144603-08-7

Basic information

• Product Name: 6-FLUORO-4-HYDROXY-3-PHENYLQUINOLIN-2(1H)-ONE
• Synonyms: 6-FLUORO-4-HYDROXY-3-PHENYLQUINOLIN-2(1H)-ONE;AURORA KA-3414
• CAS NO: 144603-08-7
• Molecular Formula: C₁₅H₁₀FNO₂
• Molecular Weight: 255.24
• Mol File: 144603-08-7.mol

Chemical Properties

• Boiling Point: 415.7°Cat760mmHg
• Flash Point: 205.2°C
• Appearance: /
• Density: 1.391g/cm³
• Vapor Pressure: 1.18E-07mmHg at 25°C
• Refractive Index: 1.657
• CAS DataBase Reference: 6-FLUORO-4-HYDROXY-3-PHENYLQUINOLIN-2(1H)-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-FLUORO-4-HYDROXY-3-PHENYLQUINOLIN-2(1H)-ONE(144603-08-7)
• EPA Substance Registry System: 6-FLUORO-4-HYDROXY-3-PHENYLQUINOLIN-2(1H)-ONE(144603-08-7)

Safety Data

• Hazardous Substances Data: 144603-08-7(Hazardous Substances Data)

Usage

InChI:InChI=1/C15H10FNO2/c16-10-6-7-12-11(8-10)14(18)13(15(19)17-12)9-4-2-1-3-5-9/h1-8H,(H2,17,18,19)

Upstream product

• 83-13-6 diethyl 2-phenylmalonate 
• 371-40-4 4-fluoroaniline 
• 875930-15-7 4-fluoro-2-(phenylethynyl)aniline 
• 124-38-9 carbon dioxide 
• 61272-76-2 4-fluoro-2-iodoaniline 
• 536-74-3 phenylacetylene 
• 1259521-33-9 3-(4-fluorophenylamino)-3-oxo-2-phenylpropanoic acid 
• 1259521-32-8 ethyl 3-(4-fluorophenylamino)-3-oxo-2-phenylpropanoate 

Downstream Products

• 144619-46-5 3-Chloro-6-fluoro-3-phenyl-1H-quinoline-2,4-dione 
• 145270-05-9 3,6-Difluoro-3-phenyl-1H-quinoline-2,4-dione 
• 1610555-89-9 4-butoxy-6-fluoro-3-phenyl-2(1H)-quinolinone 
• 274691-28-0 2,4-dichloro-6-fluoro-3-phenylquinoline 
• 1259521-34-0 4-chloro-2-ethyl-6-fluoro-3-phenylquinoline 
• 1259521-38-4 1-(6-fluoro-4-(methylsulfonyl)-3-phenylquinolin-2-yl)ethanamine 
• 1259521-29-3 4-amino-6-(1-(6-fluoro-4-(methylsulfonyl)-3-phenylquinolin-2-yl)ethylamino)-pyrimidine-5-carbonitrile 
• 1259523-31-3 4-amino-6-(((1S)-1-(6-fluoro-4-(methylsulfonyl)-3-phenyl-2-quinolinyl)ethyl)amino)-5-pyrimidinecarbonitrile 
• 1259521-61-3 2-(1-bromoethyl)-6-fluoro-4-methoxy-3-phenylquinoline 
• 1259521-63-5 2-(1-(6-Fluoro-4-methoxy-3-phenylquinolin-2-yl)ethyl)isoindoline-1,3-dione 
• 1259521-64-6 2-(1-(6-fluoro-4-hydroxy-3-phenylquinolin-2-yl)ethyl)isoindoline-1,3-dione 
• 1308264-55-2 C₁₈H₁₇FN₂O 
• 1308272-31-2 C₁₇H₁₅FN₂O 
• 1259521-65-7 4-Amino-6-(1-(6-fluoro-4-methoxy-3-phenylquinolin-2-yl)ethylamino)pyrimidine-5-carbonitrile 

Relevant articles and documents

Design, synthesis and antitubercular potency of 4-hydroxyquinolin-2(1H)-ones

In this study, a 50-membered library of substituted 4-hydroxyquinolin-2(1H)-ones and two closely related analogues was designed, scored in-silico for drug likeness and subsequently synthesized. Thirteen derivatives, all sharing a common 3-phenyl substituent showed minimal inhibitory concentrations against Mycobacterium tuberculosis H37Ra below 10 μM and against Mycobacterium bovis AN5A below 15 μM but were inactive against faster growing mycobacterial species. None of these selected derivatives showed significant acute toxicity against MRC-5 cells or early signs of genotoxicity in the Vitotox assay at the active concentration range. The structure activity study relation provided some insight in the further favourable substitution pattern at the 4-hydroxyquinolin-2(1H)-one scaffold and finally 6-fluoro-4-hydroxy-3-phenylquinolin-2(1H)-one (38) was selected as the most promising member of the library with a MIC of 3.2 μM and a CC50 against MRC-5 of 67.4 μM.

