20877-86-5

Usage

Type

Synthetic chemical compound

Category

Organic

Common uses

Dye and pigment
Manufacturing of plastics
Inks and coatings
Textile industry (coloring fabrics)

Physical properties

Orange color
Belongs to the oxazine family

Potential health effects

Skin irritation, respiratory issues
May have harmful effects on aquatic organisms

Safety measures and precautions

Proper handling and disposal required to minimize risks

Upstream product

• 91-40-7 2-(phenylamino)benzoic acid 
• 541-41-3 chloroformic acid ethyl ester 
• 75-44-5 phosgene 
• 16463-38-0 potassium 2-chlorobenzoate 
• 62-53-3 aniline 
• 35708-19-1 Methyl N-phenylanthranilate 
• 503-38-8 trichloromethyl chloroformate 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 108-86-1 bromobenzene 
• 118-48-9 isatoic anhydride 
• 603-33-8 triphenylbismuthane 
• 723-89-7 1-phenyl-indole-2,3-dione 
• 91-56-5 indole-2,3-dione 

Downstream Products

• 56043-02-8 N-Phenyl-trithioisatosaeureanhydrid 
• 1211-19-4 2-phenylaminobenzamide 
• 54675-12-6 4-hydroxy-3-nitro-1-phenyl-2(1H)-quinolone 
• 93595-31-4 C₁₆H₁₈N₄O₂ 
• 115869-40-4 (4-Oxo-1-phenyl-1,4-dihydro-quinolin-2-ylmethyl)-phosphonic acid dimethyl ester 
• 91-40-7 2-(phenylamino)benzoic acid 
• 115869-41-5 (3-Methyl-4-oxo-1-phenyl-1,4-dihydro-quinolin-2-ylmethyl)-phosphonic acid dimethyl ester 
• 115869-42-6 (3-Isopropyl-4-oxo-1-phenyl-1,4-dihydro-quinolin-2-ylmethyl)-phosphonic acid dimethyl ester 
• 4323-59-5 1-phenyl-3H-1(H),4(H)-benzodiazepin-2,5-dione 
• 73480-65-6 N-(3-Hydroxy-propyl)-2-phenylamino-benzamide 
• 53044-24-9 N-Phenyl-o-(hydroxymethyl)aniline 
• 110254-64-3 4-chloro-3-nitro-1-phenyl-2(1H)-quinolone 
• 141945-49-5 4-amino-3-nitro-1-phenylquinolin-2(1H)-one 
• 1027276-46-5 3,4-Diamino-1-phenyl-1H-quinolin-2-one 

Relevant academic research and scientific papers

Synthesis of Ring-Fused, N-Substituted 4-Quinolinones Using p Ka-Guided, Base-Promoted Annulations with Isatoic Anhydrides: Total Synthesis of Penicinotam

An anionic annulation strategy employing isatoic anhydrides and a wide assortment of enolizable partners was developed to afford over 80 novel ring-fused, N-substituted 4-quinolinones, an underrepresented privileged template. Multiple factors governing the efficiency of the transformation were determined, resulting in a reliable and tunable synthetic platform applicable for a broad range of substrates with variable deprotonation susceptibility, such as tetramic and tetronic acids, cyclic 1,3-diketones, and cycloalkanones. Application to the synthesis of bioactive, pyrrolizine-fused 4-quinolinone, penicinotam 3, resulted in the most brief and highest yielding total synthesis of the alkaloid in three steps and a 36% overall yield.

Synthesis, biological screening, and molecular docking of quinazolinone and quinazolinethione as phosphodiesterase 7 inhibitors

N-Substituted isatoic anhydrides were used as starting materials for the synthesis of compounds 5–16 through alkali hydrolysis, Schiff base reactions, and oxidation. Compounds 18–23 were obtained by thionation of their oxo isosteres using Lawesson's reage

Synthesis of methyl 2-[(1,2-dihydro-4-hydroxy-2-oxo-1-phenylquinolin-3-yl) carbonylamino] alkanoates and methyl 2-[2-((1,2-dihydro-4-hydroxy-2-oxo-1-phenylquinolin-3-yl)carbonyl-amino)alkanamido] alkanoate

A series of methyl 2-[(1,2-dihydro-4-hydroxy-2-oxo-1-phenylquinolin-3-yl)carbonylamino] alkanoates 7a-f has been developed by the direct condensation of ethyl [4-hydroxy-2-oxo-1-phenyl-1,2-dihydro-3-quinoline] carboxylate 4 with amino acid ester hydrochloride in the presence of triethylamine. The quinoline amino acid esters 7a-f were the key intermediate for the preparation of a series of methyl 2-[2-((1,2-dihydro-4-hydroxy-2-oxo-1-phenylquinolin-3-yl)carbonylamino)alkanamido] alkanoate 10-13(a-f) via azide coupling method with amino acid ester. {figure presented}.

