16619-14-0

Usage

Uses

Used in Pharmaceutical Industry:
2-PHENYL-2,3-DIHYDRO-4-QUINOLONE is used as a pharmaceutical compound for its demonstrated anti-inflammatory properties, making it a candidate for the development of drugs to treat inflammation-related conditions.
Used in Antibacterial Applications:
In the field of infectious diseases, 2-PHENYL-2,3-DIHYDRO-4-QUINOLONE is utilized as an antibacterial agent, targeting a range of bacterial infections due to its ability to disrupt bacterial cell functions.
Used in Antifungal Applications:
2-PHENYL-2,3-DIHYDRO-4-QUINOLONE is employed as an antifungal agent, effective against various fungal infections, leveraging its capacity to inhibit fungal growth and proliferation.
Used in Medicinal Research:
In the realm of medical and biological research, 2-PHENYL-2,3-DIHYDRO-4-QUINOLONE serves as a key compound for studying its potential role in treating a variety of diseases and conditions, given its multifaceted biological activities.

InChI:InChI=1/C15H13NO/c17-15-10-14(11-6-2-1-3-7-11)16-13-9-5-4-8-12(13)15/h1-9,14,16H,10H2

Upstream product

• 78396-00-6 2-aminochalcone 
• 551-93-9 2-aminoacetophenone 
• 100-52-7 benzaldehyde 
• 78396-00-6 1-(2-aminophenyl)-3-phenylprop-2-en-1-one 
• 577-59-3 2-acetylnitrobenzene 
• 53744-32-4 (2E)-1-(2-nitrophenyl)-3-phenyl-2-propen-1-one 
• 1352449-02-5 1-(2-((2-iodobenzyl)amino)phenyl)ethan-1-one 
• 5159-41-1 2-iodobenzyl alcohol 
• 40400-13-3 2-Iodobenzyl bromide 
• 108-73-6 3,5-dihydroxyphenol 
• 169797-22-2 1-(2-aminophenyl)-3-phenyl-propan-1-one 
• 100-51-6 benzyl alcohol 
• 148564-90-3 2,2,2-trifluoro-N-(2-(3-hydroxy-3-phenylprop-1-ynyl)phenyl)acetamide 
• 155694-57-8 [E]-3-phenyl-1-(2-trifluoroacetamidophenyl)prop-2-en-1-one 

Downstream Products

• 60355-89-7 4-Acetoxy-1-acetyl-1,2-dihydro-2-phenylquinoline 
• 60355-81-9 1-N-acetyl-4-keto-2-phenyl-1,2,3,4-tetrahydroquinoline 
• 143237-75-6 <1,2,3,4-tetrahydro-2-phenylquinolin-4-one> thiosemicarbazone 
• 113544-25-5 2-Oxo-2-{N'-[(R)-2-phenyl-2,3-dihydro-1H-quinolin-(4E)-ylidene]-hydrazino}-N-(1-phenyl-ethyl)-acetamide 
• 113544-25-5 2-Oxo-2-{N'-[(S)-2-phenyl-2,3-dihydro-1H-quinolin-(4E)-ylidene]-hydrazino}-N-(1-phenyl-ethyl)-acetamide 
• 14802-18-7 2-phenyl-1H-quinolin-4-one 
• 107468-41-7 2-Phenyl-1,2,3,4-tetrahydro-benzo[e][1,4]diazepin-5-one 
• 22680-62-2 4-methoxy-2-phenyl-quinoline 
• 918165-52-3 2-phenyl-1,2,3,4-tetrahydro-quinolin-4-ol 
• 113567-28-5 (S)-2-phenyl-2,3-dihydroquinolin-4(1H)-one 
• 113567-29-6 (R)-2-phenyl-2,3-dihydroquinolin-4(1H)-one 
• 1133158-36-7 6-chloro-2-phenyl-2,3-dihydroquinolin-4(1H)-one 
• 1171953-00-6 2-phenyl-3-((pyridin-4-yl)methyl)quinolin-4(1H)-one 
• 1144-20-3 2-phenyl-4-quinolinol 

