64495-55-2

Usage

Uses

Used in Pharmaceutical Industry:
2(1H)-Quinolinone, 6-nitrois used as an intermediate in the synthesis of various pharmaceuticals for its strong biological activity and potential as a cytotoxic and antitumor agent. It plays a crucial role in the development of new drugs for the treatment of various diseases, including cancer.
Used in Agrochemical Industry:
In the agrochemical industry, 2(1H)-Quinolinone, 6-nitroserves as an intermediate in the synthesis of various agrochemicals, contributing to the development of effective pest control agents and other agricultural products.
Used as a Dye Intermediate:
2(1H)-Quinolinone, 6-nitrois used as a dye intermediate in the production of various dyes, which find applications in different industries such as textiles, plastics, and printing inks.
Used in Specialty Chemicals Production:
2(1H)-Quinolinone, 6-nitrois utilized in the production of specialty chemicals, which have unique properties and are used in specific applications across various industries.
Used in Corrosion Inhibition:
6-nitro-2(1H)-quinolinone has been investigated for its potential as a corrosion inhibitor in various industrial applications, offering protection to metal surfaces and equipment from corrosion and extending their service life.
Overall, 2(1H)-Quinolinone, 6-nitrois a versatile compound with a wide range of applications across different industries, making it a valuable asset for researchers and professionals in the fields of medicinal chemistry, organic synthesis, and materials science.

Upstream product

• 49609-07-6 2-amino-6-nitroquinoline 
• 29969-57-1 2-chloro-6-nitroquinoline 
• 13675-92-8 6-nitroquinoline-N-oxide 
• 116529-85-2 2-methoxy-6-nitroquinoline 
• 59-31-4 2-quinolone 
• 59-31-4 2-hydroxyquinoline 
• 613-50-3 6-nitroquinoline 
• 22246-16-8 6-nitro-3,4-dihydro-1H-quinolin-2-one 
• 612-62-4 2-Chloroquinoline 
• 104-04-1 N-(4-Nitrophenyl)acetamide 
• 292638-85-8 acrylic acid methyl ester 
• 623-11-0 1-methyl-4-nitrosobenzene 
• 7664-93-9 sulfuric acid 
• 91538-60-2 N-(2-formyl-4-nitrophenyl)acetamide 

Downstream Products

• 29969-57-1 2-chloro-6-nitroquinoline 
• 79207-68-4 6-amino-2(1H)-quinolinone 
• 1616393-38-4 N-(3-((2-Oxo-6-(2H-tetrazol-5-yl)-1,2-dihydroquinolin-3-yl)amino)phenyl)pyrrolidine-1-carboxamide 
• 1616393-36-2 N-(3-((6-Ethoxy-2-oxo-1,2-dihydroquinolin-3-yl)amino)phenyl)pyrrolidine-1-carboxamide 
• 1616393-34-0 N-(3-((6-(3-Methoxyphenyl)-2-oxo-1,2-dihydroquinolin-3-yl)amino)phenyl)pyrrolidine-1-carboxamide 
• 1616393-32-8 N-(3-((6-cyano-2-oxo-1,2-dihydroquinolin-3-yl)amino)phenyl)pyrrolidine-1-carboxamide 
• 1616393-30-6 N-(3-((6-acetamido-2-oxo-1,2-dihydroquinolin-3-yl)amino)phenyl)pyrrolidine-1-carboxamide 
• 1616393-28-2 1-(2-Oxo-3-(phenylamino)-1,2-dihydroquinolin-6-yl)urea 
• 1616393-26-0 N-(3-(2-oxo-2-((2-(piperidin-1-yl)ethyl)amino)ethyl)-5-((2-oxo-6-ureido-1,2-dihydroquinolin-3-yl)amino)phenyl)pyrrolidine-1-carboxamide 
• 1616393-24-8 N-(3-((2-oxo-6-ureido-1,2-dihydroquinolin-3-yl)amino)phenyl)pyrrolidine-1-carboxamide 
• 1616393-22-6 N-(3-((1-(4-methoxybenzyl)-2-oxo-6-(2H-tetrazol-5-yl)-1,2-dihydroquinolin-3-yl)amino)phenyl)pyrrolidine-1-carboxamide 
• 1616393-20-4 N-(3-((6-ethoxy-1-(4-methoxybenzyl)-2-oxo-1,2-dihydroquinolin-3-yl)amino)phenyl)pyrrolidine-1-carboxamide 
• 1616393-18-0 N-(3-((1-(4-methoxybenzyl)-6-(3-methoxyphenyl)-2-oxo-1,2-dihydroquinolin-3-yl)amino)phenyl)pyrrolidine-1-carboxamide 
• 1616393-16-8 N-(3-((6-cyano-1-(4-methoxybenzyl)-2-oxo-1,2-dihydroquinolin-3-yl)amino)phenyl)pyrrolidine-1-carboxamide 

