10470-83-4Relevant articles and documents
Oxidation of phenols to quinones by bis(trifluoroacetoxy)iodobenzene
Barret,Daudon
, p. 4871 - 4872 (1990)
Bis (trifluoroacetoxy) iodobenzene oxidizes phenols into quinones in good yield.
G-quadruplex and duplex DNA binding studies of novel Ruthenium(II) complexes containing ascididemin ligands
Wumaier, Maierhaba,Shi, Jing-Jing,Yao, Tian-Ming,Hu, Xiao-Chun,Gao, Ru-Ru,Shi, Shuo
, (2019)
In this paper, three new Ruthenium(II) polypyridyl complexes containing ascididemin (ASC) as main ligand have been synthesized and characterized. Their interactions with different G-quadruplex (Htelo, c-myc and c-kit) (Htelo: human telomeric DNA, c-myc: cellular-myelocytomatosis viral oncogene, c-kit: oncogene c-kit promoter sequences) and duplex (ds26) DNA sequences were comparatively studied with the free ligand ASC by a series of spectroscopic techniques including UV–vis (ultraviolet-visible) spectroscopy, FID (fluorescent intercalator displacement) assay, and FRET (fluorescence resonance energy transfer) melting assay. Molecular docking studies were also performed to support the binding mode of the compounds with G-quadruplex DNA. Results indicated that [Ru(bpy)2ASC]·(PF6)2 (1), [Ru(phen)2ASC]·(PF6)2 (2), [Ru(tatp)2ASC]·(PF6)2 (3) (bpy = 2,2′?bipyridine, phen = 1,10?phenanthroline, tatp = 1,4,8,9?tetra?aza?triphenylene) and ASC can effectively bind G-quadruplex and duplex DNA and stabilization ability lies in the order 3 > 2 > 1 > ASC. Complex 3 was determined to be the most promising candidate for further in vitro studies and potential anticancer drug.
Synthesis and biological evaluation of novel isothiazoloquinoline quinone analogues
Chen, Ling,Gao, Jin-Lei,Hao, Ying,Kong, Fan-Rong,Liu, Hong-Dou,Liu, Li-Jun,Liu, Su-You,Luo, Zhi-Yong,Ma, Da-You,Wang, Liu-Liu,Xie, Yuan-Zhu,Zou, Zi-Zheng
, (2020)
Natural quinones and their analogues have attracted growing attention because of their novel anticancer activities. A series of novel isothiazoloquinoline quinone analogues were synthesized and evaluated for antitumor activities against four different kind of cancer cells. Among them, isothiazoloquinolinoquinones inhibited cancer cells proliferation effectively with IC50 values in the nanomolar range, and isothiazoloquinolinoquinone 13a induced the cell apoptosis. Further exploration of possible mechanism of action indicates that 13a not only activates ROS production through NQO1-directed redox cycling but also inhibits the phosphorylation of STAT3. These findings indicate that 13a has potential use for the development of new skeleton drug candidate as an efficient substrate of NQO1 and STAT3 inhibitor.
A new synthesis of quinoline-5,8-quinone
Amarasekara, Ananda S.
, p. 3063 - 3066 (1999)
Sensitised photo-oxidations of 8-hydroxy quinoline (1) or 5-hydroxy quinoline (2) gives quinoline-5,8-quinone (3) in 64-70% yield.
The aza-analogues of 1,4-naphthoquinones are potent substrates and inhibitors of plasmodial thioredoxin and glutathione reductases and of human erythrocyte glutathione reductase
Morin, Christophe,Besset, Tatiana,Moutet, Jean-Claude,Fayolle, Martine,Brueckner, Margit,Limosin, Daniele,Becker, Katja,Davioud-Charvet, Elisabeth
, p. 2731 - 2742 (2008)
Various aza-analogues of 1,4-naphthoquinone and menadione were prepared and tested as inhibitors and substrates of the plasmodial thioredoxin and glutathione reductases as well as the human glutathione reductase. The replacement of one to two carbons at the phenyl ring of the 1,4-naphthoquinone core by one to two nitrogen atoms led to an increased oxidant character of the molecules in accordance with both the redox potential values and the substrate efficiencies. Compared to the 1,4-naphthoquinone and menadione, the quinoline-5,8-dione 1 and both quinoxaline-5,8-diones 5 and 6 behaved as the most efficient subversive substrates of the three NADPH-dependent disulfide reductases tested. Modulation of these parameters was observed by alkylation of the aza-naphthoquinone core. The Royal Society of Chemistry.
An efficient method for the synthesis of 6, 7-bis(alkylthio- or alkylamino-substituted)quinoline-5, 8-diones via nucleophilic addition/oxidation of alkylthio and alkylamino derivatives to quinoline-5, 8-dione
Odens, Herman H.,Silva, Trevor S.,Olusola, Candace N.,Odens, Herman H.,Howe, Victoria A.,Wijatyk, Anna I.
, p. 54 - 63 (2021/12/01)
A new variety of 6, 7-bis(alkylthio- or alkylamino-substituted)quinoline-5, 8-diones were prepared by the addition of mercaptans or amino nucleophiles to quinoline-5, 8-dione after subsequent oxidation with NaIO4. The core quinoline-5, 8-dione intermediate was prepared from the oxidation of 5-quinolinol or 8-quinolinol by [bis(trifluoroacetoxy)iodo]benzene, PIFA, in the presence of water and acetonitrile as solvents. No good leaving groups were utilized to insert the alkylthio or alkylamino groups into the quinoline ring. The synthesized compounds will be tested for their anti-inflammatory, anti-bacterial and tuberculostatic inhibition activities at a later stage.{figure presented}.
Selective Removal of Aminoquinoline Auxiliary by IBX Oxidation
Zhang, Zhiguo,Li, Xiang,Song, Mengmeng,Wan, Yameng,Zheng, Dan,Zhang, Guisheng,Chen, Gong
, p. 12792 - 12799 (2019/07/03)
8-Aminoquinoline (AQ) is a widely used bidentate auxiliary in metal-catalyzed directed C-H functionalization reactions. Herein, we report an efficient and chemoselective method to convert various N-quinolyl carboxamides to primary amides with the treatment of a stoichiometric amount of 2-iodoxybenzoic acid oxidant or the combination of a catalytic amount of 2-iodobenzoic acid and Oxone co-oxidant in mixed solvents of H2O and HFIP. Its unique compatibility with the Phth-protected α-amino acid (αAA) substrates enhances the overall synthetic utility of the AQ-directed palladium-catalyzed C-H functionalization strategy for synthesis of complex αAAs.