Relevant academic research and scientific papers

Straightforward Synthesis of Novel 4-Styrylquinolines/4-Styrylquinolin-2-ones and 9-Styryldihydroacridin-1(2 H)-ones from Substituted 2′-Aminochalcones

An alternative and efficient one-step approach to develop small libraries of polysubstituted 4-styrylquinolines/4-styrylquinolin-2-ones and 9-styryldihydroacridin-1-ones is described. According to this approach, new series of these compounds were straightforwardly synthesized in high yields starting from synthetically available 2′-aminochalcones and 1,3-dicarbonyl compounds in glacial acetic acid as a catalyst via the Friedl?nder reaction. Our approach also offers an expeditious way to access novel molecular hybrids in whose structures styryl and chalcone fragments are attached at the C4 and C3 positions, respectively, of the quinoline ring. All synthesized compounds were fully characterized by means of IR, HRMS and NMR techniques, and most were screened at the National Cancer Institute, USA, for their antitumor activity.

A Novel Approach to N-Tf 2-Aryl-2,3-Dihydroquinolin- 4(1H)-ones via a Ligand-Free Pd(II)-Catalyzed Oxidative Aza-Michael Cyclization

2-Aryl-2,3-dihydroquinolin-4(1H)-ones have recently been identified as important structures with potent biological activities such as antitumor and antidiabetic effect. Herein, a total of 25 novel N-Tf 2-aryl-2,3-dihydroquinolin-4(1H)-ones were expediently synthesized via the oxidative aza-Michael cyclization of N-Tf-2′-aminodihydrochalcones by ligand-free palladium(II) catalysis. This study presents a new synthetic approach to yield N-Tf 2-aryl-2,3-dihydroquinolin-4(1H)-ones, which can be easily transformed into pharmacologically interesting aza-flavanones and other N-heterocycles, such as quinolines and tetrahydroquinolines, in yields up to 84 %. This methodology has various advantages, which includes short reaction times under mild conditions and suitable functional group tolerance. Furthermore, a plausible mechanism was proposed and demonstrated by kinetic analysis.

Chelating Group Enabled Palladium-Catalyzed Regiodivergent Carbonylative Synthesis of 2,3-Dihydroquinolin-4(1H)-ones

A new procedure on palladium-catalyzed carbonylative cyclization of N-(2-pyridyl)sulfonyl (N-SO2Py)-2-iodoanilines with terminal alkenes has been developed for the rapid construction of dihydroquinolin-4(1H)-one scaffolds. Enabled by the chelat

Organometallic titanocene complex as highly efficient bifunctional catalyst for intramolecular Mannich reaction

Bifunctional catalysts bearing two catalytic sites, Lewis acidic organometallic titanocene and Br?nsted acidic COOH, have been assembled in situ from Cp2TiCl2 with carboxylic acid ligands, showing high catalytic activity over an intramolecular Mannich reaction towards synthesis of 2-aryl-2,3-dihydroquinolin-4(1H)-ones. The determination of the bifunctional catalyst Cp2Ti(C8H4NO6)2 was elucidated by single X-ray HR-MS and investigation of catalytic behavior. In particular, masking the Br?nsted acidic COOH catalytic site with dormant COOMe lowered the reaction yield greatly, indicating that two catalytic sites work together to maintain high catalytic efficiency.

