10470-83-4Relevant academic research and scientific papers
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.
Efficient synthesis of substituted quinoline-5,8-quinones from 8-hydroxyquinolines by photooxygenation
Cossy, Janine,Belotti, Damien
, p. 4329 - 4331 (2001)
Substituted quinoline-5,8-quinones were obtained in good yield by photooxygenation of substituted 8-hydroxyquinolines.
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.
Reaction of 2,5-dimethylpyrroles with quinones. Synthesis of new pyrrolylquinones dyes
Lion, Claude,Baudry, Richard,Hedayatullah, Mir,Da Conceicao, Louis,Genard, Sylvie,Maignan, Jean
, p. 125 - 130 (2002)
The reaction of 1,4-naphthoquinone (1) with 2,5-dimethylpyrroles (7a-7d) gives only 3-(1,4-naphthoquinonyl)-2,5-dimethylpyrroles. Extending the reaction to other quinones: 5-hydroxy-1,4-naphthoquinone (2), 1,2-naphthoquinone (3), quinoline-5,8-dione (4) and quinoxaline-5,8-dione (5), of which nothing was known, allows the synthesis of new pyrrolylquinones.
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.
Probing the TiO2 photocatalytic mechanisms in water purification by use of quinoline, photo-fenton generated OH. radicals and superoxide dismutase
Cermenati, Laura,Pichat, Pierre,Guillard, Chantal,Albini, Angelo
, p. 2650 - 2658 (1997)
In an attempt to improve our understanding of the basic mechanisms of the degradation of aromatic pollutants in water by TiO2 photocatalysis, quinoline (benzo[b]pyridine) was selected as a molecular probe, principally because of the difference in electron density over its two rings. This study was based on the identification and quantification of the primary products or principal secondary products of quinoline degradation either by TiO2 photocatalysis at pH 3 and 6 or by OH. radicals generated via the photo-Fenton reaction (Fe(II/III)-H2O2-UV) at pH 3. In this latter case, the three major products were those expected from the preferential electrophilic attack of OH. radicals on the electron-richer benzene moiety, viz., 5-, and 8-hydroxyquinolines and quinoline-5,8-dione derived from them. TiO2 photocatalysis did not yield this dione, and at the same percentages of degraded quinoline, the amounts of 5-hydroxyquinoline were lower by a factor of ca. 2 at pH 3 and ca. 10 at pH 6 (those of the 8-isomer were also decreased but no accurate measurements were obtained). In addition, at pH 6, we observed marked increases in the amounts of products corresponding to the oxidation of the pyridine moiety, viz., 4-quinolinone and especially 2-aminobenzaldehyde (the major product) and its N-formyl derivative. These results show that oxidative steps in TiO2 photocatalysis do not involve only OH. radicals. It was also observed that, at pH 6, superoxide dismutase (SOD), which catalyzes the elimination of O2.- species, decreased the TiO2 photocatalytic rate of quinoline disappearance, almost suppressed the formation of 2-aminobenzaldehyde, and lowered the amount of 4-quinolinone. The SOD and pH effects suggest a mechanism involving quinoline activation by hole transfer, followed by superoxide addition to the resulting radical cation. The nucleophilic character of superoxide implies addition to the pyridine moiety, i.e., with a regioselectivity opposite that of the OH. radical pathway.
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.
Use of a readily removable auxiliary group for the synthesis of pyrrolidones by the palladium-catalyzed intramolecular amination of unactivated γ C(sp3)-H Bonds
He, Gang,Zhang, Shu-Yu,Nack, William A.,Li, Qiong,Chen, Gong
, p. 11124 - 11128 (2013)
Easy on, easy off: Directing groups found to promote the palladium-catalyzed amination of γ C(sp3)-H and C(sp 2)-H bonds of secondary amides included 5-methoxy-8-aminoquinoline, which can be removed under mild conditions (see scheme; CAN=ceric ammonium nitrate). In conjunction with a β-C-H methylation or γ-C-H arylation step, the γ-C(sp3)-H amination provided access to complex pyrrolidones from readily available precursors. Copyright
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.
Development of novel amino-quinoline-5,8-dione derivatives as NAD(P)H:quinone oxidoreductase 1 (NQO1) inhibitors with potent antiproliferative activities
Ling, Yong,Yang, Qiu-Xing,Teng, Yu-Ning,Chen, Shi,Gao, Wei-Jie,Guo, Jing,Hsu, Pei-Ling,Liu, Yue,Morris-Natschke, Susan L.,Hung, Chin-Chuan,Lee, Kuo-Hsiung
, p. 199 - 209 (2018)
Fourteen novel amino-quinoline-5,8-dione derivatives (6a-h and 7a-h) were designed and synthesized by coupling different alkyl- or aryl-amino fragments at the C6- or C7-position of quinoline-5,8-dione. All target compounds showed antiproliferative potency in the low micromolar range in both drug sensitive HeLaS3 and multidrug resistant KB-vin cell lines. Compounds 6h, 6d, 7a, and 7d exhibited more potent antiproliferative effects than the other compounds. Especially, compounds 6d and 7d displayed NQO1-dependent cytotoxicity and competitive NQO1 inhibitory effects in both drug sensitive HeLaS3 and multidrug resistant KB-vin cell lines. Furthermore, compounds 6h, 6d, 7a, and 7d induced a dose-dependent lethal mitochondrial dysfunction in both drug sensitive HeLaS3 and multidrug resistant KB-vin cells by increasing intracellular reactive oxygen species (ROS) levels. Notably, compound 7d selectively inhibited cancer cells, but not non-tumor liver cell proliferation in vitro, and significantly triggered HeLaS3 cell apoptosis by regulating apoptotic proteins of Bcl-2, Bax, and cleaved caspase-3 in a dose-dependent manner. Our findings suggest that these novel C6- or C7-substituted amino-quinoline-5,8-dione derivatives, such as 7d, could be further developed in the future as potent and selective antitumor agents to potentially circumvent multi-drug resistance (MDR).
