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Merck

140325

Sigma-Aldrich

8-Hydroxy-5-nitrochinolin

96%

Synonym(e):

5-Nitro-8-chinolinol

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About This Item

Empirische Formel (Hill-System):
C9H6N2O3
CAS-Nummer:
Molekulargewicht:
190.16
EG-Nummer:
MDL-Nummer:
UNSPSC-Code:
12352100
PubChem Substanz-ID:
NACRES:
NA.22

Qualitätsniveau

Assay

96%

Form

powder

mp (Schmelzpunkt)

181-183 °C (lit.)

Löslichkeit

alcohol: very slightly soluble
diethyl ether: very slightly soluble
hydrochloric acid: freely soluble (hot)

Funktionelle Gruppe

nitro

SMILES String

Oc1ccc([N+]([O-])=O)c2cccnc12

InChI

1S/C9H6N2O3/c12-8-4-3-7(11(13)14)6-2-1-5-10-9(6)8/h1-5,12H

InChIKey

RJIWZDNTCBHXAL-UHFFFAOYSA-N

Anwendung

8-Hydroxy-5-nitroquinoline was used in the synthesis of novel CO2-soluble 8-hydroxyquinoline chelating agents.

Biochem./physiol. Wirkung

8-Hydroxy-5-nitroquinoline is an effective anti-microbial and anti-cancer agent. It is an effective drug for the treatment of urinary tract infections due to gram negative bacilli.

Piktogramme

Skull and crossbones

Signalwort

Danger

Gefahreneinstufungen

Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Zielorgane

Respiratory system

Lagerklassenschlüssel

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges


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A V Yatsenko et al.
Acta crystallographica. Section C, Crystal structure communications, 58(Pt 1), o19-o21 (2002-01-10)
The crystal structures of 8-hydroxy-5-nitroquinoline, C9H6N2O3, (I), and 8-hydroxy-5-nitroquinolinium chloride, C9H7N2O3+*Cl-, (II), have been determined from X-ray powder data. In (I), the molecules are linked via moderately strong hydrogen bonds to form dimers. Such a packing motif is likely to
C Pelletier et al.
Antimicrobial agents and chemotherapy, 39(3), 707-713 (1995-03-01)
The antibacterial activity of nitroxoline (NIT), an antibiotic used in the treatment of acute or recurrent urinary tract infections caused by Escherichia coli, is decreased in the presence of Mg2+ and Mn2+ but not Ca2+. In order to elucidate the
Gau-Yi Gao et al.
Journal of pharmaceutical sciences, 99(1), 255-261 (2009-06-17)
To investigate the physicochemical characteristics, thermodynamics, possible sublimation process and kinetics of nitroxoline, differential scanning calorimetry (DSC), isothermal thermogravimetry (TG), and Fourier transform infrared (FTIR) microspectroscopy equipped with a micro hot-stage of DSC microscopy assembly (simultaneous DSC-FTIR method) were used.
Mohamed M Ghoneim et al.
Bioelectrochemistry (Amsterdam, Netherlands), 80(2), 162-168 (2010-09-14)
Nitroxoline has been reduced at the mercury electrode in buffered solutions (pH 2-11) in two irreversible cathodic steps. The first step was attributed to reduction of -NO(2) group to the hydroxylamine stage and the second one to reduction-saturation of the
Joong Sup Shim et al.
Journal of the National Cancer Institute, 102(24), 1855-1873 (2010-11-20)
Angiogenesis plays an important role in tumor growth and metastasis; therefore, inhibition of angiogenesis is a promising strategy for developing new anticancer drugs. Type 2 methionine aminopeptidase (MetAP2) protein is likely a molecular target of angiogenesis inhibitors. Nitroxoline, an antibiotic

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