Relevant academic research and scientific papers

Efficient visible light mediated synthesis of quinolin-2(1H)-ones from quinolineN-oxides

Quinolin-2(1H)-ones are one of the important classes of compounds due to their prevalence in natural products and in pharmacologically useful compounds. Here we present an unconventional and hitherto unknown photocatalytic approach to their synthesis from easily available quinoline-N-oxides. This reagent free highly atom economical photocatalytic method, with low catalyst loading, high yield and no undesirable by-product, provides an efficient greener alternative to all conventional synthesis reported to date. The robustness of the methodology has been successfully demonstrated with easy scaling up to the gram scale.

N-(4-acetamidophenyl)-5-acetylfuran-2-carboxamide as a novel orally available diuretic that targets urea transporters with improved PD and PK properties

Urea transporters (UTs) have been identified as new targets for diuretics. Functional deletion of UTs led to urea-selective urinary concentrating defects with relative salt sparing. In our previous study, a UT inhibitor with a diarylamide scaffold, which is denoted as 11a, was demonstrated as the first orally available UT inhibitor. However, the oral bioavailability of 11a was only 4.38%, which obstructed its clinical application. In this work, by replacing the nitro group of 11a with an acetyl group, 25a was obtained. Compared with 11a, 25a showed a 10 times stronger inhibitory effect on UT-B (0.14 μM vs. 1.41 μM in rats, and 0.48 μM vs. 5.82 μM in mice) and a much higher inhibition rate on UT-A1. Moreover, the metabolic stability both in vitro and in vivo and the drug-like properties (permeability and solubility) of 25a were obviously improved compared with those of 11a. Moreover, the bioavailability of 25a was 15.18%, which was 3 times higher than that of 11a, thereby resulting in significant enhancement of the diuretic activities in rats and mice. 25a showed excellent potential for development as a promising clinical diuretic candidate for targeting UTs to treat diseases that require long-term usage of diuretics, such as hyponatremia.

BIFUNCTIONAL MOLECULES CONTAINING AN E3 UBIQUITINE LIGASE BINDING MOIETY LINKED TO A BCL6 TARGETING MOIETY

Bifunctional compounds, which find utility as modulators of B-cell lymphoma 6 protein (BCL6; target protein), are described herein. In particular, the bifunctional compounds of the present disclosure contain on one end a Von Hippel-Lindau, cereblon, Inhibitors of Apotosis Proteins or mouse double-minute homolog 2 ligand that binds to the respective E3 ubiquitin ligase and on the other end a moiety which binds the target protein, such that the target protein is placed in proximity to the ubiquitin ligase to effect degradation (and inhibition) of target protein. The bifunctional compounds of the present disclosure exhibit a broad range of pharmacological activities associated with degradation/inhibition of target protein. Diseases or disorders that result from aggregation or accumulation of the target protein are treated or prevented with compounds and compositions of the present disclosure.

Discovery of Benzopyridone-Based Transient Receptor Potential Vanilloid 1 Agonists and Antagonists and the Structural Elucidation of Their Activity Shift

Among a series of benzopyridone-based scaffolds investigated as human transient receptor potential vanilloid 1 (TRPV1) ligands, two isomeric benzopyridone scaffolds demonstrated a consistent and distinctive functional profile in which 2-oxo-1,2-dihydroquinolin-5-yl analogues (e.g., 2) displayed high affinity and potent antagonism, whereas 1-oxo-1,2-dihydroisoquinolin-5-yl analogues (e.g., 3) showed full agonism with high potency. Our computational models provide insight into the agonist-antagonist boundary of the analogues suggesting that the Arg557 residue in the S4-S5 linker might be important for sensing the agonist binding and transmitting signals. These results provide structural insights into the TRPV1 and the protein-ligand interactions at a molecular level.

