82-24-6

Usage

Synthesis Reference(s)

Synthesis, p. 528, 1976 DOI: 10.1055/s-1976-24108

Purification Methods

It is used for the detection of Al, Mg Cd, Zn, Mn, Cu, Hg, Fe, Co, Ni and Pb. The methyl ester gives red needles from AcOH, m 228o. The ethyl ester, m 198o, crystallises also as red needles from AcOH. [Locher & Fietz Helv Chim Acta 10 667 1927, Beilstein 14 II 419, 14 III 168.]

InChI:InChI=1/C15H9NO4/c16-12-10(15(19)20)6-5-9-11(12)14(18)8-4-2-1-3-7(8)13(9)17/h1-6H,16H2,(H,19,20)/p-1

Upstream product

• 82-23-5 1-chloro-9,10-dioxo-9,10-dihydro-anthracene-2-carboxylic acid 
• 36764-97-3 1-amino-9,10-dioxo-9,10-dihydro-anthracene-2-carbonitrile 
• 128-67-6 1-nitroanthraquinone-2-carboxylic acid 
• 74214-86-1 2-bromomethyl-1-nitro-anthraquinone 
• 127-09-3 sodium acetate 
• 95-50-1 1,2-dichloro-benzene 
• 129-15-7 1-nitro-2-methylanthraquinone 
• 84-54-8 2-methylanthracene-9,10-dione 
• 92439-31-1 2-methylanthraquinone-1-sulfonic acid 
• 6338-00-7 1-chloro-2-dibromomethyl-anthraquinone 
• 82-45-1 1-amino-9,10-anthracenedione 
• 24094-44-8 1-amino-2-hydroxymethyl-9,10-dioxo-9,10-dihydroanthracene 
• 85-44-9 phthalic anhydride 
• 108-88-3 toluene 

Downstream Products

• 6470-88-8 1-amino-2-anthraquinonecarbonyl chloride 
• 6363-90-2 1-Amino-4-bromoanthraquinone-2-carboxylic acid 
• 2058-02-8 1-amino-4-nitroanthraquinone-2-carboxylic acid 
• 4182-49-4 1-amino-N-cyclohexyl-9,10-dioxo-9,10-dihydroanthracene-2-carboxamide 
• 75535-00-1 1-amino-N-(2-methoxyphenyl)-9,10-dioxo-9,10-dihydroanthracene-2-carboxamide 
• 82-45-1 1-amino-9,10-anthracenedione 

Relevant academic research and scientific papers

CHARACTERISTIC FEATURES OF THE REACTION OF 3(5)-AMINO-5(3)-METHYLPYRAZOLE WITH 1-NITROANTHRAQUINONE-2-CARBOXYLIC ACID

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.

Novel anthraquinone compounds inhibit colon cancer cell proliferation via the reactive oxygen species/JNK pathway

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.

Design, Synthesis, Molecular Docking, and Biological Evaluation of New Emodin Anthraquinone Derivatives as Potential Antitumor Substances

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.

Syntheses of 2-substituted 1-amino-4-bromoanthraquinones (bromaminic acid analogues) - Precursors for dyes and drugs

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.

TRANSFORMATIONS OF 1-AZIDO-2-ANTHRAQUINONECARBOXYLIC ACID AND ITS ESTERS

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.

Preparation and Evaluation of 2-Substituted Anthraquinones Based on the Anthracyclines

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.

Process for the preparation of 1-aminoanthraquinones

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.

Process for preparing aminoanthraquinones

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.

Process for the production of aminoanthraquinone compounds

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.