54802-19-6

Usage

Uses

Used in Pharmaceutical Industry:
5,6,7,8-TETRAHYDRO-2(1H)-QUINOLINONE is used as a synthetic intermediate for the development of pharmaceutical products. Its unique structure and properties make it a valuable component in the synthesis of various drugs, contributing to the advancement of medicine and healthcare.

InChI:InChI=1/C9H11NO/c11-9-6-5-7-3-1-2-4-8(7)10-9/h5-6H,1-4H2,(H,10,11)

Upstream product

• 769092-24-2 2-[(dimethylamino)methyl]cyclohexanone 
• 41220-29-5 N-carbamoylmethylpyridinium chloride 
• 16326-65-1 5,6,7,8-tetrahydrocoumarin 
• 1199941-94-0 C₁₁H₁₅NO₄ 
• 4594-78-9 cyclohexanone-2-propionitrile 
• 3056-73-3 N-phenylcinnamamide 
• 4241-13-8 2-oxo-1,2,5,6,7,8-hexahydro-3-quinoline-3-carbonitrile 
• 59-31-4 2-hydroxyquinoline 
• 108-94-1 cyclohexanone 
• 922-67-8 propynoic acid methyl ester 

Downstream Products

• 10333-11-6 3,4,5,6,7,8-hexahydro-2-quinolinone 
• 80818-55-9 3,5,6,7,8,8a-hexahydroquinolin-2(1H)-one 
• 54968-03-5 3-bromo-5,6,7,8-tetrahydro-2(1H)-quinolone 
• 71308-91-3 2-bromo-5,6,7,8-tetrahydroquinoline 
• 858341-80-7 N-[4-(3,5-dimethyl-benzyl)-2-methoxy-5,6,7,8-tetrahydro-quinolin-3-yl]-2,2-dimethyl-propionamide 
• 858342-91-3 N-[2-methoxy-4-(3-methyl-benzoyl)-5,6,7,8-tetrahydro-quinolin-3-yl]-2,2-dimethyl-propionamide 
• 858342-41-3 N-[4-(hydroxy-m-tolyl-methyl)-2-methoxy-5,6,7,8-tetrahydro-quinolin-3-yl]-2,2-dimethyl-propionamide 
• 858343-00-7 3-amino-4-(3-methyl-benzoyl)-5,6,7,8-tetrahydro-1H-quinolin-2-one 
• 248248-64-8 3-amino-4-(3,5-dimethyl-benzyl)-5,6,7,8-tetrahydro-1H-quinolin-2-one 
• 129337-86-6 2-chloro-5,6,7,8-tetrahydroquinolin-8-one 
• 130861-73-3 2-chloro-8-hydroxy-5,6,7,8-tetrahydroquinoline 
• 91-22-5 quinoline 

Relevant academic research and scientific papers

Method for preparing chiral nitrogen-phosphorus ligand L-8 containing pyridocyclopentane

The invention discloses a method for preparing chiral nitrogen-phosphorus ligand L-8 containing pyridocyclopentane, and belongs to the technical field of medical intermediate chiral ligands. The chiral nitrogen-phosphorus L-8 ligand is prepared from cyclopentanone through the steps of addition, cyclization, chlorination, asymmetric boronation, oxidation, coupling, esterification and the like in sequence, large-scale preparation is relatively easy to achieve through the route, and the defect that in a traditional route, the yield is low in the first step of ring closing reaction and chiral alcohol preparation is overcome, and by selecting a proper chiral ligand, and combining with butyl lithium, asymmetric synthesis of chiral alcohol is realized, and a chiral separation column mode adoptedin literature is avoided.

Method for synthesizing chiral nitrogen-phosphorus ligand L-8 containing pyridocycloheptane

The invention discloses a method for synthesizing a chiral nitrogen-phosphorus ligand L-8 containing pyridocycloheptane, and belongs to the technical field of medical intermediate chiral ligands. Thechiral nitrogen-phosphorus L-8 ligand is prepared from cyclopentanone through the steps of addition, cyclization, chlorination, asymmetric boronation, oxidation, coupling, esterification and the likein sequence, large-scale preparation is relatively easy to achieve through the route, and the defect that in a traditional route, the yield is low in the first step of ring closing reaction and chiralalcohol preparation, and by selecting a proper chiral ligand, and combining with butyl lithium, asymmetric synthesis of chiral alcohol is realized, and a chiral separation column mode adopted in literature is avoided.

FLUORSCENT DYES WITH LARGE STOKES SHIFTS

Herein are disclosed fluorescent dyes based around a framework for a ligand comprising a pyridyl group linked to a diaryl anilido unit. A variety of ligands based on this framework are disclosed. The ligands chelate to a BF2 center to produce the fluorescent dye. The disclosed dyes combine longer Stokes shifts (approximately 100 nm) with increased quantum yields. They are also photostable in aqueous and organic solutions for several hours. These dyes may be used in the labeling of biomolecules for bioimaging and assays. Also disclosed are methods for the synthesis of these dyes.

