71738-83-5

Basic information

• Product Name: 8-Fluoroquinolin-2(1H)-one
• Synonyms: 8-Fluoroquinolin-2(1H)-one;8-Fluoro-2-hydroxyquinoline
• CAS NO: 71738-83-5
• Molecular Formula: C₉H₆FNO
• Molecular Weight: 163.1484432
• Mol File: 71738-83-5.mol

Chemical Properties

• Boiling Point: 332.1±42.0 °C(Predicted)
• Appearance: /
• Density: 1.291±0.06 g/cm3(Predicted)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 10.52±0.70(Predicted)
• CAS DataBase Reference: 8-Fluoroquinolin-2(1H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 8-Fluoroquinolin-2(1H)-one(71738-83-5)
• EPA Substance Registry System: 8-Fluoroquinolin-2(1H)-one(71738-83-5)

Safety Data

• Hazardous Substances Data: 71738-83-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
8-Fluoroquinolin-2(1H)-one is used as a pharmaceutical agent for its antimicrobial properties, serving as a potential treatment for bacterial infections. Its ability to target and inhibit microbial growth makes it a promising candidate for developing new antibiotics.
8-Fluoroquinolin-2(1H)-one is also used as an antiviral agent, leveraging its potential to inhibit viral replication and reduce the severity of viral infections. This application is crucial in the development of treatments for various viral diseases.
In the realm of antiparasitic applications, 8-Fluoroquinolin-1(2H)-one is utilized for its ability to combat parasitic infections, offering a potential therapeutic solution for diseases caused by parasites.
Cancer Treatment:
8-Fluoroquinolin-2(1H)-one is used as an anticancer agent, where it may exhibit potential in inhibiting the growth and proliferation of cancer cells. Its role in the development of novel cancer therapeutics is significant, as it could contribute to more effective treatment options.
In the field of inflammation management, 8-Fluoroquinolin-2(1H)-one is used for its potential anti-inflammatory properties, which can help in reducing inflammation and alleviating symptoms associated with inflammatory conditions.
Used in Chemical Synthesis:
8-Fluoroquinolin-2(1H)-one is used as a building block in the synthesis of other chemical compounds, particularly in the development of new pharmaceuticals and organic materials. Its unique structure and properties make it a versatile component in various chemical reactions and processes.

Upstream product

• 25893-50-9 N-(2-fluorophenyl)-3-phenylacrylamide 
• 1065481-24-4 (2E)-N-(2-fluorophenyl)-3-phenylprop-2-enamide 
• 394-68-3 8-fluoroquinoline 
• 2795-43-9 8-fluoroquinoline-N-oxide 
• 348-54-9 2-Fluoroaniline 
• 6191-99-7 (2E)-3-ethoxyprop-2-enoyl chloride 
• 124467-23-8 2-chloro-8-fluoroquinoline 

Downstream Products

• 124467-23-8 2-chloro-8-fluoroquinoline 
• 1065481-27-7 (R)-1-(2-chloro-8-fluoroquinolin-3-yl)ethanol 
• 1464832-35-6 2-((1S)-1-(8-fluoro-2-(2-(methylthio)phenyl)quinolin-3-yl)ethyl)isoindoline-1,3-dione 
• 1464832-37-8 2-((1S)-1-(8-fluoro-2-(2-(methylsulfonyl)phenyl)-3-quinolinyl)ethyl)-1H-isoindole-1,3(2H)-dione 
• 1464832-39-0 (1S)-1-(8-fluoro-2-(2-(methylsulfonyl)phenyl)-3-quinolinyl)ethanamine 
• 1464832-30-1 4-amino-6-(((1S)-1-(8-fluoro-2-(2-(methyl-sulfonyl)phenyl)-3-quinolinyl)ethyl)amino)-5-pyrimidinecarbonitrile 
• 1065478-86-5 N-((S)-1-(8-fluoro-2-(3-fluorophenyl)quinolin-3-yl)ethyl)-9H-purin-6-amine 
• 1065481-30-2 (1S)-1-(8-fluoro-2-(3-fluorophenyl)quinolin-3-yl)ethanamine 
• 1065481-29-9 3-((S)-1-azidoethyl)-8-fluoro-2-(3-fluorophenyl)quinoline 
• 1065481-28-8 (S)-3-(1-azidoethyl)-2-chloro-8-fluoro-quinoline 

Relevant articles and documents

Efficient visible light mediated synthesis of quinolin-2(1H)-ones from quinolineN-oxides

Quinolin-2(1H)-ones are one of the important classes of compounds due to their prevalence in natural products and in pharmacologically useful compounds. Here we present an unconventional and hitherto unknown photocatalytic approach to their synthesis from easily available quinoline-N-oxides. This reagent free highly atom economical photocatalytic method, with low catalyst loading, high yield and no undesirable by-product, provides an efficient greener alternative to all conventional synthesis reported to date. The robustness of the methodology has been successfully demonstrated with easy scaling up to the gram scale.

Heterocoumarins Are Selective Carbonic Anhydrase IX and XII Inhibitors with Cytotoxic Effects against Cancer Cells Lines

We have synthesized a new series of coumarin-based compounds demonstrating high selectivity and potent effects with low nanomolar affinity against the tumor associated carbonic anhydrase (CA, EC 4.2.1.1) isoforms hCA IX and XII. A number of these compounds were evaluated ex vivo against human prostate (PC3) and breast (MDA-MB-231) cancer cell lines. Compounds 4b and 15 revealed effective cytotoxic effects after 48 h of incubation in both normoxic and hypoxic conditions with PC3 cancer cell line. However, compound 3 showed selective cytotoxic effects against MDA-MB-231 in hypoxic condition. These results may be of particular importance for the choice of future drug candidates targeting hypoxic tumors and metastases, considering the fact that a selective carbonic anhydrase CA IX inhibitor (SLC-0111) is presently in phase II clinical trials.

Scalable and Practical Synthesis of Halo Quinolin-2(1H)-ones and Quinolines

A practical and scalable synthesis of halo quinolin-2(1H)-ones is presented. The heterocycles are easily accessed from inexpensive halo anilines in a two-step sequence. The anilines are acylated with methyl 3,3-dimethoxypropionate under basic conditions in quantitative yields. The crude amides undergo cyclization in sulfuric acid to the desired halo quinolin-2(1H)-ones in 28-93% yield (2 steps). The synthetic sequence was successfully applied on 800 g scale. Anilines with strong electron withdrawing or electron donating groups were poor substrates for this procedure. 6-Iodoquinolin-2(1H)-one and 6-bromo-8-iodoquinolin-2(1H)-one were further functionalized to obtain quinolines substituted with various functional groups.

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.

TRIAZOLOPYRIDINE COMPOUNDS AS PIM KINASE INHIBITORS

Compounds of Formula (I), in which A, B, R1, R1a, R2, R3, R4, R5, R6, and R7 have the meanings given in the specification, are receptor tyrosine inhibitors useful in the treatment of immune cell-associated diseases and disorders, such as inflammatory and autoimmune diseases.

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 p110 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.