Description
A quinoline derivative that displays mutagenic activity. It suppresses
luminescence of an indicator bacterium that is named Photobacterium
phosphoreum. This chemical forms two kinds of complexes with palladium
(II) and Gold (III). One kind is an ion-associated compound containing
hydrogen bond and hte other is the six membered metal chelates
containing metal-oxygen bonds.
Chemical Properties
Yellow Crystalline Solid
Uses
A quinoline derivative; shows mutagenic activity.
Definition
ChEBI: 8-hydroxyquinoline N-oxide is a quinoline N-oxide carrying a hydroxy substituent at position 8. It is a monohydroxyquinoline and a quinoline N-oxide. It is functionally related to a quinolin-8-ol. It is a conjugate acid of an 8-hydroxyquinoline N-oxide(1-).
General Description
8-Quinolinol
N-oxide is a toxicant which can suppress luminescence of an indicator bacterium
Photobacterium phosphoreum. It forms two types of complexes with gold(III) and palladium(II): type I are ion-associated compounds containing hydrogen bond and the other is the six-membered metal chelates containing metal-oxygen bonds.
Synthesis
8-hydroxyquinoline-N-oxide was synthesized from 8-hydroxyquinoline. A stirred solution of 8-hydroxyquinoline (25.00 g, 172.2 mmol) in 550 ml of CHCl
3 was cooled to 0° C., and 3 -chloroperoxybenzoic acid (40.00 g, 80% Tech. grade *0.231 mmol=0.185 mmol) was added slowly over 3 minutes. The solution was kept at 0° C. and stirred for 3 hours. During this period, the 3-chlorobenzoic acid byproduct precipitated. The 3-chlorobenzoic acid was removed by filtration and the orange filtrate was concentrated to dryness and the remaining solid was triturated with 2% NH40 H (2*200 ml). The solid was isolated on a frit and washed with H
2O.
References
[1] Naunyn-Schmiedeberg's Archives of Pharmacology, 1999, vol. 359, # 3, p. 168 - 177
[2] ChemCatChem, 2015, vol. 7, # 23, p. 3903 - 3910
[3] Patent: US2003/97000, 2003, A1
[4] Patent: US6617336, 2003, B1
[5] Organic Letters, 2011, vol. 13, # 14, p. 3556 - 3559
