- Synthesis of 1,4-Anthracene-9,10-dione derivatives and their regulation of nitric oxide, IL-1β and TNF-α in activated RAW264.7 cells
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Mitoxantrone is an anthracenedione antineoplastic and immunosuppressive agent approved for multiple sclerosis treatment. Novel mono- and disubstituted anthraquinone derivatives, analogues of mitoxantrone, were synthesized through the addition of lipophilic amino alcohols and evaluated for their effect on IL-1β, TNF-α and nitric oxide production by LPS/IFN-γ-stimulated RAW264.7 cells. The disubstituted 1,4-anthracene-9,10-dione 10 showed significant inhibition of nitric oxide, TNF-α and IL-1β production at the concentration of 5 μg/mL, with a much lower cytotoxicity than mitoxantrone. The monosubstituted 3, 4, 11, 12 and 13 also displayed a moderate to good inhibitory capacity on IL-1β production. However, the methylated compounds 11, 12 and 13 failed to inhibit the TNF-α production, and compound 13 was the only one to decrease the production of nitric oxide. None of these derivatives was toxic at the tested concentrations. Compounds 10 and 13 had better inhibitory capacity of the inflammatory mediators analyzed, with reliable viability of the cells.
- Correa, Tais Arthur,Alves, Caio C. S.,Castro, Sandra B. R.,Oliveira, Erick E.,Franco, Lucas S.,Ferreira, Ana P.,De Almeida, Mauro V.
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- A new kind of H-acid monoazo-anthraquinone reactive dyes with surprising colour
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A new kind of reactive dyes containing both monoazo and anthraquinone chromophores was obtained by using 1,4-bis((4-aminophenyl)amino)anthrancene- 9,10-dione as diazo component and 1-amino-8-naphthol-3,6-disulfonicacid (H-acid) derivatives as coupling components. The dyes were characterized by UV-Vis, IR, MS, 1H NMR and 13C NMR. The results showed that the maximum absorption wavelengths of the dyes were all about 590 nm, which indicated that they were a kind of blue dyes. 1H NMR and 13C NMR results revealed that there were two kinds of tautomerisms in dye structure and a new conjugated system formed between the anthraquinone ring and the phenyl azo linkage. Density functional theory (DFT) calculations also proved the formation of the new larger conjugated system from which the blue colour was generated. The fixations of the dyes on cotton were over 88% and the light fastness reached 5 grade.
- Shan, Bin,Tong, Xing,Xiong, Wei,Qiu, Wenzhu,Tang, Bingtao,Lu, Rongwen,Ma, Wei,Luo, Yi,Zhang, Shufen
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- A new InCl3-catalyzed reduction of anthrones and anthraquinones by using aluminum powder in aqueous media
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InCl3-catalyzed reduction of anthrones and anthraquinones was investigated under different conditions. A new synthetic method for anthracenes in aqueous media under mild conditions is described.
- Wang, Chunyan,Wan, Jieping,Zheng, Zhiguo,Pan, Yuanjiang
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p. 5071 - 5075
(2008/02/01)
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- Parimycin: Isolation and structure elucidation of a novel cytotoxic 2,3-dihydroquinizarin analogue of γ-indomycinone from a marine Streptomycete isolate
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In our screening of actinomycetes from the marine environment for bioactive components, a new antibiotic with a novel structure designated as parimycin was obtained from the culture broth of Streptomyces sp. isolate B8652. The structure of the new antibiotic was determined by spectroscopic methods and by comparison of the NMR data with those of the structurally related γ-indomycinone.
- Maskey, Rajendra P.,Helmke, Elisabeth,Fiebig, Heinz-Herbert,Laatsch, Hartmut
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p. 1031 - 1035
(2007/10/03)
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- New 1,4-anthracene-9,10-dione derivatives as potential anticancer agents
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The amino-substituted anthracene-9,10-dione (9,10-anthraquinone) derivatives represent one of the most important classes of potential anticancer agents. To better understand the basic rules governing DNA sequence specificity, we have recently synthesized a new class of d- and l- aminoacyl-anthraquinone derivatives. We have tested these new compounds as cytotoxic agents, and we have correlated their activity with the configuration of the chiral aminoacyl moiety. Molecular modeling studies have been performed to compare the test drugs in terms of steric overlapping. (C) 2000 Elsevier Science S.A.
- Zagotto,Supino,Favini,Moro,Palumbo
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- A Direct Route for the Regioselective Synthesis of Hydroxylated Aromatic Cycloalkanediones
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A "one-pot" regioselective synthesis of hydroxylated aromatic cycloalkanediones 1 from phenols or their methyl ethers and aliphatic dicarboxylic acid chlorides is reported.
- Sartori, Giovanni,Bigi, Franca,Goffredi, Gino,Maggi, Raimondo,Portioli, Roberto,Casnati, Giuseppe
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p. 2061 - 2079
(2007/10/02)
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- An EPR Study of a Model System for the Initial Oxygen Activation Process Caused by Adriamycin-Iron System
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1,4-Dihydroxyanthraquinone, a model compound for Adriamycin, is reduced by Fe2+-ADP complex to generate semiquinone, while by Fe2+-phosphate complex to hydroquinone.The difference is explained in terms of the higher redox potential of the latter reducing agent.Similar reduction reactions were observed in the case of the drug.
- Tachibana, Masahiko,Tero-Kubota, Shozo,Iwaizumi, Masamoto
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p. 933 - 936
(2007/10/02)
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- A NOVEL RING CLOSURE REACTION BETWEEN 1,4-DIHYDROXYANTHRAQUINONE AND ETHYLENEDIAMINE PROMOTED BY COPPER IONS
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The reaction of 1,4-dihydroxyanthraquinone with ethylenediamine in the presence of Cu(I)Cl or Cu(II)Cl2 gave 6-hydroxy-1,2,3,4-tetrahydronaphtho-(2,3-f)-quinoxaline-7,12-dione in quantitative yield at ambient temperature.The reaction was promoted greatly by copper ions.The possible mechanism and the role of copper ions were discussed.
- Matsuoka, Masaru,Makino, Yoshinobu,Takei, Toshio,Kitao, Teijiro
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p. 743 - 744
(2007/10/02)
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