Synthesis and antiproliferative activity of 6,7-disubstituted-4-phenoxyquinoline derivatives bearing the 2-oxo-4-chloro-1,2-dihydroquinoline-3-carboxamide moiety

A series of 6,7-disubstituted-4-phenoxyquinoline derivatives bearing the 2-oxo-4-chloro-1,2-dihydroquinoline-3-carboxamide moiety were synthesized, and evaluated for their antiproliferative activity against 5 cancer cell lines (H460, HT-29, MKN-45, A549, and U87MG). Most compounds showed moderate to excellent potency, and compared to foretinib, the most promising analog 42 (c-Met/Flt-3 IC50= 1.21/2.15 nM) showed a 6.1-fold increase in activity against H460 cell line in vitro. The enzymatic assays (c-Met, VEGFR-2, Flt-3, PDGFR-β, c-Kit, and EGFR) of compound 42 were evaluated in vitro. Docking analysis showed that compound 42 could form three hydrogen bonds with c-Met. Structure–activity relationship studies indicated that a more water-soluble cyclic tertiary amine and electron-withdrawing groups at 4-position of the phenyl ring contribute to the antitumour activity.

Isatoic anhydride and its process for synthesis of derivatives of

The invention discloses a synthesis method of isatoic anhydride and a derivative thereof, relating to the technical field of chemical synthesis. In the presence of catalysis of an organic selenium catalyst, isatin or a derivative thereof is oxidized by using hydrogen peroxide to prepare the isatoic anhydride and the derivative thereof. The synthesis method disclosed by the invention is simple and easily available in raw materials, low in cost, clean in oxidizing agent, free from a metal catalyst, and environmentally friendly, can be carried out in a neutral environment, and is small in corrosion to equipment.

1,3-dipolar cycloaddition-decarboxylation reactions of an azomethine ylide with isatoic anhydrides: Formation of novel benzodiazepinones

A nonstabilized azomethine ylide reacts with a wide range of substituted isatoic anhydrides to afford novel 1,3-benzodiazepin-5-one derivatives, which are generally isolated in high yield. The transformations involve 1,3-dipolar cycloaddition reactions of the ylide with the anhydrides to give transient, and in a representative case spectroscopically observable, oxazolidine intermediates that undergo ring-opening-decarboxylation-ringclosing reaction cascades to yield the 1,3-benzodiazepin-5-one products.

TUMOR NECROSIS FACTOR ALPHA INHIBITORS AND THEIR USE IN THE TREATMENT OF HUMAN DISEASES

treatment of a variety of disorders, including the treatment of pathological conditions associated with tumor necrosis factor alpha. The inhibitors of tumor necrosis factor alpha have the following structures: including stereoisomers, pharmaceutically acceptable salts, and solvates thereof, wherein substituents are as defined herein. Compositions containing an inhibitor of tumor necrosis factor alpha in combination with a pharmaceutically acceptable carrier are also provided, as well as methods for use of the same.

3-(1,1-dioxo-2H-(1,2,4)-benzothiadiazin-3-yl)-4-hydroxy-2(1H)-quinolinones, potent inhibitors of hepatitis C virus RNA-dependent RNA polymerase

Recently, we disclosed a new class of HCV polymerase inhibitors discovered through high-throughput screening (HTS) of the GlaxoSmithKline proprietary compound collection. This interesting class of 3-(1,1-dioxo-2H-1,2,4- benzothiadiazin-3-yl)-4-hydroxy-2(1H)-quinolinones potently inhibits HCV polymerase enzymatic activity and inhibits the ability of the subgenomic HCV replicon to replicate in Huh-7 cells. This report will focus on the structure-activity relationships (SAR) of substituents on the quinolinone ring, culminating in the discovery of 1-(2-cyclopropylethyl)-3-(1,1-dioxo-2H-1,2,4- benzothiadiazin-3-yl)-6-fluoro-4-hydroxy-2(1H)-quinolinone (130), an inhibitor with excellent potency in biochemical and cellular assays possessing attractive molecular properties for advancement as a clinical candidate. The potential for development and safety assessment profile of compound 130 will also be discussed.

Synthesis and Biological Evaluation of New 1,2-Dihydro-4-hydroxy-2-oxo-3-quinolinecarboxamides for Treatment of Autoimmune Disorders: Structure-Activity Relationship

Roquinimex-related 3-quinolinecarboxamide derivatives were prepared and evaluated for treatment of autoimmune disorders. The compounds were tested in mice for their inhibitory effects on disease development in the acute experimental autoimmune encephalomyelitis model and selected compounds in the beagle dog for induction of proinflammatory reaction. Structure-activity relationships are discussed. Compound 8c, laquinimod, showed improved potency and superior toxicological profile compared to the lead compound roquinimex (1b, Linomide) and was selected for clinical studies (currently in phase II).

Promotion of reaction of N-H bonds with triarylbismuth and cupric acetate

Arylation of a diverse group of N-H containing compounds at room temperature with triarylbismuth and cupric acetate in the presence of a tertiary amine promoter, such as triethylamine or pyridine, is described. This mild and highly efficient procedure, which is based on Barton's earlier work on the arylation of amines, can be applied to amides, imides, ureas, carbamates, and sulfonamides. Copyright (C) 1996 Elsevier Science Ltd.