- CHARACTERISTIC FEATURES OF THE REACTION OF 3(5)-AMINO-5(3)-METHYLPYRAZOLE WITH 1-NITROANTHRAQUINONE-2-CARBOXYLIC ACID
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In the reaction of 3(5)-amino-5(3)-methylpyrazole with 1-nitroanthraquinone-2-carboxylic acid in sulfolane at 150 deg C, 2-methylpyrazolonaphthoquinazoline-5,10.13-trione is formed with an admixture of 1-aminoanthraquinone-2-carboxylic acid and 1-aminoanthraquinone.Under similar conditions, from 4-amino-1,5-dimethylpyrazole, only 1-(1,5-dimethyl-4-pyrazolylamino)anthraquinone-2-carboxylic acid is formed.
- Perevalov, V. P.,Baryshnenkova, L. I.,Tsoi, K. S.
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- Novel anthraquinone compounds inhibit colon cancer cell proliferation via the reactive oxygen species/JNK pathway
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A series of amide anthraquinone derivatives, an important component of some traditional Chinese medicines, were structurally modified and the resulting antitumor activities were evaluated. The compounds showed potent anti-proliferative activities against eight human cancer cell lines, with no noticeable cytotoxicity towards normal cells. Among the candidate compounds, 1-nitro-2-acyl anthraquinone-leucine (8a) showed the greatest inhibition of HCT116 cell activity with an IC50 of 17.80 μg/mL. In addition, a correlation model was established in a three-dimensional quantitative structure-activity relationship (3D-QSAR) study using Comparative Molecular Field Analysis (CoMFA) and comparative molecular similarity index analysis (CoMSIA). Moreover, compound 8a effectively killed tumor cells by reactive oxygen species (ROS)-JNK activation, causing an increase in ROS levels, JNK phosphorylation, and mitochondrial stress. Cytochrome c was then released into cytoplasm, which, in turn activated the cysteine protease pathway and ultimately induced tumor cell apoptosis, suggesting a potential use of this compound for colon cancer treatment.
- Chen, Tinggui,Feng, Liheng,Guan, Yingying,Guo, Fang,Li, Yuying,Liu, Yaoming,Ma, Kaiqing,Su, Qiang,Wang, Zhuanhua,Zhang, Liwei,Zhou, Yuzhi
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- Design, Synthesis, Molecular Docking, and Biological Evaluation of New Emodin Anthraquinone Derivatives as Potential Antitumor Substances
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The emodin anthraquinone derivatives are generally used in traditional Chinese medicine due to their various pharmacological activities. In the present study, a series of emodin anthraquinone derivatives have been designed and synthesized, among which 1,3-dihydroxy-6,8-dimethoxyanthracene-9,10-dione is a natural compound that has been synthesized for the very first time, and 1,3-dimethoxy-5,8-dimethylanthracene-9,10-dione is a compound that has never been reported earlier. Interestingly, while total seven of these compounds showed neuraminidase inhibitory activity in influenza virus with inhibition rate more than 50 %, specific four compounds exhibited significant inhibition of tumor cell proliferation. The further results demonstrate that 1,3-dimethoxy-5,8-dimethylanthracene-9,10-dione showed the best anticancer activity among all the synthesized compounds by inducing highest apoptosis rate to HCT116 cancer cells and arresting their G0/G1 cell cycle phase, through elevation of intracellular level of reactive oxygen species (ROS). Moreover, the binding of 1,3-dimethoxy-5,8-dimethylanthracene-9,10-dione with BSA protein has thoroughly been investigated. Altogether, this study suggests the neuraminidase inhibitory activity and antitumor potential of the new emodin anthraquinone derivatives.
