54197-66-9

Usage

Chemical Properties

Off-white solid

Uses

A metabolite of Cilostazole.

InChI:InChI=1/C9H9NO2/c11-7-2-3-8-6(5-7)1-4-9(12)10-8/h2-3,5,11H,1,4H2,(H,10,12)

Upstream product

• 19314-10-4 3-chloro-propionic acid-(4-hydroxy-anilide) 
• 19314-15-9 3-chloro-propionic acid p-phenetidide 
• 91523-37-4 N-methoxy-3,4-dihydro-1H-quinolin-2-one 
• 19313-87-2 N-(4-methoxyphenyl)-β-chloropropanamide 
• 553-03-7 3,4-dihydro-2(1H)-quinolone 
• 123-30-8 4-amino-phenol 
• 625-36-5 2-chloropropionyl chloride 
• 7446-70-0 aluminium trichloride 
• 77248-69-2 C₉H₇NO₅ 
• 635-46-1 1,2,3,4-tetrahydroisoquinoline 
• 3460-04-6 3-chloro-N-phenylpropionamide 
• 62-53-3 aniline 
• 22246-13-5 6-amino-3,4-dihydro-1H-quinolin-2-one 
• 104-94-9 4-methoxy-aniline 

Downstream Products

• 73963-70-9 6-[3-(1-Phenyltetrazol-5-yl)propoxy]-3,4-dihydrocarbostyril 
• 78876-16-1 6-<3-(1-cyclohexyl-5-tetrazolyl)propoxy>-2-oxo-1,2,3,4-tetrahydroquinoline 
• 73963-71-0 6-[3-(1-Cyclohexylmethyltetrazol-5-yl)propoxy]-3,4-dihydrocarbostyril 
• 86843-26-7 6-[5-(1-Cyclohexyl-1H-tetrazol-5-yl)-pentyloxy]-3,4-dihydro-1H-quinolin-2-one 
• 78876-17-2 6-[4-(1-Cyclohexylmethyl-1H-tetrazol-5-yl)-butoxy]-3,4-dihydro-1H-quinolin-2-one 
• 86843-27-8 6-{4-[1-(2-Cyclohexyl-ethyl)-1H-tetrazol-5-yl]-butoxy}-3,4-dihydro-1H-quinolin-2-one 
• 73963-69-6 6-[3-(1-Benzyltetrazol-5-yl)propoxy]-3,4-dihydrocarbostyril 
• 73963-72-1 6-[4-(1-cyclohexyl-1H-tetrazol-5-yl)butoxy]-3,4-dihydrocarbostyril 
• 87153-00-2 6-{4-[1-((1R,3S)-3-Benzyloxy-cyclohexyl)-1H-tetrazol-5-yl]-butoxy}-3,4-dihydro-1H-quinolin-2-one 
• 87153-00-2 6-{4-[1-((1R,3R)-3-Benzyloxy-cyclohexyl)-1H-tetrazol-5-yl]-butoxy}-3,4-dihydro-1H-quinolin-2-one 
• 87152-97-4 6-(4-<1-(trans-4-benzyloxycyclohexyl)-1H-5-tetrazolyl>butoxy)-2-oxo-1,2,3,4-tetrahydroquinoline 
• 87152-98-5 6-{4-[1-((1R,2S)-2-Benzyloxy-cyclohexyl)-1H-tetrazol-5-yl]-butoxy}-3,4-dihydro-1H-quinolin-2-one 
• 87152-98-5 6-{4-[1-((1R,2R)-2-Benzyloxy-cyclohexyl)-1H-tetrazol-5-yl]-butoxy}-3,4-dihydro-1H-quinolin-2-one 
• 54197-64-7 6-methoxy-2-oxo-1,2,3,4-tetrahydroquinoline 

Relevant academic research and scientific papers

Preparation method 6 -hydroxy -3-4 - dihydro -2 (1H)-quinolone (by machine translation)

