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-]
• Description: Nitroxoline is an 8-hydroxyquinoline that has diverse biological activities, including antibacterial, antiproliferative, and bromodomain interaction-inhibiting properties. Nitroxoline is active against the bacteria E. coli, S. aureus, E. faecalis, K. pneumoniae, and P. mirabilis in vitro (MIC90s = 4, 4, 8, 8, and 8 mg/L, respectively). It also inhibits biofilm formation of certain strains of multidrug-resistant (MDR) A. baumannii and P. aeruginosa, as well as methicillin-resistant S. aureus (MRSA) and S. epidermidis (MRSE) with minimum biofilm eradication concentration (MBEC) values of 46.9, 1,500, 188, and 125 μM, respectively. Nitroxoline inhibits the growth of human U87 and U251 glioma, A549 lung, and PC3 prostate cancer cells (IC50s = 50, 6, 38, and 23 μg/ml, respectively). In vivo, it reduces tumor growth in a PTEN- and KRAS-driven glioma mouse model when administered at a dose of 80 mg/kg per day. Nitroxoline also inhibits the interaction between the first bromodomain of bromodomain-containing protein 4 (BRD4) with acetylated histone H4 with an IC50 value of 0.98 μM.
• Uses: antibacterial 5-Nitro-8-hydroxyquinoline is an antimicrobial agent used for the treatment of urinary tract infection. 5-Nitro-8-hydroxyquinoline is also a potent and reversible inhibitor of cathepsin B. 5-Nitro-8-h ydroxyquinoline has been shown to have anti-cancer activity. 8-Hydroxy-5-nitroquinoline was used in the synthesis of novel CO2-soluble 8-hydroxyquinoline chelating agents.

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-(morpholinomethyl)-5-nitroquinolin-8-ol

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

7-bromo-8-hydroxy-5-nitroquinoline

C₁₅H₉IN₂O₃

Refernces

• 1、 Yatsenko,Paseshnichenko,Chernyshev,Schenk. "Powder diffraction study of the hydrogen bonds in nitroxoline and its hydrochloride.". . p. o19-21. Retrieved 2002.
• 2、 Oni, Timothy Toba,Okoro, Uchechukwu Chris,Ugwu, David Izuchukwu. "Synthesis of 1-azabenzo[a]phenoxazin-5-one and 11-amino-1,8,10-triazabenzo[a]phenoxazin-5-one and their Functionalized aryl derivatives via Mizoroki-Heck arylation methodology". . p. 371 - 378. Retrieved 2015.
• 3、 Jianbo, He,Tingting, Zhou,Yongjing, Cao,Yuanyuan, Zhang,Weiqing, Yang,Menglin, Ma. "Study on Relationship Between Fluorescence Properties and Structure of Substituted 8-Hydroxyquinoline Zinc Complexes". . p. 1121 - 1126. Retrieved 2018/08/17.