SMALL MOLECULE INHIBITORS OF ACETYL COENZYME A SYNTHETASE SHORT CHAIN 2 (ACSS2)

The present invention relates to compounds of formula (I). The compounds may be used to modulate the acetyl coenzyme A synthetase short chain 2 (ACSS2) protein and may thereby treat, ameliorate or prevent a disease selected from cancer, bacterial infection, viral infection, parasitic infection, fungal infection, neurodegenerative disease, neurological disorder, cerebrovascular disease, cardiovascular disease, non- alcoholic fatty liver disease and obesity. Alternatively, or additionally, the compounds maybe used to promote healthy ageing.

METHODS OF CULTURING AND/OR EXPANDING STEM CELLS AND/OR LINEAGE COMMITTED PROGENITOR CELLS USING AMIDO COMPOUNDS

Provided are methods for expanding stem cells and/or lineage committed progenitor cells, such as hematopoietic stems cells and/or lineage committed progenitor cells, at least in part, by using compounds that antagonize AhR. The compounds are represented by formulae (I) (II) (III) (IV), wherein the letters and symbols a, b, c, d, e, f, g, Z, R1b, R2a and R2b have the meanings provided in the specification. Also provided are compositions comprising stem cells and/or lineage committed progenitor cells expanded by methods disclosed herein and methods for the treatment of diseases treatable by same.

Oxidative Aromatization of 3,4-Dihydroquinolin-2(1 H)-ones to Quinolin-2(1 H)-ones Using Transition-Metal-Activated Persulfate Salts

Inorganic persulfate salts were identified as efficient reagents for the oxidative aromatization of 3,4-dihydroquinolin-2(1H)-ones through the activation of readily available transition metals, such as iron and copper. The feasible protocol conforming to the requirement of green chemistry was utilized in the preparation of the key intermediate (7-(4-chlorobutoxy)quinolin-2(1H)-one 2) of brexpiprazole in 80% isolated yield on a 100 g scale, and different quinolin-2(1H)-one derivatives with various functional groups were demonstrated in 52-89% yields.

AMIDO COMPOUNDS AS AhR MODULATORS

Provided herein are compounds, compositions and methods of using the compounds and compositions for the treatment of diseases modulated, as least in part, by AhR. The compounds are represented by formulae Formula (I), (II), (III), (iv): wherein the letters and symbols a, b, c, d, e, f, g, Z, R1b, R2a and R2b have the meanings provided in the specification.

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.

Novel 8-nitroquinolin-2(1H)-ones as NTR-bioactivated antikinetoplastid molecules: Synthesis, electrochemical and SAR study

To study the antiparasitic 8-nitroquinolin-2(1H)-one pharmacophore, a series of 31 derivatives was synthesized in 1–5 steps and evaluated in vitro against both Leishmania infantum and Trypanosoma brucei brucei. In parallel, the reduction potential of all molecules was measured by cyclic voltammetry. Structure-activity relationships first indicated that antileishmanial activity depends on an intramolecular hydrogen bond (described by X-ray diffraction) between the lactam function and the nitro group, which is responsible for an important shift of the redox potential (+0.3 V in comparison with 8-nitroquinoline). With the assistance of computational chemistry, a set of derivatives presenting a large range of redox potentials (from ?1.1 to ?0.45 V) was designed and provided a list of suitable molecules to be synthesized and tested. This approach highlighted that, in this series, only substrates with a redox potential above ?0.6 V display activity toward L. infantum. Nevertheless, such relation between redox potentials and in vitro antiparasitic activities was not observed in T. b. brucei. Compound 22 is a new hit compound in the series, displaying both antileishmanial and antitrypanosomal activity along with a low cytotoxicity on the human HepG2 cell line. Compound 22 is selectively bioactivated by the type 1 nitroreductases (NTR1) of L. donovani and T. brucei brucei. Moreover, despite being mutagenic in the Ames test, as most of nitroaromatic derivatives, compound 22 was not genotoxic in the comet assay. Preliminary in vitro pharmacokinetic parameters were finally determined and pointed out a good in vitro microsomal stability (half-life > 40 min) and a 92% binding to human albumin.