HCl is added to the reaction solvent N, N - dimethylacetamide, HCl is added, solid matter is precipitated, filtered 2, the filter cake is washed 6 - times with ethanol, and then the 6 - residual solvent residue is 1 - 3 hours removed by -3 drying to 4 - obtain -2 the final product -3 hydroxyl 4 - 3 -2 dihydro 4 - 3 - (1H)-quinolonecarboxylic acid, N, N-(4 - 20 - 30 °C methoxyphenyl 0.05 - 0.2) propionamide. 1 is added 1H to the reaction solvent N, N-dimethylacetamide, and then the solvent is evaporated. The ionic liquid catalyst is high in thermal stability and catalytic performance, high in product yield, simple in reaction steps, easy to control and suitable for industrial production characteristics. (by machine translation)

Multi-Functional Oxidase Activity of CYP102A1 (P450BM3) in the Oxidation of Quinolines and Tetrahydroquinolines

Tetrahydroquinoline, quinoline, and dihydroquinolinone are common core motifs in drug molecules. Screening of a 48-variant library of the cytochrome P450 enzyme CYP102A1 (P450BM3), followed by targeted mutagenesis based on mutation-selectivity correlations from initial hits, has enabled the hydroxylation of substituted tetrahydroquinolines, quinolines, and 3,4-dihydro-2-quinolinones at most positions around the two rings in good to high yields at synthetically relevant scales (1.5 g L?1 day?1). Other oxidase activities, such as C?C bond desaturation, aromatization, and C?C bond formation, were also observed. The enzyme variants, with mutations at the key active site residues S72, A82, F87, I263, E267, A328, and A330, provide direct and sustainable routes to oxy-functionalized derivatives of these building block molecules for synthesis and drug discovery.

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.

Synthesis method of 6-hydroxyl-3,4-dihydro-2(1H)-quinolinone

The invention provides a synthesis method of 6-hydroxyl-3,4-dihydro-2(1H)-quinolinone. The synthesis method comprises the following steps: 1) taking p-alkoxyaniline as a raw material to react with 3-chloro-propionyl chloride, so as to prepare N-(4-alkoxyphenyl)-3-chloropropene amide; 2) dissolving the N-(4-alkoxyphenyl)-3-chloropropene amide obtained by step 2) into an organic solvent and adding acatalyst palladium chloride; raising the temperature to 100 to 110 DEG C under the pressure of 3 to 5kg, and carrying out heat preservation and reaction for 3 to 4h; after cooling to room temperature, filtering; spinning and drying filtrate to remove the organic solvent, so as to obtain a 6-hydroxyl-3,4-dihydro-2(1H)-quinolinone crude product; 3) recrystallizing the 6-hydroxyl-3,4-dihydro-2(1H)-quinolinone crude product obtained by step 3), de-coloring and filtering to obtain an off-white color solid 6-hydroxyl-3,4-dihydro-2(1H)-quinolinone. The synthesis method has the advantages of simplicity in operation, high yield and lower cost.

Preparation method of cilostazol

The invention discloses a preparation method of cilostazol and belongs to the field of medicines. The preparation method comprises the following steps: firstly, reacting 4-methoxyaniline with 3-chloropropionyl chloride in the presence of a solvent or no solvent; after a TLC (thin layer chromatography) detecting reaction is finished, adding aluminum trichloride into a system, and carrying out temperature raising reaction for 1 to 16 hours to obtain 6-hydroxy-3,4-dihydroquinoline-2-keto; secondly, in the presence of alkali, carrying out heating reaction on the 6-hydroxy-3,4-dihydroquinoline-2-keto obtained in the first step and 5-(4-chlorobutyl)-1-cyclohexanyl tetrazole in normal propyl alcohol to obtain the cilostazol. The high-purity cilostazol can be obtained by adopting the method disclosed by the invention; the preparation method has the advantages of few steps of the whole synthetic route, high yield, low cost, less wastewater and suitability for industrial production.

