22246-16-8

Usage

Uses

Used in Pharmaceutical Industry:
3,4-Dihydro-6-nitro-2(1H)-quinolinone is used as a key intermediate for the synthesis of triazolyl dihydroquinoliinones, which possess anticonvulsant and antidepressant activities. Its role in the development of these compounds is crucial, as it contributes to the overall effectiveness of the final products in treating epilepsy and depression.
In addition to its application in the pharmaceutical industry, 3,4-Dihydro-6-nitro-2(1H)-quinolinone may also find use in other industries where organic synthesis is required, such as the chemical and materials science fields.

InChI:InChI=1/C9H8N2O3/c12-9-4-1-6-5-7(11(13)14)2-3-8(6)10-9/h2-3,5H,1,4H2,(H,10,12)

Upstream product

• 553-03-7 3,4-dihydro-2(1H)-quinolone 
• 7664-93-9 sulfuric acid 
• 7697-37-2 nitric acid 
• 62-53-3 aniline 
• 3460-04-6 3-chloro-N-phenylpropionamide 

Downstream Products

• 22246-13-5 6-amino-3,4-dihydro-1H-quinolin-2-one 
• 296759-27-8 6,8-dinitro-3,4-dihydroquinolin-2-one 
• 77372-73-7 6-nitroquipazine 
• 99139-81-8 N-(2-oxo-1,2,3,4-tetrahydro-[6]quinolyl)-benzamide 
• 64495-55-2 6-nitroquinolin-2-ol 
• 1063406-38-1 1-(4-methoxybenzyl)-6-nitro-3,4-dihydroquinolin-2(1H)-one 

Relevant academic research and scientific papers

Novel 3,4-dihydroquinolin-2(1H)-one derivatives as dual inhibitor targeting AKR1B1/ROS for treatment of diabetic complications: Design, synthesis and biological evaluation

AKR1B1 (Aldose reductase) has been used as therapeutic intervention target for treatment of diabetic complications over 50 years, and more recently for inflammation and cancer. However, most developed small molecule inhibitors have the defect of low bioac

Synthesis and Exploration of Abscisic Acid Receptor Agonists Against Dought Stress by Adding Constraint to a Tetrahydroquinoline-Based Lead Structure

New oxotetrahydroquinolinyl- and oxindolinyl sulfonamides interacting with RCAR/(PYR/PYL) receptor proteins were identified as lead structures against drought stress in crops starting from protein docking studies of a sulfonamide lead structure, followed by in-depth SAR studies. Optimized five to six step synthetic approaches via substituted amino oxo-tetrahydro-quinolines and amino oxo-indolines as essential intermediates gave access to the envisaged oxo-tetrahydroquinolinyl and oxindolinyl sulfonamides. Whilst oxo-tetrahydroquinolinyl sulfonamides with additional carbon substituents or spiro-cycloalkyl groups exhibited only low to moderate target affinities, the corresponding spiro-oxindolinyl and oxo-tetrahydroquinolinyl sulfonamides carrying optimized N-substituents revealed strong interactions with RCAR/(PYR/PYL) receptor proteins in Arabidopsis thaliana. Remarkably, the in vitro activity observed for these new compounds was on the same level as observed for the naturally occurring plant hormone in line with strong efficacy against drought stress in-vivo (canola and wheat as broad-acre crops).

Tetrahydroquinolinyl phosphinamidates and phosphonamidates enhancing tolerance towards drought stress in crops via interaction with ABA receptor proteins

New phosphorous-containing lead structures against drought stress in crops interacting with RCAR/(PYR/PYL) receptor proteins were identified starting from in-depth SAR studies of related sulfonamide lead structures and protein docking studies. A converging 6-step synthesis via phosphinic chlorides and phosphono chloridates as key intermediates afforded envisaged tetrahydroquinolinyl phosphinamidates and phosphonamidates. Whilst tetrahydroquinolinyl phosphonamidates 13a,b exhibited low to moderate target affinities, the corresponding tetrahydroquinolinyl phosphinamidates 12a,b revealed confirmed strong affinities for RCAR/ (PYR/PYL) receptor proteins in Arabidopsis thaliana on the same level as essential plant hormone abscisic acid (ABA) combined with promising efficacy against drought stress in vivo (broad-acre crops wheat and canola).

