105024-96-2

Usage

Type of compound

Synthetic chemical compound

Potential medicinal properties

Inhibits the growth of cancer cells

Other properties

Antioxidant and anti-inflammatory

Research status

Preclinical studies; ongoing research for potential applications in medicine

Structure

Contains a benzyl group attached to a hydroxyquinoline ring

Unique properties

Chemical and biological properties due to the presence of the benzyl and hydroxyquinoline groups

Upstream product

• 141-82-2 malonic acid 
• 758640-21-0 N-Benzylaniline 
• 118-48-9 isatoic anhydride 
• 1373442-14-8 ethyl 3-(benzyl (phenyl)amino)-3-oxopropanoate 
• 130058-54-7 ethyl 4-hydroxy-2-oxo-1-(phenylmethyl)-1,2-dihydro-3-quinolinecarboxylate 
• 20877-86-5 N-phenyl isatoic anhydride 

Downstream Products

• 223668-13-1 1-benzyl-3-diazoquinoline-2,4-dione 

Relevant academic research and scientific papers

Efficient synthesis of bicyclo[3.3.1]nonane systems via tandem 1,3-dinucleophilic addition of 4-hydroxy-2-quinolinones to quinolinium salts

The synthesis of bicyclo[3.3.1]nonane systems is reported. The synthesis is based on the tandem 1,3-dinucleophilic addition of 4-hydroxy-2-quinolinone to quinolinium salts.

Asymmetric synthesis of tetrahydropyran[3,2-c]quinolinones via an organocatalyzed formal [3 + 3] annulation of quinolinones and MBH 2-naphthoates of nitroolefin

An efficient asymmetric and enantio-swithchable organocatalytic [3 + 3] annulation reaction using MBH-2-naphthoates of nitroalkenes and 4-hydroxyquinolin-2(1H)-ones has been developed. Densely substituted tetrahydropyrano[3,2-c]quinolinones scaffolds with two adjacent stereogenic centers are obtained with high yield (up to 95% yield) and good stereoselectivities (up to >20:1 dr and 96% ee) in an enantio-switchable manner. Furthermore, gram scale synthesis was achieved and the nitro group could easily transform into an amino group without any appreciable loss in the diastereo- and enantioselectivity.

Anti-infective agents

Compounds having the formula are hepatitis C (HCV) polymerase inhibitors. Also disclosed are a composition and method for inhibiting hepatitis C (HCV) polymerase, processes for making the compounds, and synthetic intermediates employed in the processes.

Rhodium-Mediated Dipolar Cycloaddition of Diazoquinolinediones

As an entry to furoquinoline structures of natural origin, the rhodium-mediated dipolar cycloaddition of diazoquinolinediones with alkenes and alkynes has been examined. Because of the unsymmetrical nature of the diazo compounds, both linear and angular furoquinoline products are possible. For the most part, a mixture of regioisomers is generated in moderate to good yields, though in a few cases dominant products are obtained in high yields. The products can be further converted to naturally occurring alkaloids such as isodictamnine. A novel observation in this work is that catalytic quantities of acid enhance the yield and regiochemical control in the cycloaddition.

Acyl and alkoxy substituted quinolines

Compounds useful as antiviral agents against DNA-containing viruses, such as herpes group viruses, are disclosed. The compounds are are represented by compounds of Formula 1.0: STR1 and their pharmaceutically acceptable salts and solvates. Pharmaceutical compositions containing compounds represented by Formula 1.0 and methods of treating a viral infection using compounds represented by Formula 1.0 are disclosed. Also disclosed are compounds useful as antihypertensive agents and methods of treating hypertension using such compounds. The antihypertensive agents are compounds represented by Formula 1.0 wherein R4 is selected from the group consisting of alkyl and aminoalkyl. Preferably R1 is H.

Alkyl and acyl substituted quinolines

Compounds useful as antiviral agents against DNA-containing viruses, such as herpes group viruses, are disclosed. The compounds are represented by Formula 1.0: STR1 and their pharmaceutically acceptable salts and solvates; wherein: (A) X is selected from

Syntheses of 3-Acyl-4-hydroxy-2(1H)-quinolones

3-Acyl-4-hydroxy-2(1H)-quinolones 5 are obtained by hydrolytic ring opening and subsequent decarboxylation from the corresponding pyranoquinolin-2,5(6H)-diones 4, which in turn are easily obtained from 1:2 condensation of of anilines 1 with diethyl malonate 2a or 1:1 condensation of diethyl alkyl- or arylmalonates 2b-e with 4-hydroxy-2(1H)-quinolones 3.Nitropyranoquinolinediones 6 furnish after ringopening 3-nitroacetyl-4-hydroxy-2(1H)-quinolones 8.Pyranoquinolines 7 and 9 with acetyl- or aminosubstituents are hydrolyzed during basic ringopening to yield 5.

Antiviral quinolinone compounds

Compounds useful as antiviral agents against DNA containing viruses, such as herpes group viruses, are disclosed. The compounds are selected from the group consisting of: STR1 and their pharmaceutically acceptable salts and solvates. Pharmaceutical compositions containing compounds represented by Formula 1.0 are disclosed. Also disclosed are methods of treating a viral infection using compounds represented by Formula 1.0. A process for making compounds of Formula 1.0 from the appropriate 3-oximino-quinolin-2,4(1H)-dione (Formula 2.5) is also disclosed. The process comprises reductively hydrolyzing an appropriate 3-oximino-quinolin-2,4(1H)-dione (Formula 2.5) in a mixture with a hydrogenation catalyst and an acidic solvent mixture.

Certain N-substituted 3-oximino-2,4-dioxoquinolin-2,4-(1H)diones useful for treating viral infections

Compounds useful as antiviral agents against DNA containing viruses, such as herpes group viruses, are disclosed. The compounds are selected from the group consisting of: STR1 and their pharmaceutically acceptable salts and solvates. Pharmaceutical compos