Synthesis and SAR study of potent and selective PI3Kδ inhibitors

2,3,4-Substituted quinolines such as (10a) were found to be potent inhibitors of PI3Kδ in both biochemical and cellular assays with good selectivity over three other class I PI3K isoforms. Some of those analogs showed favorable pharmacokinetic properties.

Cu(i)-catalyzed chemical fixation of CO2 with 2-alkynylaniline into 4-hydroxyquinolin-2(1H)-one

A copper(i) catalyzed reaction of 2-alkynylaniline with CO2 using DBU as base to produce 4-hydroxyquinolin-2(1H)-one derivatives in moderate to good yield is presented. In this reaction, a unique bond cleavage pattern for CO2 was observed that one of the C-O double bonds of CO 2 was totally broken and rearranged into two moieties in the absence of the reductive reagent. This efficient reaction system showed the wide generality of substrates including nitro, bromo, cyano and methoxylcarbonyl groups. A possible mechanism containing isocyanate intermediate is proposed. This journal is the Partner Organisations 2014.

Efficient preparation of 4-hydroxyquinolin-2(1 H)-one derivatives with silver-catalyzed carbon dioxide incorporation and intramolecular rearrangement

Although 4-hydroxyquinolin-2(1H)-one derivatives have attracted much attention due to their biological benefits, conventional reactions under harsh heat conditions must be employed to provide these key compounds. In the presence of a catalytic amount of s

HETEROCYCLIC COMPOUNDS AND THEIR USES

Substituted bicyclic heteroaryls and compositions containing them, for the treatment of general inflammation, arthritis, rheumatic diseases, osteoarthritis, inflammatory bowel disorders, inflammatory eye disorders, inflammatory or unstable bladder disorders, psoriasis, skin complaints with inflammatory components, chronic inflammatory conditions, including but not restricted to autoimmune diseases such as systemic lupus erythematosis (SLE), myestenia gravis, rheumatoid arthritis, acute disseminated encephalomyelitis, idiopathic thrombocytopenic purpura, multiples sclerosis, Sjoegren's syndrome and autoimmune hemolytic anemia, allergic conditions including all forms of hypersensitivity. The present invention also enables methods for treating cancers that are mediated, dependent on or associated with p110δ activity, including but not restricted to leukemias, such as Acute Myeloid leukaemia (AML) Myelo-dysplastic syndrome (MDS) myelo-proliferative diseases (MPD) Chronic Myeloid Leukemia (CML) T-cell Acute Lymphoblastic leukaemia (T-ALL) B-cell Acute Lymphoblastic leukaemia (B-ALL) Non Hodgkins Lymphoma (NHL) B-cell lymphoma and solid tumors, such as breast cancer.

Synthesis and cytotoxic activity evaluation of indolo-, pyrrolo-, and benzofuro-quinolin-2(1H)-ones and 6-anilinoindoloquinoline derivatives.

Certain indolo-, pyrrolo-, and benzofuro-quinolin-2(1H)-ones 4a,b, 6, 8, 16a-c and 6-anilinoindoloquinoline derivatives 10a,b, 11a,b, 12a,b have been synthesized and evaluated in vitro against a 3-cell lines panel consisting of MCF7 (Breast), NCI-H460 (Lu

Halogenation Reactions in Position 3 of Quinoline-2,4-dione Systems by Electrophilic Substitution and Halogen Exchange

3-Substituted 4-hydroxy-2(1H)-quinolones 3, 5, 7 are halogenated with bromine or sulfuryl chloride to yield the quinolinediones 9 or 10.Reactions of 3, 5, 7 with chloroform gives the dichloromethyl quinolinediones 11.Halogen exchange leads from the chloro quinolinediones 10 to fluoro quinolinedones 12 and to azido quinolinediones 13.Similarly the dichloro quinolinediones 10an reacts to the difluoro quinolinedione 14, which is reduced to the 3-fluoro-4-hydroxyquinolone 16 and reacts again with sulfuryl chloride to give the mixed 3-chloro-3-fluoroquinolinedione 15.Keywords.Fluorination; 4-Hydroxy-2(1H)-quinolones, 3-alkyl/3-aryl/3-fluoro; 1-Hydroxy-benzoquinolizine-3-ones, 2-alkyl/3-aryl; Quinoline-2,4(1H,3H)-diones, 3-azido-3-alkyl/3-aryl, 3-bromo-3-alkyl/3-aryl, 3-chloro-3-alkyl/3-aryl, 3-fluoro-3-alkyl/3-aryl, 3-dichloromethyl-3-alkyl/3-aryl, 3-chloro-3-fluoro.