Preparation method of 6-hydroxy-3,4-dihydro-2(1H)quinolinone

The invention belongs to the field of preparation of intermediates in chemical engineering, and particularly relates to a preparation method of 6-hydroxy-3,4-dihydro-2(1H)quinolinone. The preparationmethod comprises the following steps of using aniline and 3-chloropropionyl chloride as raw materials; performing cyclization, nitrification, reduction and diazotization hydrolysis, so as to synthesize the target product, namely 6-hydroxy-3,4-dihydro-2(1H)quinolinone. The preparation method has the advantages that the reaction conditions are mild, the cost is reduced, and the yield rate is increased.

SUBSTITUTED OXOTETRAHYDROQUINOLINYLPHOSPHINIC ACID AND PHOSPHINIC ACID AMIDES OR SALTS THEREOF AND USE THEREOF TO INCREASE STRESS TOLERANCE IN PLANTS

The invention relates to substituted oxotetrahydroquinolinylphosphin- and -phosphonamides of the general formula (I) and salts thereof where the radicals of the formula (I) are each as defined in the description for enhancing stress tolerance in plants to abiotic stress, and for enhancing plant growth and/or for increasing plant yield.

USE OF SUBSTITUTE OXO TETRAHYDROQUINOLINE SULFONAMIDES OR SALTS THEREOF FOR RAISING STRESS TOLERANCE OF PLANTS

The invention relates to the use of substituted oxotetrahydroquinolinylsulfonamides or salts thereof where the radicals in the general formula (I) correspond to the definitions given in the description, for enhancing stress tolerance in plants to abiotic stress, and/or for increasing plant yield.

COMPOUNDS FOR REGULATING FAK AND/OR SRC PATHWAYS

The present application provides novel optionally substituted fused pyridine and pyrimidine bicyclic compounds and pharmaceutically acceptable salts thereof. Also provided are methods for preparing these compounds. These compounds are useful in co-regulating FAK and/or Src activity by administering a therapeutically effective amount of one or more of the compounds to a subject. By doing so, these compounds are effective in treating conditions associated with the dysregulation of the FAK and/or Src pathway. Advantageously, these compounds perform as dual FAK and/or Src inhibitors. A variety of conditions can be treated using these compounds and include diseases which are characterized by inflammation or abnormal cellular proliferation. In one embodiment, the disease is cancer.

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,

Aminoluciferins extend firefly luciferase bioluminescence into the near-infrared and can be preferred substrates over d-luciferin

Firefly luciferase adenylates and oxidizes D-luciferin to chemically generate visible light and is widely used for biological assays and imaging. Here we show that both luciferase and luciferin can be reengineered to extend the scope of this light-emitting reaction. D-Luciferin can be replaced by synthetic luciferin analogues that increase near-infrared photon flux >10-fold over that of D-luciferin in live luciferase-expressing cells. Firefly luciferase can be mutated to accept and utilize rigid aminoluciferins with high activity in both live and lysed cells yet exhibit 10 000-fold selectivity over the natural luciferase substrate. These new luciferin analogues thus pave the way to an extended family of bioluminescent reporters.

Design, synthesis and evaluation of the antidepressant and anticonvulsant activities of triazole-containing quinolinones

A series of 1-substituted-6-(4H-1,2,4-triazol-4-yl)-3,4-dihydroquinolin- 2(1H)-ones were designed, synthesized, and screened for their antidepressant and anticonvulsant activities. Interestingly, compounds 5i, 5j, 5m, and 5n led to significant reductions in the immobility time in the forced swimming test at a dose of 50 mg/kg, and exhibited higher levels of efficacy than the reference standard fluoxetine. In addition, compound 5i exhibited greater efficacy than fluoxetine in the tail suspension test. The results of an open field test further confirmed that compound 5i provided a good antidepressant effect. In the maximal electroshock seizure screen, compounds 5c and 5d showed moderate levels of anticonvulsant activity and protected 100% of the animals at a dose of 100 mg/kg. None of the synthesized compounds showed any neurotoxicity in the rotarod test at a dose of 100 mg/kg.