Transformation of fluorinated 2-alkynylanilines by various catalytic systems

Simple and efficient approaches to the synthesis of fluorinated benzoazaheterocycles with good yields are reported. Firstly a series of polyfluorinated 2-alkynylanilines – the versatile building blocks – was synthesized by the Sonogashira reaction of o-iodoaniline with terminal alkynes. Then the transformations of the obtained 2,3,4-trifluo-6-alkynilanilines in the presence of KOH or PdCl2 in MeCN, and in the presence of monohydrate of p-toluenesulfonic acid (p-TSA?H2O) in MeOH, EtOH or benzene were investigated. It was found that Ph- and n-Bu-containing alkynylanilines by action of PdCl2 in MeCN underwent an intramolecular cyclization reaction to produce the corresponding indoles in high yields. The reaction of KOH with alkynes containing the tertiary alcohol function at the triple bond produced the unsubstituted on the pyrrole ring indole. It was found that fluorinated 2-alkynilanilines can be transformated into indoles, 2-arylketones and 2,3-dihydroquinolines by action of p-TSA?H2O in boiling alcohols, depending on the substituent at the triple bond. The use of benzene as a solvent in the reaction of p-TSA?H2O with polyfluorinated alkynes, bearing an alcohol group resulted in representative series of 2,3-dihydroquinolinones containing a substituents R1 and R2 in the 2nd position of their structure (R = H, H; Me, Me; H, i-Pr; H, Ph).

Titanocene complex with oxygen-containing carboxylic acid as ligand as well as preparation method and application of titanocene complex

The invention discloses a titanocene complex with oxygen-containing carboxylic acid as well as a preparation method and an application of the titanocene complex. The structural formula of the complexis shown in the description. The titanocene complex is p

Zirconyl Nitrate as an Efficient Catalyst for Facile Synthesis of 2-Aryl-2,3-dihydroquinolin-4(1 H)-one Derivatives in Aqueous Medium

A simple, green, and efficient method is introduced for the synthesis of 2-aryl-2,3-dihydroquinolin-4(1 H)-ones under mild reaction conditions with improved yields by intramolecular cyclization of o -aminochalcones with zirconyl nitrate [Zn(O)(NO 3/

2-aryl-2,3-dihydro-4(1H)-quinolinone semicarbazone compound and application thereof

The invention relates to the field of medicine technology, and a series of novel 2-aryl-2,3-dihydrogen-4(1H)-quinolinone semicarbazone derivatives (I) and pharmaceutically acceptable salts, solvates,optical isomers or polymorphs are designed and synthesized. The derivative (I) and its pharmaceutically acceptable salt, solvate, optical isomer or polymorph can be mixed as an active ingredient witha pharmaceutically acceptable carrier to prepare a pharmaceutical composition. A double dilution method is used for test of the antifungal activity of the derivative (I) and its pharmaceutically acceptable salt, solvate, optical isomer or polymorph, and the results show that the derivative has stronger killing effect on clinically common pathogenic fungi, and is expected to overcome the defects oflarge toxic and side effects, easy generation of drug resistance of azole antifungal medicines which are widely used clinically. The specific formula is shown in the description.

Method for synthesizing 2-aryl-2,3-dihydro-4(1H)-quinolinone derivative under catalysis of high-acidity ionic liquid

The invention discloses a method for synthesizing a 2-aryl-2,3-dihydro-4(1H)-quinolinone derivative under the catalysis of high-acidity ionic liquid, belonging to the technical field of chemical material preparation. According to the method, o-aminoacetophenone and aromatic aldehyde are used as reaction raw materials and subjected to a reaction under the catalysis of a high-acidity ionic liquid catalyst so as to synthesize the 2-aryl-2,3-dihydro-4(1H)-quinolinone derivative. Through selection of specific high-acidity ionic liquid as the catalyst and optimization of reaction process parameters, the method provided by the invention can effectively overcome the disadvantages of great usage amounts of catalysts, poor recycling performance, complex product purification process and insufficient product yield in conventional synthesis processes.

Synthesis, molecular modeling and biological evaluation of aza-flavanones as α-glucosidase inhibitors

An efficient acid catalyzed methodology has been employed to synthesize a variety of aza-flavanones and their α-glucosidase inhibitory activity is evaluated using acarbose, miglitol and voglibose as reference standards. Molecular modeling studies were per