Quinoline-4-carboxylic acid

Base Information

• Chemical Name: Quinoline-4-carboxylic acid
• CAS No.: 486-74-8
• Molecular Formula: C10H7NO2
• Molecular Weight: 173.171
• Hs Code.: 29334900
• European Community (EC) Number: 207-640-1
• NSC Number: 13138
• UNII: W6V42SQ9E8
• DSSTox Substance ID: DTXSID20197567
• Nikkaji Number: J6.015A
• Wikidata: Q27102986
• Metabolomics Workbench ID: 49845
• ChEMBL ID: CHEMBL4435617
• Mol file: 486-74-8.mol

Synonyms:4-quinolinecarboxylic acid;cinchoninic acid;quinoline-4-carboxylic acid

Chemical Property of Quinoline-4-carboxylic acid

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 1.85E-05mmHg at 25°C
• Melting Point: 254-255 °C(lit.)
• Boiling Point: 348.7 °C at 760 mmHg
• PKA: 1.03±0.10(Predicted)
• Flash Point: 164.7 °C
• PSA: 50.19000
• Density: 1.339 g/cm³
• LogP: 1.93300
• Storage Temp.: 2-8°C
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 173.047678466
• Heavy Atom Count: 13
• Complexity: 205

Purity/Quality:

98% ^*data from raw suppliers

Quinoline-4-carboxylicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38-36/38
• Safety Statements: 26-36-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Quinolines
• Canonical SMILES: C1=CC=C2C(=C1)C(=CC=N2)C(=O)O
• General Description: Quinoline-4-carboxylic acid derivatives, such as those synthesized from phenolic aldehydes, exhibit potent inhibitory activity against human dihydroorotate dehydrogenase (hDHODH), a key enzyme in pyrimidine biosynthesis, making them promising candidates for anticancer therapy. These compounds demonstrate significant cytotoxicity against cancer cell lines (MCF-7, A549, A375) while showing selectivity over normal cells (HaCaT), suggesting their potential as chemotherapeutic agents. Their lipophilicity and molecular docking studies further highlight structural features that enhance hDHODH inhibition, supporting their development as targeted anticancer drugs.

Technology Process of Quinoline-4-carboxylic acid

There total 90 articles about Quinoline-4-carboxylic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

quinoline-4-carboxaldehyde (4363-93-3) → 4-quinolinic acid (486-74-8)

Guidance literature:

With formic acid; dihydrogen peroxide; at 0 - 4 ℃; for 12h;

DOI:10.1055/s-1993-25851

Reference yield: 89.0%

quinoline-2,4-dicarboxylic acid (5323-57-9) → 4-quinolinic acid (486-74-8)

Guidance literature:

In diphenylether; at 200 - 215 ℃; for 0.25h;

DOI:10.1016/0223-5234(92)90032-V

Reference yield: 87.0%

C6H4NCH2CHCCH2 (491-35-0) → 4-quinolinic acid (486-74-8)

Guidance literature:

With N-hydroxyphthalimide; air; Nitrogen dioxide; cobalt(II) acetate; manganese(II) acetate; In acetic acid; at 150 ℃; for 5h; under 15201 Torr;

DOI:10.1039/b108880g

upstream raw materials:

cinchonan-9-one

isopentyl nitrite

1-quinolin-4-yl-3-(vinyl-piperidin-4-yl)-propan-1-one

sodium ethanolate

Downstream raw materials:

quinoline-4-carboxylic acid methyl ester

ethyl quinoline-4-carboxylate

4-methoxycarbonyl-1-methyl-quinolinium; iodide

(RS)-1,2,3,4-tetrahydroquinoline-4-carboxylic acid

Refernces

Potent human dihydroorotate dehydrogenase inhibitory activity of new quinoline-4-carboxylic acids derived from phenolic aldehydes: Synthesis, cytotoxicity, lipophilicity and molecular docking studies

10.1016/j.bioorg.2020.104373

The study focuses on the synthesis and evaluation of a series of novel 2-substituted quinoline-4-carboxylic acids derived from phenolic aldehydes, which were designed to target human dihydroorotate dehydrogenase (hDHODH), an enzyme crucial for cancer cell proliferation. These compounds were tested for their inhibitory activity against hDHODH, cytotoxicity against cancer cell lines (MCF-7, A549, A375), and a normal cell line (HaCaT), as well as their lipophilicity. The purpose of these chemicals was to serve as potential chemotherapeutic agents, with the aim of developing new drugs that can inhibit hDHODH, thereby disrupting pyrimidine biosynthesis and hindering cancer cell growth. The study also included molecular docking studies to understand the structural differences that contribute to the varying levels of activity among the synthesized compounds.

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