84906-81-0

Basic information

• Product Name: 2-HYDROXYQUINOLINE-4-CARBOXYLIC ACID
• Synonyms: IFLAB-BB F1918-0080;2-HYDROXYQUINOLINE-4-CARBOXYLIC ACID;1,2-DIHYDRO-2-OXOQUINOLINE-4-CARBOXYLIC ACID;AKOS AUF0188;RARECHEM AQ NN 0221;4-Quinolinecarboxylicacid,2-hydroxy-(9CI);4-Carboxy-2-hydroxyquinoline
• CAS NO: 84906-81-0
• Molecular Formula: C10H7NO3
• Molecular Weight: 189.17
• EINECS: 1312995-182-4
• Product Categories: QUINOLINE;Aromatic Cinnamic Acids, Esters and Derivatives;Quinoline&Isoquinoline;Building Blocks;Heterocyclic Building Blocks;Quinolines
• Mol File: 84906-81-0.mol

Chemical Properties

• Melting Point: >300 °C
• Boiling Point: 403.6°C at 760 mmHg
• Flash Point: 197.9°C
• Appearance: /
• Density: 1.480±0.06 g/cm3(Predicted)
• Vapor Pressure: 3.07E-07mmHg at 25°C
• Storage Temp.: 2-8°C
• PKA: 2.69±0.10(Predicted)
• CAS DataBase Reference: 2-HYDROXYQUINOLINE-4-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 2-HYDROXYQUINOLINE-4-CARBOXYLIC ACID(84906-81-0)
• EPA Substance Registry System: 2-HYDROXYQUINOLINE-4-CARBOXYLIC ACID(84906-81-0)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Safety Statements: S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.; S36:Wear suitable prot
• WGK Germany: 3
• Hazardous Substances Data: 84906-81-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
2-Hydroxyquinoline-4-carboxylic acid is used as a key intermediate in the synthesis of various pharmaceuticals and organic compounds. Its unique structure allows for the development of new drugs with potential therapeutic benefits.
Used in Disease Treatment:
In the field of medicine, 2-Hydroxyquinoline-4-carboxylic acid is used as a potential therapeutic agent for the treatment of various diseases, including tuberculosis and cancer. Its ability to target specific biological pathways makes it a promising candidate for further research and development.
Used in Antimicrobial Applications:
2-Hydroxyquinoline-4-carboxylic acid is used as an antimicrobial agent due to its ability to inhibit the growth of certain microorganisms. This property can be harnessed in the development of new antimicrobial drugs and treatments.
Used in Antioxidant Formulations:
The antioxidant properties of 2-Hydroxyquinoline-4-carboxylic acid make it a valuable component in antioxidant formulations. It can be used to protect cells from oxidative damage and may have potential applications in the prevention and treatment of oxidative stress-related diseases.
Used in Organic Chemistry Research:
As an important reagent in organic chemistry, 2-Hydroxyquinoline-4-carboxylic acid is used in various research applications to explore its chemical properties and potential reactions. This contributes to the advancement of organic chemistry and the discovery of new compounds and applications.

InChI:InChI=1/C10H7NO3/c12-9-5-7(10(13)14)6-3-1-2-4-8(6)11-9/h1-5H,(H,11,12)(H,13,14)/p-1

Upstream product

• 491-35-0 C₆H₄NCH₂CHCCH₂ 
• 574-17-4 1-acetyl-1H-indole-2,3-dione 
• 5467-57-2 2-chloroquinoline-4-carboxylic acid 
• 5467-61-8 ethyl ester of 2-chlorocinchoninic acid 
• 910035-64-2 ethyl (2Z)-(2-oxo-1,2-dihydro-3H-indol-3-ylidene)acetate 
• 32375-61-4 2-(2-acetamidophenyl)-2-oxoacetic acid 
• 91-56-5 indole-2,3-dione 
• 64-19-7 acetic acid 
• 486-74-8 4-quinolinic acid 
• 7647-01-0 hydrogenchloride 
• 65112-88-1 ethyl oxindole-3-glyoxalate 
• 118-10-5 Cinchonin 
• 42366-35-8 hydroxyimino-N-phenylacetamide 
• 607-66-9 4-methylquinolin-2-ol 

