4,5-c]quinolin-4-yl)-7- Azabicyclo[4.2.0]octa-1,3,5-trien-8-one (8a-f) analogues were evaluated for their in vitro antimicrobial activity by serial dilution method minimum inhibitory concentration (MIC). The derivatives 8c, 8e and 8f exhibited excellent antibacterial activity comparable to the parent drug ampicillin with MIC value. Compounds 7a-f and 8a-f were also assessed for their cytotoxic activity (IC50) against HeLa cells using the Trypan blue exclusion assay method. The compounds 7c and 8b displayed potential anticancer activity. In a molecular docking study, these compounds showed minimum binding energy and good affinity towards the active pocket. They are believed to be good inhibitors of β-tubulin. The results of these studies provided evidence that 7-(1-isobutyl-1H-imidazo[4,5-c]quinolin-4-yl)-7-Azabicyclo[4.2.0]octa-1,3, 5-trien-8-one (8a-f) derivatives are a promising class of antibacterial and anticancer agents.

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.

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.

3-Amino or 3-nitro quinoline compounds which are intermediates in preparing 1H-imidazo[4,5-c]quinolines

A process for the preparation of 1-substituted, 4-substituted-1H-imidazo[4,5-c]quinolines, intermediates in the preparation of such compounds, and processes for the preparation of such intermediates.