39217-91-9

Usage

Uses

Used in Pharmaceutical Industry:
5-NITRO-1,2,3,4-TETRAHYDRO-QUINOLINE HYDROCHLORIDE is used as an intermediate in the synthesis of quinoline derivatives for their potential applications in medicinal chemistry.
Used in Antimalarial Drug Synthesis:
5-NITRO-1,2,3,4-TETRAHYDRO-QUINOLINE HYDROCHLORIDE is used as a key component in the development of antimalarial drugs, contributing to the creation of effective treatments against malaria.
Used in Research and Development:
5-NITRO-1,2,3,4-TETRAHYDRO-QUINOLINE HYDROCHLORIDE is utilized as a building block in the research and development of new pharmaceuticals, facilitating the synthesis of diverse chemical compounds with biological activities.
Used in Organic Transformations:
Due to its high reactivity, 5-NITRO-1,2,3,4-TETRAHYDRO-QUINOLINE HYDROCHLORIDE is employed in various organic transformations, allowing for the creation of a wide range of chemical compounds with potential applications in different fields.

Upstream product

• 607-34-1 5-nitroquinoline 
• 635-46-1 1,2,3,4-tetrahydroisoquinoline 
• 22774-77-2 N-allyl-(3-nitrophenyl)amine 

Relevant academic research and scientific papers

Design, Synthesis, and Structure-Activity Relationships of Indoline-Based Kelch-like ECH-Associated Protein 1-Nuclear Factor (Erythroid-Derived 2)-Like 2 (Keap1-Nrf2) Protein-Protein Interaction Inhibitors

The Keap1 (Kelch-like ECH-associated protein 1)-Nrf2 (nuclear factor erythroid 2-related factor 2)-ARE (antioxidant response element) pathway is the major defending mechanism against oxidative stresses, and directly disrupting the Keap1-Nrf2 protein-protein interaction (PPI) has been an attractive strategy to target oxidative stress-related diseases, including cardiovascular diseases. Here, we describe the design, synthesis, and structure-activity relationships (SARs) of indoline-based compounds as potent Keap1-Nrf2 PPI inhibitors. Comprehensive SAR analysis and thermodynamics-guided optimization identified 19a as the most potent inhibitor in this series, with an IC50 of 22 nM in a competitive fluorescence polarization assay. Further evaluation indicated the proper drug-like properties of 19a. Compound 19a dose-dependently upregulated genes and protein level of Nrf2 as well as its downstream markers and showed protective effects against lipopolysaccharide-induced injury in both H9c2 cardiac cells and mouse models. Collectively, we reported here a novel indoline-based Keap1-Nrf2 PPI inhibitor as a potential cardioprotective agent.

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.

Synthesis method of 1, 2, 3, 4-tetrahydroquinoline compound

Belonging to the technical field of organic chemical synthesis, the invention discloses a synthesis method of a 1, 2, 3, 4-tetrahydroquinoline compound. The method adopts elemental iodine as the catalyst, uses borane as the reductant, and subjects a quinoline compound to catalytic reduction reaction, thus obtaining the product. Compared with the existing synthesis methods, the method has the greatest characteristics of use of cheap I2 as the catalyst, no need for metal to participate in reaction, mild reaction conditions, rapidity and high efficiency, high catalytic efficiency, simple operation, good selectivity, high product conversion rate up to 80% or more, is of great popularization and application value, and is beneficial to industrial production.

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.

Selective anti-markovnikov cyclization and hydrofluorination reaction in superacid HF/SbF5: A tool in the design of nitrogen-containing (fluorinated) polycyclic systems

The selective synthesis of tetrahydroquinolines and fluorinated arylamines was performed in superacid HF/SbF5 through a superelectrophilic ammonium-carbenium activation process. This anti-Markovnikov oriented reaction was applied to the straightforward synthesis of highly valued (fluorinated) nitrogen-containing heterocyclic compounds.

Anti-Markovnikov additions to N-allylic derivatives involving ammonium-carbenium superelectrophiles

Anti-Markovnikov additions to non-conjugated unsaturated amines in superacid are reported. In situ NMR studies, DFT calculations and labelled substrates reactions support the involvement of new ammonium-carbenium superelectrophiles in this original proces

Synthesis of complex ortho-allyliodoarenes by employing the reductive iodonio-claisen rearrangement

The reductive iodonio-Claisen rearrangement (RICR), involving complex aromatic λ3-iodanes and allyltrimethylsilane, was investigated. The RICR reaction of complex substituted aromatic hypervalent iodine (III) compounds and an allylmetal partner was conducted. The anionic oxy Cope rearrangement was found to be approximately 1010 to 1017 times faster than the neutral oxy Cope rearrangement due to weakening of the adjacent C-C bond by the oxygen anion. The results also indicate that the steric and electronic nature of the aromatic λ3-iodanes is the dominant factor influencing the [3,3]-sigmatropic rearrangement reaction. The removal of tert-butyl ether protecting group by using trifluroacetic acid in dichloromethane in the presence of triisopropylsilane gives the natural product broussin in 39% yield.

Synthesis of 6-nitro-1,2,3,4-tetrahydroquinoline: An experimental and theoretical study of regioselective nitration

A revision of the literature on the nitration of tetrahydroquinolines yielded a number of inconsistencies. Thus, we have carried out a thorough study on the nitration of tetrahydroquinoline and several of its N-protected derivatives both experimentally and at theoretical level. Usually, nitration is carried out in acidic conditions and, thus, tetrahydroquinoline would be N-protonated; however, if the amino group is protected, the neutral system will be the one undergoing nitration. Different protecting groups have been explored varying, not only electronic and steric effects, but also deprotection conditions. Additionally, different reagents and reaction conditions have been investigated. From this study we have been able to achieve total regioselectivity for nitration at the 6-position. A very detailed NMR study has been carried out to unequivocally characterise the four nitro isomers. In parallel, a computational study has been performed that is in agreement with the experimental results obtained. With this purpose, all the σ complexes of the four nitro isomers neutral and N-protonated have been optimized both in gas and water condensed phases by using the B3LYP/6-31++G* level of computation. The selective nitration of tetrahydroquinoline was studied. N-Protecting groups presence or absence directs nitration at different positions. Regioselective nitration at 6-position was achieved. A DFT computational study of all nitro σ complexes was performed in gas and water phases, the results are consistent with the experiments. Copyright

N-Tetrahydroquinolinyl, N-quinolinyl and N-isoquinolinyl biaryl carboxamides as antagonists of TRPV1

Starting from the high throughput screening hit (3), novel N-tetrahydroquinolinyl, N-quinolinyl and N-isoquinolinyl carboxamides have been identified as potent antagonists of the ion channel TRPV1. The N-quinolinylnicotinamide (46) showed excellent potenc

Regio- and chemoselective transfer hydrogenation of quinolines catalyzed by a Cp*Ir complex

An efficient method for the transfer hydrogenation of quinolines catalyzed by a Cp*Ir complex was developed. A variety of 1,2,3,4-tetrahydroquinolines were obtained by regio- and chemoselective transfer hydrogenation of quinolines using 2-propanol as a hydrogen source.