14026-45-0

Usage

Uses

Used in Pharmaceutical Industry:
6-Nitro-1,2,3,4-tetrahydroquinoline is used as an intermediate in the synthesis of various pharmaceuticals for its potential biological and pharmacological activities. It contributes to the development of new drugs due to its antimicrobial and antitumor properties.
Used in Organic Synthesis:
6-Nitro-1,2,3,4-tetrahydroquinoline is used as a building block in the synthesis of organic molecules, playing a crucial role in the creation of complex organic compounds for various applications in the chemical industry.
Used in Antimicrobial Applications:
6-Nitro-1,2,3,4-tetrahydroquinoline is employed for its antimicrobial properties, serving as a key component in the development of antimicrobial agents to combat various types of infections.
Used in Antitumor Applications:
6-Nitro-1,2,3,4-tetrahydroquinoline is utilized in the development of antitumor agents, leveraging its potential to inhibit tumor growth and contribute to cancer treatment strategies.

InChI:InChI=1/C9H10N2O2/c12-11(13)8-3-4-9-7(6-8)2-1-5-10-9/h3-4,6,10H,1-2,5H2

Upstream product

• 4169-19-1 1-acetyl-1,2,3,4-tetrahydroquinoline 
• 613-50-3 6-nitroquinoline 
• 767-92-0 decahydroquinoline 
• 635-46-1 1,2,3,4-tetrahydroisoquinoline 
• 924829-59-4 6-nitro-N-pivaloyl-1,2,3,4-tetrahydroquinoline 
• 1290608-21-7 2,2,2-trifluoro-1-(6-nitro-3,4-dihydro-2H-quinolin-1-yl)ethanone 
• 1290608-23-9 (9H-fluoren-9-yl) methyl-3,4-dihydroquinoline-1(2H)-carboxylate 
• 1290608-22-8 (9H-fluoren-9-yl) methyl-6-nitro-3,4-dihydroquinoline-1(2H)-carboxylate 
• 14026-46-1 1-(1,2,3,4-tetrahydro-6-nitroquinolinyl)ethanone 
• 79066-90-3 2,2,2-trifluoro-1-(3,4-dihydroquinolin-1(2H)-yl)ethanone 
• 4138-40-3 N-allyl-p-nitroaniline 
• 22246-16-8 6-nitro-3,4-dihydro-1H-quinolin-2-one 
• 3460-04-6 3-chloro-N-phenylpropionamide 
• 62-53-3 aniline 

Downstream Products

• 30450-57-8 (6-nitro-3,4-dihydroquinolin-1(2H)-yl)(phenyl)methanone 
• 103796-41-4 6-amino-1,2,3,4-tetrahydroquinoline 
• 123296-53-7 8-Nitro-5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1,2-dione 
• 123296-82-2 6-nitro-1,2,3,4-tetrahydroquinoline-8-carboxylic acid 
• 857759-22-9 (6-amino-3,4-dihydroquinolin-1(2H)-yl)(phenyl)methanone 
• 860194-43-0 (1-benzoyl-1,2,3,4-tetrahydro-[6]quinolyl)-hydrazine 
• 613-50-3 6-nitroquinoline 
• 186390-79-4 6-Nitro-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester 
• 164148-92-9 tert-butyl 6-amino-3,4-dihydroisoquinoline-2(1H)-carboxylate 
• 14026-46-1 1-(1,2,3,4-tetrahydro-6-nitroquinolinyl)ethanone 

Relevant academic research and scientific papers

Design and development of Tetrahydro-Quinoline derivatives as dual mTOR-C1/C2 inhibitors for the treatment of lung cancer

Lung cancer is one of the most prevailed cancer worldwide. Many genes get mutated in lung cancer but the involvement of EGFR, KRAS, PTEN and PIK3CA are more common. Unavailability of potent drugs and resistance to the available drugs are major concern in

Utilization of renewable formic acid from lignocellulosic biomass for the selective hydrogenation and/or N-methylation

Lignocellulosic biomass is one of the most abundant renewable sources in nature. Herein, we have developed the utilization of renewable formic acid from lignocellulosic biomass as a hydrogen source and a carbon source for the selective hydrogenation and further N-methylation of various quinolines and the derivatives, various indoles under mild conditions in high efficiencies. N-methylation of various anilines is also developed. Mechanistic studies indicate that the hydrogenation occurs via a transfer hydrogenation pathway.

Method for selective catalytic hydrogenation of aromatic heterocyclic compounds in non-hydrogen participation manner

The invention discloses a method for selective catalytic hydrogenation of aromatic heterocyclic compounds in a non-hydrogen participation manner. The method comprises the following steps: by taking 1, 5-cyclooctadiene iridium chloride dimer as a catalyst and phenylsilane as a hydrogen source, carrying out stirring reaction under mild conditions without adding a ligand, namely catalytically hydrogenating the aromatic heterocyclic compounds to obtain hydrogenated products of the aromatic heterocyclic compounds. The method has the advantages of low cost, mild reaction conditions, high selectivity and the like, and special equipment such as a high-pressure kettle and the like and high-temperature conditions which are required when hydrogen is used are avoided.

