Nitroxoline

Base Information

• Chemical Name: Nitroxoline
• CAS No.: 4008-48-4
• Molecular Formula: C9H6N2O3
• Molecular Weight: 190.158
• Hs Code.: 29334900
• European Community (EC) Number: 223-662-4
• NSC Number: 760393,74947
• UNII: A8M33244M6
• DSSTox Substance ID: DTXSID4046284
• Nikkaji Number: J3.716H
• Wikipedia: Nitroxoline
• Wikidata: Q304570
• NCI Thesaurus Code: C72634
• Pharos Ligand ID: QJHCLT7QDGF4
• Metabolomics Workbench ID: 43551
• ChEMBL ID: CHEMBL1454910
• Mol file: 4008-48-4.mol

Synonyms:5-nitro-8-hydroxyquinoline;5-nitroquinolin-8-ol;5-nitrox;5-NOK;Cysto-saar plus;Nibiol;nitroxoline;nitroxoline monofluoride;nitroxoline, potassium salt

Chemical Property of Nitroxoline

Chemical Property:

• Appearance/Colour: ochre-yellow to brownish crystalline powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 181-183 °C(lit.)
• Refractive Index: 1.728
• Boiling Point: 419 °C at 760 mmHg
• PKA: 2.55±0.10(Predicted)
• Flash Point: 207.2 °C
• PSA: 78.94000
• Density: 1.496 g/cm³
• LogP: 2.37180
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility.: alcohol: very slightly soluble
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 190.03784206
• Heavy Atom Count: 14
• Complexity: 229

Purity/Quality:

99% ^*data from raw suppliers

5-Nitro-8-hydroxyquinoline ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T, Xi, Xn
• Hazard Codes: T,Xi,Xn
• Statements: 23/24/25-36/37/38-22/24/25-20/21/22
• Safety Statements: 26-36-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(C=CC(=C2N=C1)O)[N+](=O)[O-]
• General Description: Nitroxoline is a 5-nitro-8-hydroxyquinoline derivative that has been investigated for its potential as a cathepsin B inhibitor, particularly in the context of cancer therapy. While structural modifications of nitroxoline have not significantly enhanced its in vitro inhibitory activity against cathepsin B compared to earlier findings, certain derivatives demonstrate promising anti-tumor effects by reducing collagen degradation and inhibiting tumor cell invasion. This suggests its potential utility in developing non-peptidic anti-cancer agents targeting cathepsin B-mediated pathways.

Technology Process of Nitroxoline

There total 11 articles about Nitroxoline 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: 90.1%

5-Nitroso-8-hydroxyquinoline hydrochloride (63450-86-2) → nitroxoline (4008-48-4)

Guidance literature:

With nitric acid; In water; at 17 ℃; for 1.41667h; Inert atmosphere; Cooling with ice;

DOI:10.13005/ojc/310144

Reference yield: 80.0%

8-quinolinol (148-24-3,24804-14-6) → nitroxoline (4008-48-4)

Guidance literature:

8-quinolinol; With sulfuric acid; sodium nitrite; In water; at 15 - 18 ℃;

With nitric acid; In water; at 20 ℃;

DOI:10.1021/cn500119g

Reference yield:

5-nitroso-8-hydroxyquinoline (3565-26-2) → nitroxoline (4008-48-4)

Guidance literature:

With water; nitric acid;

DOI:10.1039/jr9540000570

upstream raw materials:

5-nitroso-8-hydroxyquinoline

8-ethoxy-5-nitroquinoline

glycerol

2-hydroxy-5-nitroaniline

Downstream raw materials:

7-diethylaminomethyl-5-nitro-quinolin-8-ol

7-bromo-8-hydroxy-5-nitroquinoline

5-nitro-7-(pyrrolidin-1-ylmethyl)quinolin-8-ol

5-nitro-7-(piperidin-1-ylmethyl)quinolin-8-ol

Refernces

Cathepsin B inhibitors: Further exploration of the nitroxoline core

10.1016/j.bmcl.2018.02.042

The research focuses on the design and synthesis of novel derivatives of nitroxoline as inhibitors of human cathepsin B, a cysteine protease implicated in various pathological processes, including cancer. The study aims to further define the structural requirements for cathepsin B inhibition by nitroxoline derivatives and to provide knowledge that could lead to the development of non-peptidic compounds useful against tumor progression. The researchers synthesized over 60 nitroxoline-based derivatives and evaluated their ability to inhibit both endopeptidase and exopeptidase activities of cathepsin B. They also assessed the compounds' ability to reduce extracellular and intracellular collagen IV degradation and their impact on tumor cell invasion in vitro. The study concluded that while significant improvement in in vitro cathepsin B inhibition was not achieved compared to previous results, several derivatives showed promising efficacy in tumor-cell-based assays. Key chemicals used in the synthesis process included various nitroxoline derivatives, amidoacetonitriles, aminoacetonitriles, and different substituents at positions 2, 7, and 8 of the nitroxoline core, as well as reagents for coupling reactions and nitration procedures.

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