14994-75-3

Usage

InChI:InChI=1/C15H11NO2/c17-14-10-15(18)16(11-6-2-1-3-7-11)13-9-5-4-8-12(13)14/h1-10,17H

Upstream product

• 54289-77-9 3-acetyl-4-hydroxy-1-phenylquinolin-2(1H)-one 
• 122-39-4 diphenylamine 
• 1663-67-8 malonoyl dichloride 
• 91-40-7 2-(phenylamino)benzoic acid 
• 108-24-7 acetic anhydride 
• 65050-85-3 ethyl 3-(diphenylamino)-3-oxopropanoate 
• 54091-20-2 3-(diphenylamino)-3-oxopropanoic acid 
• 105-53-3 diethyl malonate 
• 1399325-43-9 5-phenyl[1,3]oxathiolo[4,5-c]quinoline-2,4(5H)-dione 
• 1399324-00-5 3-benzyl-1,2,3,4-tetrahydro-2,4-dioxo-1-phenylquinolin-3-yl thiocyanate 
• 18706-64-4 4-hydroxy-6-phenyl-2H-pyrano<3,2-c>quinoline-2,5(6H)-dione 
• 148838-17-9 7-(Diphenylamino)-4-methoxy-2,5-dioxo-N,N-diphenyl-2H,5H-pyrano<4,3-b>pyran-8-carboxamid 
• 148838-13-5 7-(Diphenylamino)-4-hydroxy-2,5-dioxo-N,N-diphenyl-2H,5H-pyrano<4,3-b>pyran-8-carboxamid 
• 141-82-2 malonic acid 

Downstream Products

• 134369-73-6 2,3-Dimethyl-5-phenyl-5H-furo[3,2-c]quinolin-4-one 
• 106058-79-1 C₃₈H₂₈N₂O₄ 
• 134369-76-9 3-(4-Chloro-phenoxymethyl)-2-methyl-5-phenyl-5H-furo[3,2-c]quinolin-4-one 
• 134369-78-1 3-(2-Chloro-phenoxymethyl)-2-methyl-5-phenyl-5H-furo[3,2-c]quinolin-4-one 
• 54675-12-6 4-hydroxy-3-nitro-1-phenyl-2(1H)-quinolone 
• 110254-63-2 4-chloro-1-phenyl-2(1H)-quinolone 
• 106058-78-0 C₃₇H₂₆N₂O₄ 
• 82153-58-0 6-Phenyl-4-propyl-6H-pyrano[3,2-c]quinoline-2,5-dione 
• 121673-75-4 2-Methyl-5-phenyl-5H-furo[3,2-c]quinolin-4-one 
• 121673-65-2 1-Phenyl-3,3-di-prop-2-ynyl-1H-quinoline-2,4-dione 
• 128881-46-9 5-Phenyl-5H,12H-7-thia-5,12-diaza-benzo[a]anthracen-6-one 
• 126936-74-1 4-(2-Oxo-2-p-tolyl-ethoxy)-1-phenyl-1H-quinolin-2-one 
• 126936-75-2 4-[2-(4-Chloro-phenyl)-2-oxo-ethoxy]-1-phenyl-1H-quinolin-2-one 
• 110216-89-2 1-Phenyl-4-tosyloxy-2(1H)-chinolon 

Relevant academic research and scientific papers

4-Hydroxy-1-phenylquinolin-2(1H)-one in One-pot Synthesis of Pyrimidoquinolines and Related Compounds under Microwave Irradiation and Conventional Conditions

Biginelli condensation reactions of 4-hydroxy-1-phenylquinolin-2(1H)-one, aryl aldehydes and urea, or thiourea, 5-amino-1H-1,2,4-triazole, or 2-amine-1H-benzimidazole (9) under microwave irradiation afforded the corresponding pyrimido[5,4-c]quinolin-5-one derivatives in high yields. One-pot synthesis of 2H-pyrano[3,2-c]quinolines is also reported.

Design, synthesis, in vitro antiproliferative evaluation and in silico studies of new VEGFR-2 inhibitors based on 4-piperazinylquinolin-2(1H)-one scaffold

Angiogenesis is essential in the growth of solid tumors which need oxygen and nutrients supply to grow in size. The VEGF/VEGFR-2 signaling pathway plays an important role in tumor angiogenesis. Sorafenib is an FDA approved cancer therapeutic with activity

One-step Synthesis of 3-Unsubstituted 4-Hydroxy-2(1H)-Quinoline

3-Unsubstituted 4-hydroxy-2(1H)-quinolone (DHQ) derivatives were synthesized from aniline derivatives and diethyl malonate at low temperature using AlCl3 as catalyst and Eaton reagent as acidic environment. A reaction mechanism was proposed and elucidated. Different synthetic intermediates are specially prepared or purified and used to understand the reaction and validation mechanism.

