1526-73-4Relevant articles and documents
SYNTHESIS AND BIOLOGICAL ACTIVITY OF 4-SUBSTITUTED 1,2-NAPHTHOQUINONES, 1,2-NAPHTHALENEDIOLS, AND THEIR DERIVATIVES
Grinev, A. N.,Arsenichev, I. K.,Nikolaeva, I. S.,Golovanova, L. A.,Pushkina, T. V.,et al.
, p. 411 - 417 (1985)
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Regiocontrolled synthesis and HIV inhibitory activity of unsymmetrical binaphthoquinone and trimeric naphthoquinone derivatives of conocurvone
Stagliano, Kenneth W.,Emadi, Ashkan,Lu, Zhenhai,Malinakova, Helena C.,Twenter, Barry,Yu, Min,Holland, Louis E.,Rom, Amanda M.,Harwood, John S.,Amin, Ronak,Johnson, Allison A.,Pommier, Yves
, p. 5651 - 5665 (2006)
Unsymmetrical biquinone and trimeric quinone derivatives were synthesized using halotriflate-biselectrophilic naphthoquinones through stepwise regioselective quinone substitution chemistry and evaluated for their ability to inhibit the cytopathogenic effects of HIV-1 using an MTT colorimetric assay. Compounds were also screened for their ability to inhibit the activity of HIV-1 integrase in vitro. Pyranylated trimeric quinones and biquinones exhibited both antiviral activity and integrase inhibitory activity. Conocurvone 1 and trimeric quinone 21 were the most potent HIV integrase inhibitors in the series. All of the biquinones showed HIV inhibitory activity. Simple methoxy substituted biquinones did not inhibit HIV-1 integrase.
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.
NAPTHOQUINONES, PRO-DRUGS, AND METHODS OF USE THEREOF
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Paragraph 00156, (2017/07/06)
Provided herein are naphthoquinones compounds such as those with a hydrogen bond donating group of the formula (I): wherein: R1, R2, R3, R4, R5, and n are as defined herein. Also provided herein are pharmaceutical composition of the present compounds and methods of treatment using the compounds including their use in the treatment of cancer.