Downstream Products

• 107520-08-1 2-hydroxy-4-quinoline 
• 14179-84-1 2-oxo-1,2,3,4-tetrahydroquinoline-4-carboxylic acid 
• 80947-25-7 2-chloroquinoline-4-amine 
• 87864-14-0 2-chloro-quinoline-4-carboxylic acid-(2-diethylamino-ethylamide) 
• 106473-25-0 3-[4]quinolyl-3-oxo-propionic acid ethyl ester 

Relevant articles and documents

Quinoline carboxamide core moiety-based compounds inhibit P. falciparum falcipain-2: Design, synthesis and antimalarial efficacy studies

Targeting Falcipain-2 (FP2) for the development of antimalarials is a promising and established concept in antimalarial drug discovery and development. FP2, a member of papain-family cysteine protease of the malaria parasite Plasmodium falciparum holds an important role in hemoglobin degradation pathway. A new series of quinoline carboxamide-based compounds was designed, synthesized and evaluated for antimalarial activity. We integrated molecular hybridization strategy with in-silico drug design to develop FP2 inhibitors. In-vitro results of FP2 inhibition by Qs17, Qs18, Qs20 and Qs21 were found to be in low micromolar range with IC50 4.78, 7.37, 2.14 and 2.64 μM, respectively. Among the 25 synthesized compounds, four compounds showed significant antimalarial activities. These compounds also depicted morphological and food-vacuole abnormalities much better than that of E-64, an established FP2 inhibitor. Overall these aromatic substituted quinoline carboxamides can serve as promising leads for the development of novel antimalarial agents.

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.

Preparation method of 2-hydroxy-4-carboxylquinoline

The invention belongs to the technical field of chemical synthesis and in particular relates to a production preparation method of a dibucaine hydrochloride intermediate 2-hydroxy-4-carboxylquinoline.The method comprises the following steps: (1) putting glacial acetic acid into a reaction kettle; while stirring, adding isatin, malonic acid and sodium acetate; (2) heating the solution in step (1)and raising the temperature until the solution is reflowed; after reflowing, cooling to room temperature; (3) decompressing and evaporating materials in step (2) to remove the glacial acetic acid (which is recycled); (4) adding de-ionized water into the materials which are subjected to evaporation to remove the glacial acetic acid in step (3), and stirring and crystallizing; after finishing crystallization, spinning and filtering; eluting with the glacial acetic acid and then eluting with methanol; drying a wet product to obtain the 2-hydroxy-4-carboxylquinoline. The synthesis method providedby the invention adopts a one-spoon stewing technology to obtain a target product, so that the operation is simplified, the production period is shortened and the production cost is reduced; the obtained product has high purity and high yield and is suitable for large-scale production.

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.

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.

Synthesis and anti-tuberculosis activity of 2,4-disubstituted quinolines

Synthesis and anti-tuberculosis activity of a new series of 2,4-disubstituted quinolines have been reported. The most promising compounds have been found to exhibit 99% inhibition at 6.25 ng/mL against drug-sensitive M. tuberculosis H37Rv strain and >90% inhibition at 12.5 ng/mL against isoniazid resistant TB strain.

Microwave-assisted synthesis of quinoline derivatives from isatin

Microwave irradiation has been used for a rapid and efficient synthesis of quinoline-4-carboxylic acids 5a-g and 1,2,3,4-tetrahydroacridine-9-carboxylic acid (6) from the reaction of isatins 1-3 with acyclic and cyclic ketones in basic medium. 2-Hydroxyquinoline-4-carboxylic acid (11) was also obtained by irradiating a mixture of isatin 1 and malonic acid in AcOH. The esters of 5f and 11 and their respective hydrazides 8 and 13 were also prepared under MWI. Copyright Taylor & Francis, Inc.