Novel 4-(piperazin-1-yl)quinolin-2(1H)-one bearing thiazoles with antiproliferative activity through VEGFR-2-TK inhibition

A new series of 2-(4-(2-oxo-1,2-dihydroquinolin-4-yl)piperazin-1-yl)-N-(4-phenylthiazol-2-yl)acetamide derivatives were synthesized and evaluated for anticancer activity. All target compounds showed anticancer activity higher than that of their 2-oxo-4-piperazinyl-1,2-dihydroquinolin-2(1H)-one precursors. Multidose testing of target compounds was performed against breast cancer T-47D cell line. Five compounds showed higher cytotoxic activity than Staurosporine. The dihalogenated derivative showed the best cytotoxic activity with IC50 2.73 ± 0.16 μM. In addition, the VEGFR-2 inhibitory activity of all synthetic compounds was evaluated. Two compounds of 6-fluoro-4-(piperazin-1-yl)quinolin-2(1H)-ones showed inhibitory activity comparable to sorafenib with IC50 46.83 ± 2.4, 51.09 ± 2.6 and 51.41 ± 2.3 nM, respectively. The cell cycle analysis of two compounds namely, 2-(4-(6-fluoro-2-oxo-1,2-dihydroquinolin-4-yl)piperazin-1-yl)-N-(4-phenylthiazol-2-yl)acetamide and N-(4-(4-chlorophenyl)thiazol-2-yl)-2-(4-(2-oxo-1-phenyl-1,2-dihydroquinolin-4-yl)piperazin-1-yl)acetamide revealed that the arrest of cell cycle occurred at S phase. In apoptosis assay, the same two compounds were able to induce significant levels of early and late apoptosis. In a similar manner to Sorafenib, docking of target compounds with VEGFR-2 protein 4ASD showed HB with Cys919 in hinge region of enzyme and HB with both Glu885 and Asp1046 in gate area. Using SwissADME, all target compounds were predicted to be highly absorbed from gastrointestinal tract with no BBB permeability. It is clear that the two compounds are promising antiproliferative candidates that require further optimization.

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.

Modified riemschneider reaction of 3-thiocyanatoquinolinediones

The Riemschneider reaction of 3-thiocyanatoquinoline-2,4(1H,3H)-diones with conc. H2SO4 was investigated. Using different reaction conditions, 13 types of reaction products were isolated. Compounds bearing a Me, Et, or Bu group at C(3) afforded mainly [1,3]thiazolo[5,4-c]quinoline-2,4- diones and 1,9b-dihydro-9b-hydroxythiazolo[5,4-c]quinoline-2,4-diones. In the case of the 3-Bu derivatives of the starting compounds, C-debutylation was also observed. If a Bn group is present at C(3), rapid C-debenzylation of the starting thiocyanates occurred, yielding [1,3]oxathiolo[4,5-c]quinoline-2,4- diones, and mixtures of mono-, di-, and trisulfides derived from 4-hydroxy-3-sulfanylquinoline-2-ones. The reaction mechanism of all of the transformations is discussed. All new compounds were characterized by IR, 1H- and 13C-NMR, and EI and ESI mass spectra, and in some cases, 15N-NMR spectra were also used to characterize new compounds. Copyright

Synthesis of 4-hydroxy-3-formylideneamino-lH/methyl/phenylquinolin-2-ones

An efficient method for the synthesis of 4-hydroxy-3-formylideneamino-l H/methyl/phenylquinolin-2-ones by the condensation of corresponding 4-hydroxy-3-formyl-l///methyl/phenylquinolin-2-one with substituted anilines/aliphatic primary amines is reported. The carboxaldehyde in turn is prepared starting either from substituted anilines or benzoic acid. The structures of compounds are established by the elemental analysis and spectral data.

A convenient one-pot synthesis of pyrano[3,2-c]quinolin-2,5(6H)-dione and 2H,5H-pyrano[3,2-c]chromene-2,5-dione derivatives

The preparation of novel pyrano[3,2-c]quinolin-2,5(6H)-dione and 2H,5H-pyrano[3,2-c]chromene-2,5-dione derivatives starting from 4-hydroxyquinolin-2(1H)-ones and 4-hydroxy-2H-chromene-2-one with chlorocarbonyl ketenes is described. This method provides a new route to produce fused pyrano derivatives in good to excellent yields in a short experimental time. Georg Thieme Verlag Stuttgart.

Malonates in cyclocondensation reactions

The use of malonates such as diethyl malonates 9, (chlorocarbonyl)ketenes 15 and bis(2,4,6-trichlorophenyl) malonates 18 as reagents for cyclocondensation with 1,3-dinucleophiles to give six-membered heterocycles is described. Further attempts to use malonates such as bis(trimethylsilyl) malonates 19 and bis(carbamimidoyl) malonates 29 as new cyclocondensation agents are described.

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.