23833-99-0

Usage

Uses

Used in Pharmaceutical Industry:
4-CHLORO-8-NITROQUINOLINE is used as a building block for the synthesis of various bioactive compounds and drug candidates. Its unique structure and properties make it a valuable component in the development of new pharmaceuticals.
Used in Antimicrobial and Antifungal Applications:
4-CHLORO-8-NITROQUINOLINE is used as an antimicrobial and antifungal agent, demonstrating efficacy against a range of pathogens. Studies have shown its potential to combat various microorganisms, making it a promising candidate for use in antimicrobial and antifungal treatments.
Used in Materials Science:
4-CHLORO-8-NITROQUINOLINE is used in the development of new materials due to its unique electronic and optical properties. Its potential applications in materials science include the creation of advanced materials with specific properties for various industries.
Used in Organic Electronic Devices:
4-CHLORO-8-NITROQUINOLINE is used in the research and development of organic electronic devices. Its electronic and optical characteristics make it a valuable component in the design and fabrication of innovative electronic devices with improved performance and functionality.

Upstream product

• 23833-95-6 8-nitro-4(1H)-quinolinone 
• 529-37-3 4(1H)-quinolinone 
• 551-93-9 2-aminoacetophenone 
• 611-35-8 4-chloroquinoline 
• 56-57-5 4-nitroquinoline-N-oxide 
• 25063-47-2 2,2-dimethyl-5-(((2-nitrophenyl)amino)methylene)-1,3-dioxane-4,6-dione 
• 88-74-4 2-nitro-aniline 
• 611-36-9 quinolin-4-ol 
• 132664-49-4 8-acetyl-3-ethoxycarbonyl-1,4-dihydro-4-oxoquinoline 
• 83475-06-3 8-nitro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid 
• 7664-93-9 sulfuric acid 
• 7697-37-2 nitric acid 
• 194784-10-6 acetic acid-(2-acetyl-6-nitro-anilide) 
• 68-12-2 N,N-dimethyl-formamide 

Downstream Products

• 89770-28-5 4-methoxy-8-nitroquinoline 
• 363609-03-4 8-nitro-4-phenoxy-quinoline 
• 578-66-5 8-amino quinoline 
• 23432-46-4 8-nitro-quinolin-4-ol 
• 89770-26-3 8-nitro-[4]quinolylamine 
• 81764-16-1 4-chloro-8-aminoquinoline 
• 53867-98-4 4,8-Diaminochinolin 
• 59665-93-9 4-methoxyquinoline-8-amine 

Relevant academic research and scientific papers

Synthesis of quinolinylaminopyrimidines and quinazolinylmethylaminopyrimidines with antiproliferative activity against melanoma cell line

Synthesis of a new series of quinolinylaminopyrimidines 1a-k and quinazolinylmethylaminopyrimidines 2a-i containing aminoquinoline and aminoquinazoline as hinge regions is described. Their in vitro antiproliferative activities against A375P human melanoma cell line were tested. Among them, compounds 1h and 1k exhibited the highest antiproliferative activities against A375P cell line with IC50 values in sub-micromolar scale. Compounds 1i, 2b and 2g showed similar potency against A375P to Sorafenib as a reference compound. The representative compound 1h showed high, dose-dependent inhibition of MEK and ERK kinases.

Direct amination of nitroquinoline derivatives via nucleophilic displacement of aromatic hydrogen

The vicarious nucleophilic substitution of hydrogen (VNS) reaction in electron-deficient nitroquinolines was studied. Properties of all new products have been characterized by several techniques: MS, HRMS, FTIR, GC-MS, electronic absorption spectroscopy, and multinuclear NMR. The structures of 4-chloro-8-nitroquinoline, 8-(tert-butyl)-2-methyl-5-nitroquinoline, 9-(8nitroquinolin-7-yl)-9H-carbazole and (Z)-7-(9H-carbazol-9-yl)-8-(hydroxyimino)quinolin-5(8H)-one were determined by single-crystal X-ray diffraction measurements. The 9-(8-nitroquinolin-7-yl)9H-carbazole and (Z)-7-(9H-carbazol-9-yl)-8-(hydroxyimino)quinolin-5(8H)-one illustrate the nitro/nitroso conversion within VNS reaction. Additionally, 9-(8-isopropyl-2-((8-isopropyl-2-methyl5-nitroquinolin-6-yl)methyl)-5-nitrosoquinolin-6-yl)-9H-carbazole is presented as a double VNS product. It is postulated that the potassium counterion interacts with the oxygen on the nitro group, which could influence nucleophile attack in that way.