Construction of 5,6-ring-fused 2-pyridones: An effective annulation tactic achieved in water

An efficient protocol to annulate the 5,6-fused 2-pyridone ring system, exploiting a tandem condensation of propiol-amide and cyclic -keto methyl esters in water, followed by acid- or base-promoted intramolecular ring closure and decarboxylation, has been

Tetrahydroquinilinones, tetrahydronaphthyridones and derivatives thereof

Tetrahydroquinolinone and tetrahydronaphthyridone cannabinoid receptor ligand compounds and stereoisomers, mixtures of stereoisomers, prodrugs, pharmaceutically acceptable salts, hydrates, solvates, acid salt hydrates, and isomorphic crystalline forms the

PYRIDINE DERIVATIVES AND THEIR USE AS MEDICAMENTS FOR TREATING DISEASES RELATED TO MCH RECEPTOR

The present invention encompasses novel substituted pyridine compounds of Formula (I), which act as MCH receptor antagonists. These compositions and pharmaceutical compositions thereof are useful in the prophylaxis or treatment of improving memory function, sleeping and arousal, anxiety, depression, mood disorders, seizure, obesity, diabetes, appetite and eating disorders, cardiovascular disease, hypertension, dyslipidemia, myocardial infarction, binge eating disorders including bulimia, anorexia, mental disorders including manic depression, schizophrenia, delirium, dementia, stress, cognitive disorders, attention deficit disorder, substance abuse disorders and dyskinesias including Parkinson's disease, epilepsy, and addiction.

4-Benzyl and 4-benzoyl-3-dimethylaminopyridin-2(1H)-ones: In vitro evaluation of new C-3-amino-substituted and C-5,6-alkyl-substituted analogues against clinically important HIV mutant strains

In a program to optimize the anti-HIV activity of the 4-benzyl and 4-benzoyl-3-dimethylaminopyridinones 9 and 10, lead compounds in a new class of highly potent non-nucleoside type inhibitors of HIV-1 reverse transcriptase, modification of the alkyl substitutents at the C-5 and C-6 positions on the pyridinone ring and of the substitutents on the C-3 amino group has been studied. Of the 17 new 5/6-modified analogues prepared, compounds 31b and 32b substituted at C-5 by an extended nonpolar chain containing an ether function and a C-6 methyl group and compound 35 bearing a C-5 ethyl/C-6 hydroxymethyl substituent pattern were selected on the basis of their in vitro activity against wild-type HIV and the three principle mutant strains, K103N, Y181C, and Y188L. When tested further, it was shown that these molecules, and in particular compound 35, are globally more active than 9, 10, and efavirenz against an additional eight single [L100I, K101E, V106A, E138K, V179E, G190A/S, and F227C] and four double HIV mutant strains [L100I + K103N, K101E + K103N, K103N + Y181C, and F227L + V106A], which are clinically relevant. Concerning modulation of the N-3 substituent, 36 new analogues were prepared. Of these, the N-methyl-N-(2-methoxyethyl)-substituted compounds 40, 42, and 62, as well as the doubly modified compounds 77a and 77b, were selected from the initial screen and were subsequently shown to be active at sub-micromolar concentrations (IC50's) against all the other mutant strains except K103N + Y181C and F227L + V106A. Two possible, but distinct, modes of binding of these analogues in RT were suggested from molecular modeling studies. The preferred mode of binding for compound 62, corresponding to the predicted "orientation 1", was revealed in the X-ray crystal structure of the compound 62-RT complex.

Reactions of 2-, 3- and 4-quinolinols with cyclohexane and benzene in superacids

Isomeric 2-, 3- and 4-quinolinols (11-13) underwent selective ionic hydrogenation with cyclohexane in CF3SO3H-SbF5 system to give 5,6,7,8-tetrahydro-2(1H)-quinolinone, 5,6,7,8-tetrahydro-3-quinolinol and 5,6,7,8-tetrahydro-4(1H)-quinolinone (28-30), respectively. When reaction was carried out in the presence of excess of aluminum chloride, 11 gave 3,4-dihydro-2(1H)-quinolinone (31), whereas 13 gave the product (30). Compounds (11) and (13) condense with benzene in the presence of aluminum halides producing phenyl substituted derivatives of 28, 31 and 30 (products 32-34), respectively. The mechanism of these and related reactions involving superelectrophilic dicationic intermediates is discussed.

Novel potent and selective central 5-HT3 receptor ligands provided with different intrinsic efficacy. 1. Mapping the central 5-HT3 receptor binding site by arylpiperazine derivatives

Synthesis and pharmacological evaluation of a series of condensed quinoline and pyridine derivatives bearing a N-methylpiperazine moiety attached to the 2-position of the quinoline or pyridine nucleus are described. 5-HT receptor binding studies revealed subnanomolar affinity for the 5-HT3 receptor subtype in some of the compounds under study. The most active compound (5b) displayed a K(i) value about 1 order of magnitude higher than that of quipazine along with a higher selectivity. The potential 5-HT3 agonist/antagonist activity of four selected compounds was assessed in vitro on 5-HT3 receptor-dependent [14C]guanidinium uptake in NG 108-15 cells. Compound 5j acted as a 5-HT3 agonist in this assay with an EC50 value close to that reported for quipazine, while 5b was a partial agonist with an EC50 value of about 0.25 nM, and compound 5c possessed antagonist properties with an IC50 value (?8 nM) in the same range as those of previously characterized 5-HT3 receptor antagonists. Qualitative and quantitative structure-affinity relationship studies carried out by making use of theoretical molecular descriptors allowed to elucidate the role of the main pharmacophoric components and to develop a model for the interaction of the 5-HT3 ligands related to quipazine with their receptor.