1198-15-8

Usage

Classification

Organic compound
Belongs to the quinolone family.

Usage

Widely used in pharmaceutical and medicinal chemistry.

Biological activities

Antitumor properties.
Anti-inflammatory properties.
Anticonvulsant properties.

Enzyme inhibition

Inhibits lipoxygenase.
Involved in the production of leukotrienes, which are inflammatory mediators.

Chemical structure

Versatile building block.
Used for the synthesis of various drugs and bioactive compounds.

Importance

Important intermediate in the production of pharmaceuticals.
Potential applications in drug discovery and development.

Upstream product

• 94-34-8 N-(2-cyanoethyl)-N-methylaniline 
• 3334-56-3 N-methyl-N-(2-[hydroxycarbonyl]ethyl)aniline 
• 7446-70-0 aluminium trichloride 
• 1088708-44-4 3-[N-(2-iodophenyl)-N-methylamino]-N,N-dimethylpropanamide 
• 1088708-50-2 3-[N-(2-iodophenyl)-N-methylamino]-N-methoxy-N-methylpropanamide 
• 118670-86-3 N-(but-3-en-1-yl)-2-iodoaniline 
• 615-43-0 2-iodophenylamine 
• 57056-89-0 N-(but-3-en-1-yl)-2-iodo-N-methylaniline 
• 1407968-57-3 4-[N-(2-iodophenyl)-N-methylamino]butanol 
• 1407968-49-3 4-[N-(2-iodophenyl)-N-methylamino]butanal 
• 100-61-8 N-methylaniline 
• 2680-03-7 N,N-Dimethylacrylamide 
• 4295-36-7 2,3-dihydroquinolin-4(1H)-one 
• 74-88-4 methyl iodide 

Downstream Products

• 99057-84-8 6-bromo-1-methyl-2,3-dihydroquinolin-4-one 
• 121113-03-9 1,2,3,4-tetrahydro-1-methyl-4-oxoquinoline phenylhydrazone 
• 109094-25-9 3-(4-dimethylamino-benzylidene)-1-methyl-2,3-dihydro-1H-quinolin-4-one 
• 101782-93-8 3-(4-dimethylamino-anilino)-1-methyl-1H-quinolin-4-one 
• 3835-09-4 1-methyl-2,3-dihydro-1H-quinolin-4-one-(2,4-dinitro-phenylhydrazone) 
• 56857-96-6 1-methyl-3-phenylquinolin-4(1H)-one 
• 719-54-0 10-methyl-9, 10-dihydro-9-acridinone 
• 851390-46-0 1-methyl-1,2,3,4-tetrahydro-4-quinolinamine 
• 107520-34-3 6,8-dibromo-3-(4-dimethylamino-anilino)-1-methyl-1H-quinolin-4-one 
• 107621-79-4 6-bromo-3-(4-dimethylamino-anilino)-1-methyl-1H-quinolin-4-one 
• 108623-43-4 6-bromo-3-(4-dimethylamino-benzylidene)-1-methyl-2,3-dihydro-1H-quinolin-4-one 
• 83-54-5 1-methyl-4-quinolone 

Relevant academic research and scientific papers

Control over the chemoselectivity of Pd-catalyzed cyclization reactions of (2-iodoanilino)carbonyl compounds

The factors that control the chemoselectivity of palladium-catalyzed cyclization reactions of (2-iodoanilino)carbonyl compounds have been explored by an extensive experimental computational (DFT) study. It was found that the selectivity of the process, th

Selective C-H Olefination of Indolines (C5) and Tetrahydroquinolines (C6) by Pd/S,O-Ligand Catalysis

Herein, we report a highly selective C-H olefination of directing-group-free indolines (C5) and tetrahydroquinolines (C6) by Pd/S,O-ligand catalysis. In the presence of the S,O-ligand, a wide range of challenging indolines, tetrahydroquinolines, and olefins was efficiently olefinated under mild reaction conditions. The synthetic potential of this methodology was demonstrated by the efficient olefination of several indoline-based natural products.

PIPERIDINE DERIVATIVES AS HDAC1/2 INHIBITORS

Provided herein are compounds, pharmaceutical compositions comprising such compounds, and methods of using such compounds to treat diseases or disorders associated with HDACl and/or HDAC2 activity.

SPIROCYCLIC HAT INHIBITORS AND METHODS FOR THEIR USE

Compounds having a structure of Formula (IX) or a stereoisomer, tautomer or pharmaceutically acceptable salt thereof, wherein R1, R2a, R2b, R3a, R3b, R4a, R4b, Q1----Q2, R6, R7, A, B, W, x, and y are as defined herein and are provided. Pharmaceutical compositions comprising such compounds and methods for treating various HAT-related conditions or diseases, including cancer, by administration of such compounds are also provided.