Toll-like receptor-7 small molecule inhibitor and preparation method thereof

The invention belongs to the field of chemical small molecules, and particularly relates to a Toll-like receptor-7 small molecule inhibitor. The invention provides the Toll-like receptor-7 small molecule inhibitor, which takes a co-inhibitor of TLR7 and TLR8 obtained by screening as a research object, realizes selective regulation and control of TLR7 and TLR8 through the research on the structureoptimization and structure-activity relationship (SAR) of a parent compound, and further develops a high-efficiency, non-toxic and specific small molecule inhibitor with certain selectivity on TLR 7.The TLR7 small molecule inhibitor has a certain effect and potential medicinal value in autoimmune diseases (systemic lupus erythematosus).

Effects of the Distance between Radical Sites on the Reactivities of Aromatic Biradicals

Coupling of the radical sites in isomeric benzynes is known to hinder their radical reactivity. In order to determine how far apart the radical sites must be for them not to interact, the gas-phase reactivity of several isomeric protonated (iso)quinoline-and acridine-based biradicals was examined. All the (iso)quinolinium-based biradicals were found to react slower than the related monoradicals with similar vertical electron affinities (i.e., similar polar effects). In sharp contrast, the acridinium-based biradicals, most with the radical sites farther apart than in the (iso)quinolinium-based systems, showed greater reactivities than the relevant monoradicals with similar vertical electron affinities. The greater distances between the two radical sites in these biradicals lead to very little or no spin-spin coupling, and no suppression of radical reactivity was observed. Therefore, the radical sites can still interact if they are located on adjacent benzene rings and only after being separated further than that does no coupling occur. The most reactive radical site of each biradical was experimentally determined to be the one predicted to be more reactive based on the monoradical reactivity data. Therefore, the calculated vertical electron affinities of relevant monoradicals can be used to predict which radical site is most reactive in the biradicals.

Visible-Light-Photocatalyzed Reductions of N-Heterocyclic Nitroaryls to Anilines Utilizing Ascorbic Acid Reductant

A photoreductive protocol utilizing [Ru(bpy)3]2+ photocatalyst, blue light LEDs, and ascorbic acid (AscH2) has been developed to reduce nitro N-heteroaryls to the corresponding anilines. Based on experimental and computational results and previous studies, we propose that the reaction proceeds via proton-coupled electron transfer between AscH2, photocatalyst, and the nitro N-heteroaryl. The method offers a green catalytic procedure to reduce, e.g., 4-/8-nitroquinolines to the corresponding aminoquinolines, substructures present in important antimalarial drugs.

Synthesis of 4,5-bis(dimethylamino)quinolines and the dual direction of their protonation

A study on the synthesis of derivatives of 4,5-bis(dimethylamino)quinoline, which is a quinoline analog of 1,8-bis(dimethylamino)naphthalene (also known by its trade name Proton Sponge) was carried out. The first two representatives of this series were obtained. Depending on the aggregate state, solvent, and structural features, these compounds may be protonated either at the quinoline heteroatom or peri-NMe2 groups.

BICYCLIC COMPOUNDS AS mPGES-1 INHIBITORS

The present disclosure is directed to compounds of formula (I), and pharmaceutically acceptable salts thereof, as mPGES-1 inhibitors. These compounds are inhibitors of the microsomal prostaglandin E synthase-1 (mPGES-1) enzyme and are therefore useful in the treatment of pain and/or inflammation from a variety of diseases or conditions, such as asthma, osteoarthritis, rheumatoid arthritis, acute or chronic pain and neurodegenerative diseases.

Novel quinolinylaminoisoquinoline bioisosteres of sorafenib as selective RAF1 kinase inhibitors: Design, synthesis, and antiproliferative activity against melanoma cell line

Design and synthesis of a new series of quinolinylaminoisoquinoline derivatives as conformationally restricted bioisosteres of Sorafenib are described. Their in vitro antiproliferative activity against A375P melanoma cell line was tested. Compounds 1b, 1d, 1g, and 1j showed the highest potency against A375P cell line with IC50 values in sub-micromolar scale. In addition, compound 1d exerted high selectivity towards RAF1 serine/threonine kinase with 96.47% inhibition at 10 μM, and IC50 of 0.96 μM. This compound can possess antiproliferative activity against melanoma cells through inhibition of RAF1 kinase.

AMINOQUINOLINE DERIVATIVES, PREPARATION METHOD THEREOF AND PHARMACEUTICAL COMPOSITION COMPRISING THE SAME

Provided are a novel aminoquinoline compound represented by Formula 1 or a pharmaceutically acceptable salt thereof, preparation method thereof, and a pharmaceutical composition for preventing or treating cutaneous cancer, comprising the aminoquinoline co

Aminoquinoline derivatives with antiproliferative activity against melanoma cell line

The synthesis of a novel series of aminoquinoline derivatives 1a-p and their antiproliferative activities against A375 human melanoma cell line were described. Most compounds showed superior antiproliferative activities to Sorafenib as a reference compoun