607-40-9

Basic information

• Product Name: 6-FLUORO-2-HYDROXYQUINOLINE-4-CARBOXYLIC ACID
• Synonyms: 6-FLUORO-2-HYDROXYQUINOLINE-4-CARBOXYLIC ACID;6-fluoro-2-hydroxyquinoline-4-carboxylic acid(SALTDATA: FREE);6-Fluoro-2-oxo-1,2-dihydro-quinoline-4-carboxylic acid
• CAS NO: 607-40-9
• Molecular Formula: C₁₀H₆FNO₃
• Molecular Weight: 207.1579432
• Mol File: 607-40-9.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 475.882 °C at 760 mmHg
• Flash Point: 241.605 °C
• Appearance: /
• Density: 1.57 g/cm³
• Vapor Pressure: 7.3E-10mmHg at 25°C
• Refractive Index: 1.699
• CAS DataBase Reference: 6-FLUORO-2-HYDROXYQUINOLINE-4-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 6-FLUORO-2-HYDROXYQUINOLINE-4-CARBOXYLIC ACID(607-40-9)
• EPA Substance Registry System: 6-FLUORO-2-HYDROXYQUINOLINE-4-CARBOXYLIC ACID(607-40-9)

Safety Data

• Hazardous Substances Data: 607-40-9(Hazardous Substances Data)

Usage

Uses

6-fluoro-2-hydroxyquinoline-4-carboxylic acid (cas# 607-40-9) is a quinoline-carboxamide derivative which is used in the preparation of antimalarial drugs.

InChI:InChI=1/C10H6FNO3/c11-5-1-2-8-6(3-5)7(10(14)15)4-9(13)12-8/h1-4H,(H,12,13)(H,14,15)

Upstream product

• 715-88-8 1-acetyl-5-fluoro-1H-indole-2,3-dione 
• 443-69-6 5-fluoro-1H-indole-2,3-dione 
• 108-24-7 acetic anhydride 
• 141-82-2 malonic acid 
• 15912-69-3 6-fluoro-2-hydroxy-4-methylquinoline 
• 2713-85-1 N-(4-fluorophenyl)-3-oxobutanamide 
• 371-40-4 4-fluoroaniline 
• 351-09-7 N-(4-fluorophenyl)-2-(hydroxyimino) acetamide 

Downstream Products

• 436096-52-5 2-chloro-6-fluoro-4-quinolinecarboxylic acid 
• 1388844-25-4 6-fluoro-2-oxo-1,2-dihydroquinoline-4-carbohydrazide 
• 1388844-20-9 ethyl 6-fluoro-2-oxo-1,2-dihydroquinoline-4-carboxylate 
• 1469439-69-7 6-fluoro-2-[4-(morpholinomethyl)phenyl]-N-(2-pyrrolidin-1-ylethyl)quinoline-4-carboxamide 

Relevant articles and documents

Discovery, synthesis and molecular substantiation of N-(benzo[d]thiazol-2-yl)-2-hydroxyquinoline-4-carboxamides as anticancer agents

The effort was taken to develop a series of benzothiazole and quinoline fused bioactive compounds obtained through a four-step synthetic route using a range of substituted acetoacetanilides. Achieved N-(benzo[d]thiazol-2-yl)-2-hydroxyquinoline-4-carboxamides (6a-l) were produced up to 96% of yield while the eco-friendly p-TSA used as a catalyst. Further, the anticancer activity of these compounds was determined using a range of cancer cell lines starting from MCF-7 (Breast cancer), HCT-116 (Colon cancer), PC-3 & LNCaP (Prostate) and SK-HEP-1 (Liver cancer). Present study compounds were also testified for antioxidant properties prior to anticancer studies since the Reactive Oxygen Species (ROS) being vital in cancer development. To determine the cell membrane stability effects of the compounds, human red blood cells (HRBC) based membrane protection assay was determined. In the results, compounds 6a-l were able to produce a dominated result values over PC3 cell lines (Prostate cancer) than the other cell lines used in this study. Since the connectivity of human germ cell alkaline phosphatase (hGC-ALP) in the development of prostate cancer is known, the most active compounds were evaluated for the hGC-ALP inhibition in order to ensure a mechanism of anticancer action of these compounds. The mode of interaction and binding affinity of these compounds was also investigated by a molecular docking study. In the results, 6d, 6i, 6k, and 6l were found with least IC50 values 0.075 μM and highest relative activity of 92%, 90%, and 96% respectively. The need for further animal model evaluation and pre-clinical studies recognized.

Synthesis and Pharmacological Evaluation of [11C]Granisetron and [18F]Fluoropalonosetron as PET Probes for 5-HT3 Receptor Imaging

Serotonin-gated ionotropic 5-HT3 receptors are the major pharmacological targets for antiemetic compounds. Furthermore, they have become a focus for the treatment of irritable bowel syndrome (IBS) and there is some evidence that pharmacological modulation of 5-HT3 receptors might alleviate symptoms of other neurological disorders. Highly selective, high-affinity antagonists, such as granisetron (Kytril) and palonosetron (Aloxi), belong to a family of drugs (the "setrons") that are well established for clinical use. To enable us to better understand the actions of these drugs in vivo, we report the synthesis of 8-fluoropalonosetron (15) that has a binding affinity (Ki = 0.26 ± 0.05 nM) similar to the parent drug (Ki = 0.21 ± 0.03 nM). We radiolabeled 15 by nucleophilic 18F-fluorination of an unsymmetrical diaryliodonium palonosetron precursor and achieved the radiosynthesis of 1-(methyl-11C)-N-granisetron ([11C]2) through N-alkylation with [11C]CH3I, respectively. Both compounds [18F]15 (chemical and radiochemical purity >95%, specific activity 41 GBq/μmol) and [11C]2 (chemical and radiochemical purity ≥99%, specific activity 170 GBq/μmol) were evaluated for their utility as positron emission tomography (PET) probes. Using mouse and rat brain slices, in vitro autoradiography with both [18F]15 and [11C]2 revealed a heterogeneous and displaceable binding in cortical and hippocampal regions that are known to express 5-HT3 receptors at significant levels. Subsequent PET experiments suggested that [18F]15 and [11C]2 are of limited utility for the PET imaging of brain 5-HT3 receptors in vivo.

Anti-Malarial Agents

The present invention relates to a novel class of quinolone-4-carboxamide Pf3D7 inhibitors of general formula (I) (Formula (I)) wherein R1, R2, R3, R4, R5, R6, R7, R8 and X are as defined herein, to their use in medicine, and in the treatment of malaria in particular, to compositions containing them, to processes for their preparation and to intermediates used in such processes.