Boric acid catalyzed chemoselective reduction of quinolines

Boric acid promoted transfer hydrogenation of substituted quinolines to synthetically versatile 1,2,3,4-tetrahydroquinolines (1,2,3,4-THQs) was described under mild reaction conditions using a Hantzsch ester as a mild organic hydrogen source. This methodology is practical and efficient, where isolated yields are excellent and reducible functional groups are well tolerated in the N-heteroarene moiety. The reaction parameters and tentative mechanistic pathways are demonstrated by various control experiments and NMR studies. The present work can also be scaled up to obtain gram quantities and the utility of the developed process is illustrated by the transformation of 1,2,3,4-THQs into a series of biologically important molecules including the antiarrhythmic drug nicainoprol.

Activation of Quinolines by Cationic Chalcogen Bond Donors

The application of already established as well as novel selenium- and sulfur-based cationic chalcogen bond donors in the catalytic activation of quinoline derivatives is presented. In the presence of selected catalysts, rate accelerations of up to 2300 compared to virtually inactive reference compounds are observed. The catalyst loading can be reduced to 1 molpercent while still achieving nearly full conversion for electron-poor and electron-rich quinolines. Contrary to expectations, preorganized catalysts were less active than the more flexible variants.

Iodine catalyzed reduction of quinolines under mild reaction conditions

A reduction of quinolines to synthetically versatile tetrahydroquinoline molecules with I2 and HBpin is described. In the presence of iodine (20 mol%) as a catalyst, reduction of quinolines and other N-heteroarenes proceeded readily with hydroboranes as the reducing reagents. The broad functional-group tolerance, good yields and mild reaction conditions imply high practical utility.

Recyclable Silica-Supported Iridium Catalysts for Selective Reductive Transformation of Quinolines with Formic Acid in Water

Mesoporous silica (SBA-15)-supported iridium catalysts are prepared by grafting of the newly developed cyclometalated iridium 2-aryl benzoxazole complexes with 3-(triethoxysilyl)-propyl-isocyanate (TEPIC) as a linker. The supported catalysts are characterized by solid-state NMR spectroscopy, small-angle X-ray scattering (SAXS), nitrogen physisorption, FTIR spectroscopy, and electron microscopy analysis, which indicate that the coordination environment of the iridium center as well as the two-dimensional hexagonal pore structure of SBA-15 is maintained after the immobilization. These supported catalysts have been successfully applied to the selective transfer hydrogenation of quinoline derivatives to 1,2,3,4-tetrahydroquinolines (THQs) with formic acid in pure water. Moreover, by simply adapting the amount of formic acid used, N-formyltetrahydroquinolines (FTHQs) could be selectively synthesized from quinolines in two-step, one-pot transfer hydrogenation/N-formylation reactions with these supported catalysts. Notably, these supported catalysts showed better catalytic reactivity than their homogeneous analogs, and they can be easily reused 12 times in the transformation of quinoline to N-formyltetrahydroquinoline (FTHQ) without significant loss of activity.

High efficient iron-catalyzed transfer hydrogenation of quinolines with Hantzsch ester as hydrogen source under mild conditions

A highly efficient transfer hydrogenation of quinolines with Hantzsch ester as hydrogen source in the presence of 1 mol% Fe(OTf)2 under mild conditions has been developed. A series of substituted 1,2,3,4-tetrahydroquinoline derivatives were afforded in excellent yields with good functional group tolerance.

Catalysis with chalcogen bonds: Neutral benzodiselenazole scaffolds with high-precision selenium donors of variable strength

The benzodiselenazoles (BDS) introduced in this report fulfill, for the first time, all the prerequisites for non-covalent high-precision chalcogen-bonding catalysis in the focal point of conformationally immobilized σ holes on strong selenium donors in a neutral scaffold. Rational bite-angle adjustment to the long Se-C bonds was the key for BDS design. For the unprecedented BDS motif, synthesis of 12 analogs from o-xylene, crystal structure, σ hole variation strategies, optoelectronic properties, theoretical and experimental anion binding as well as catalytic activity are reported. Chloride binding increases with the depth of the σ holes down to KD = 11 μM in THF. Catalytic activities follow the same trend and culminate in rate enhancements for transfer hydrogenation of quinolines beyond 100000.

A COMPOUND AND PHARMACEUTICAL COMPOUND FOR TREATMENT OF INFLAMMATORY DISEASES

The present invention relates to a pharmaceutical composition for treating inflammatory diseases, comprising: a compound represented by chemical formula I, a pharmaceutically acceptable salt thereof; a hydrate thereof; or a compound as a solvate thereof,