Synthesis of novel 3,4-dihydroquinolin-2(1H)-one guanidines as potential antihypertensive agents

Hydroxy-3,4-dihydroquinolin-2(1H)-ones (4a-c) were synthesized by intramolecular Friedel Craft alkylation of N-(methoxyphenyl)-3- chloropropionamides (3a-c), obtained by acylation of anisidine with chloropropionyl chloride. The hydroxy-3,4-dihydro quinolin-2(1H)- ones (4a-c) were treated with various dibromo alkanes under phase transfer catalyst conditions at room temperature to give bromoalkyloxy- 3,4-dihydroquinolin-2(1H)- ones (5a-l) which on further reaction with guanidine hydrochloride in dimethyl formamide afforded N-{4- [(2-oxo-1,2,3,4-tetrahydroquinolin-5-yl)oxy]alkyl} guanidines (6a-l). These compounds were synthesized as potential antihypertensive agents.

Synthesis of related substances of cilostazol

The impurities in API of cilostazol were detected by LC/MS during the process development. The structures of two impurities 6 and 7 and the related formation mechanisms were proposed. Synthesis of 6 and 7 was conducted for confirmation of the speculated structures.

Synthesis of indolones and quinolones by reductive cyclisation of o-nitroaryl acids using zinc dust and ammonium formate

A novel protocol for the synthesis of indolone and quinolone derivatives from o-nitroaryl acids was developed using Zn and HCO2NH4 under supercritical fluid carbon dioxide (scCO2) medium. The process involves the reduction of the nitro group to an amino group followed by in situ cyclisation.

Synthesis and anticonvulsant activity of 1-substituted-7-benzyloxy-4,5- dihydro-[1,2,4]triazolo[4,3-a]quinoline

Starting from 6-hydroxy-3,4-dihydro-1H-quinoline-2-one, a series of 1-substituted-7-benzyloxy-4,5-dihydro-[1,2,4]triazolo[4,3-a]quinolines was synthesized and their structures were characterized using IR, 1H-NMR, MS, and elemental analysis techniques. Anticonvulsant activity was evaluated in the maximal electroshock (MES) test, subcutaneous pentylenetetrazol (scMet) test, and rotarod neurotoxicity test. The most active compound was 7-benzyloxy-4,5-dihydro-[1,2,4]triazolo[4,3-a]quinoline 4a. Its ED50 in the MES and scMet tests was 17.3 and 24mg·kg-1, respectively. The safest compound was 4g, 1-phenyl-7-benzyloxy-4,5-dihydro-[1,2, 4]triazolo[4,3-a]quinoline, with TD50 and protective index (PI) (PI=TD50/ED50) values of greater than 300mg·kg -1 and 13, respectively. The PI value of compound 4g was better than that of most marketed drugs. Structure-activity relationships are also described in this paper.

SUBSTITUTED BENZOLACTAM COMPOUNDS

This invention relates to compounds of general formula (I): or a pharmaceutically acceptable salt thereof, W, T, Y, X, Q, R, R, and R are defined herein. This invention also relates to compounds of formula (I), depicted above, wherein Y is -NH-; T is (2S,3S)-2-phenylpiperidin-3-yl, where the phenyl group of said (2S, 3S)-2-phenylpiperidine-3-yl may optionally be substituted with fluoro; Q is oxygen and is double bonded to the carbon atom to which it is attached, X is methoxy or ethoxy, R is hydrogen, methyl or halo-C1-C2 alkyl, W is methylene, ethylene or vinylene; R and R are independently hydrogen or methyl, or one of R or R may be hydroxy, when W is ethylene, R and R are both methyl, when W is methylene, and R and R are both hydrogen, when W is vinylene. The invention is further directed to methods of treating various CNS and other disorders using said compounds and pharmaceutical compositions thereof.