29366-44-7Relevant articles and documents
Synthesis and structure elucidation of oxidative coupling products of 2-hydroxy-1,4-naphthoquinones
Yakubovskaya,Kochergina,Denisenko,Berdyshev,Glazunov,Anufriev
, p. 301 - 305 (2006)
2,3-Dihydro-3-O-(1,4-naphthoquinon-2-yl)-2-oxo-1,4-naphthoquinones are the products of oxidative coupling of substituted 2-hydroxy-1,4-naphthoquinones (regardless of the presence of peri-hydroxy groups in their structures) under the action of lead dioxide
Tridentate 3-Substituted Naphthoquinone Ruthenium Arene Complexes: Synthesis, Characterization, Aqueous Behavior, and Theoretical and Biological Studies
Geisler, Heiko,Westermayr, Julia,Cseh, Klaudia,Wenisch, Dominik,Fuchs, Valentin,Harringer, Sophia,Plutzar, Sarah,Gajic, Natalie,Hejl, Michaela,Jakupec, Michael A.,Marquetand, Philipp,Kandioller, Wolfgang
, p. 9805 - 9819 (2021/06/30)
A series of nine RuII arene complexes bearing tridentate naphthoquinone-based N,O,O-ligands was synthesized and characterized. Aqueous stability and their hydrolysis mechanism were investigated via UV/vis photometry, HPLC-MS, and density functional theory calculations. Substituents with a positive inductive effect improved their stability at physiological pH (7.4) intensely, whereas substituents such as halogens accelerated hydrolysis and formation of dimeric pyrazolate and hydroxido bridged dimers. The observed cytotoxic profile is unusual, as complexes exhibited much higher cytotoxicity in SW480 colon cancer cells than in the broadly chemo- (incl. platinum-) sensitive CH1/PA-1 teratocarcinoma cells. This activity pattern as well as reduced or slightly enhanced ROS generation and the lack of DNA interactions indicate a mode of action different from established or previously investigated classes of metallodrugs.
Organocatalytic Asymmetric Formal [3+2] Cycloaddition as a Versatile Platform to Access Methanobenzo[7]annulenes
Ramachary, Dhevalapally B.,Anif Pasha, Mohammed,Thirupathi, Guguloth
supporting information, p. 12930 - 12934 (2017/09/13)
Pharmaceutically and structurally important methanobenzo[7]annulenes were synthesized in very good yields with excellent enantio- and diastereoselectivities through an unprecedented organocatalytic formal [3+2] cycloaddition from readily available 2-alkyl-3-hydroxynaphthalene-1,4-diones and alkyl vinyl ketones.
Towards targeting anticancer drugs: Ruthenium(II)-arene complexes with biologically active naphthoquinone-derived ligand systems
Kubanik, Mario,Kandioller, Wolfgang,Kim, Kunwoo,Anderson, Robert F.,Klapproth, Erik,Jakupec, Michael A.,Roller, Alexander,S?hnel, Tilo,Keppler, Bernhard K.,Hartinger, Christian G.
, p. 13091 - 13103 (2016/09/04)
Anticancer active metal complexes with biologically active ligands have the potential to interact with more than one biological target, which could help to overcome acquired and/or intrinsic resistance of tumors to small molecule drugs. In this paper we present the preparation of 2-hydroxy-[1,4]-naphthoquinone-derived ligands and their coordination to a RuII(η6-p-cymene)Cl moiety. The synthesis of oxime derivatives resulted in the surprising formation of nitroso-naphthalene complexes, as confirmed by X-ray diffraction analysis. The compounds were shown to be stable in aqueous solution but reacted with glutathione and ascorbic acid rather than undergoing reduction. One-electron reduction with pulse radiolysis revealed different behavior for the naphthoquinone and nitroso-naphthalene complexes, which was also observed in in vitro anticancer assays.