- Li, Yuying,Guo, Fang,Chen, Tinggui,Zhang, Liwei,Wang, Zhuanhua,Su, Qiang,Feng, Liheng
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- Syntheses of 2-substituted 1-amino-4-bromoanthraquinones (bromaminic acid analogues) - Precursors for dyes and drugs
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Anthraquinone (AQ) derivatives play a prominent role in medicine and also in textile industry. Bromaminic acid (1-amino-4-bromoanthraquinone-2-sulfonic acid) is an important precursor for obtaining dyes as well as biologically active compounds through the replacement of the C4-bromo substituent with different (ar)alkylamino residues. Here we report methods for the synthesis of bromaminic acid analogues bearing different substituents at the 2-position of the anthraquinone core. 1-Aminoanthraquinone was converted to its 2-hydroxymethyl-substituted derivative which, under different reaction conditions, yielded the corresponding carbaldehyde, carboxylic acid, and nitrile derivatives. The latter was further reacted to obtain 1-amino-2-tetrazolylanthraquinone. Subsequent bromination using bromine in DMF led to the corresponding bromaminic acid derivatives in excellent isolated yields (>90%) and high purities. Alternatively, 1-amino-4-bromo-2-hydroxymethylanthraquinone could be directly converted to the desired 2-substituted bromaminic acid analogues in high yields (85-100%). We additionally report the preparation of bromaminic acid sodium salt and 1-amino-2,4-dibromoanthraquinone directly from 1-aminoanthraquinone in excellent yields (94-100%) and high purities. The synthesized brominated AQs are valuable precursors for the preparation of AQ drugs and dyes.
- Malik, Enas M.,Baqi, Younis,Müller, Christa E.
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supporting information
p. 2326 - 2333
(2016/02/12)
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- TRANSFORMATIONS OF 1-AZIDO-2-ANTHRAQUINONECARBOXYLIC ACID AND ITS ESTERS
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When heated in nonpolar solvents, 1-azido-2-alkoxycarbonylanthraquinones are converted into 3-alkoxycarbonylanthra-6-isoxazolones.The product from the thermolysis of 1-azido-2-anthraquinonecarboxylic acid is 1,3-dihydroanthraisoxazole-3,6,11-trione.
- Gornostaev, L. M.,Lavrikova, T. I.
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p. 2012 - 2015
(2007/10/02)
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- Preparation and Evaluation of 2-Substituted Anthraquinones Based on the Anthracyclines
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Anthraquinones substituted at the 2 position with a basic side chain were prepared, and their binding to DNA was evaluated.All compounds showed an intercalative mode of binding to DNA; 1,4-dihydroxy derivatives bound more strongly than 1-hydroxy or nonhydroxylated compounds.Greatest DNA-binding activity was found where there were five atoms between the anthraquinone ring and the basic nitrogen.
- Bennett, Stephen,Sharples, Derek,Brown, Jeffrey R.
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p. 369 - 373
(2007/10/02)
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- Process for the preparation of 1-aminoanthraquinones
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A selective process for the preparation of 1-aminoanthraquinones by decarboxylation of the corresponding 1-aminoanthraquinone-2-carboxylic acid in an alkaline solution with an alkali metal hydrosulfite.
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- Process for preparing aminoanthraquinones
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A process for preparing aminoanthraquinones of high purity, which comprises catalytically hydrogenating nitroanthraquinones in the suspended state in an aqueous medium in the presence of a hydrogenating catalyst. In a preferred embodiment, the catalytic hydrogenation may be carried out in the presence of an organic or inorganic base, followed, if desired, by oxidizing the hydrogenation product.
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- Process for the production of aminoanthraquinone compounds
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The present invention concerns a novel process for the reduction of a nitro-anthraquinone compound of formula I: STR1 wherein M IS AN INTEGER 1, 2 OR 3, AND n is an integer 1, 2 or 3, The sum of m + n being 3, 4 or 5, and the rings A and B are either further substituted or unsubstituted, To the corresponding amino-anthraquinone compound which comprises reacting the compound of formula I with hydrazine in aqueous medium. The resulting amino-anthraquinone compounds are in general known and are useful intermediates in the production of anthraquinone dyestuffs.
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