Formation of acridones by ethylene extrusion in the reaction of arynes with β-lactams and dihydroquinolinones

N-Unsubstituted β-lactams react with a molecule of aryne by insertion into the amide bond to form a 2,3-dihydroquinolin-4-one, which subsequently reacts with another molecule of aryne to form an acridone by extrusion of a molecule of ethylene. 2,3-Dihydroquinolin-4-ones react under the same reaction conditions to afford identical results. This is the first example of ethylene extrusion in aryne chemistry.

Intramolecular Pd(0)-catalyzed reactions of (2-iodoanilino)-aldehydes: A joint experimental-computational study

An extensive joint experimental-computational density functional theory (DFT) study has been carried out to gain insight into the factors that control the chemoselectivity (i.e., acylation vs α-arylation reaction) of palladium-catalyzed cyclizations of (2-iodoanilino)-aldehydes. To this end, the nature of the tethers joining the aniline nitrogen and the aldehyde moiety, different palladium precatalysts and reaction conditions (base and temperature), as well as different additives (mono- and bidendate ligands) has been explored. The adequate selection of these variables allows for the control of the selectivity of the process. Thus, (2-iodoanilino)-aldehydes generally lead to the formation of nucleophilic addition derived products when Cs 2CO3/Et3N is used as base. In contrast, the use of stronger bases like KtOBu (in the presence of PhOH) mainly forms α-arylation reaction products. The different reaction pathways leading to the experimentally observed reaction products have been studied by means of computational tools.

Intramolecular Pd(0)-catalyzed reactions of β-(2-iodoanilino) carboxamides: Enolate arylation and nucleophilic substitution at the carboxamide group

(Chemical Equation Presented) Two different reaction pathways, the enolate arylation and the acylation of the aryl halide, can be promoted by a Pd(0) catalyst starting from β-(2-iodoanilino) carboxamides. The intramolecular acylation of β-(2-iodoanilino) carboxamides reported here is the first example of a nucleophilic attack of a σ-arylpalladium species at the carboxamide group, a framework that is usually inert toward organopalladium reagents.

ANTAGONISTS OF THE TRPV1 RECEPTOR AND USES THEREOF

The present application is directed to compounds that are TRPV1 antagonists and have formula (I) wherein variables Ar1, L1, R1, R2, R3, R4, R5, Y1, Y2, and Y3, are as defined in the description, which are useful for treating disorders caused by or exacerbated by vanilloid receptor activity.

USE OF 2-IMIDAZOLES FOR THE TREATMENT OF CNS DISORDERS

The present invention relates to the use of compounds of formula (I) R1 is hydrogen, tritium, hydroxy, lower alkyl, lower alkoxy, halogen, nitro, amino or lower alkyl substituted by halogen; R2 is hydrogen, hydroxy or lower alkyl; X is N and Y is CH or CH2 or CH-lower alkyl or X is CH and Y is N; Q is CH2, O, NH, N-alkyl or N-SO2-alkyl or N-SO2-toluen-4-yl; W is CH2 or a bond are independently from one another 1, 2 or 3; when m is 2 or 3, R2 may m, n be the same or not; when n is 2 or 3, R1 may be the same or not; the dotted lines may each be independently from one another a bond or not; and to their pharmaceutically active salts, racemic mixtures, enantiomers, optical isomers and tautomeric forms of compounds of formula (I) for the preparation of medicaments for the treatment of depression, anxiety disorders, bipolar disorder, attention deficit hyperactivity disorder, stress-related disorders, psychotic disorders such as schizophrenia, neurological diseases such as Parkinson's disease, neurodegenerative disorders such as Alzheimer's disease, epilepsy, migraine, hypertension, substance abuse and metabolic disorders such as eating disorders, diabetes, diabetic complications, obesity, dyslipidemia, disorders of energy consumption and assimilation, disorders and malfunction of body temperature homeostasis, disorders of sleep and circadian rhythm, and cardiovascular disorders.

New approach to the synthesis of 1,2,3,4-tetrahydroquinolin-4-ones

The reaction of aromatic amines with complexes of N,N-dimethylacrylamide and N,N-dimethylmethacrylamide with trifluoromethanesulfonic anhydride leads to the formation of tetrahydro-4-quinolones and 3-methyltetrahydro-4-quinolones respectively. 1997 Plenum Publishing Corporation.