128-67-6

Basic information

• Product Name: kyselina1-nitroanthrachinon-2-karboxylova
• Synonyms: 1-nitro-10-anthraquinone-2-carboxylicacid;1-nitro-2-anthraquinonecarboxylicacid;1-nitro-2-carboxyanthraquinone;9,10-dihydro-1-nitro-9,10-dioxo-2-anthroicaci;9,10-dihydro-1-nitro-9,10-dioxo-2-anthroicacid;kyselina1-nitroanthrachinon-2-karboxylova;9,10-dihydro-1-nitro-9,10-dioxoanthracene-2-carboxylic acid;9,10-Dihydro-1-Nitro-9,10-Dioxoanthralene-2-Carboxylic Acid
• CAS NO: 128-67-6
• Molecular Formula: C₁₅H₇NO₆
• Molecular Weight: 297.21918
• EINECS: 204-904-8
• Product Categories: Intermediates of Dyes and Pigments
• Mol File: 128-67-6.mol

Chemical Properties

• Boiling Point: 438.74°C (rough estimate)
• Flash Point: 252.3°C
• Appearance: /
• Density: 1.3788 (rough estimate)
• Vapor Pressure: 5.22E-15mmHg at 25°C
• Refractive Index: 1.6231 (estimate)
• CAS DataBase Reference: kyselina1-nitroanthrachinon-2-karboxylova(CAS DataBase Reference)
• NIST Chemistry Reference: kyselina1-nitroanthrachinon-2-karboxylova(128-67-6)
• EPA Substance Registry System: kyselina1-nitroanthrachinon-2-karboxylova(128-67-6)

Safety Data

• Hazardous Substances Data: 128-67-6(Hazardous Substances Data)

Usage

Uses

Used in Textile Industry:
Kyselina 1-nitroanthrachinon-2-karboxylova is used as a dye intermediate for the production of colored pigments in the textile industry. Its vibrant color properties make it suitable for dyeing and printing processes, enhancing the visual appeal and variety of textile products.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, kyselina 1-nitroanthrachinon-2-karboxylova serves as a precursor in the synthesis of various organic compounds. Its chemical structure allows for the development of new pharmaceutical agents, potentially contributing to the advancement of medicinal chemistry.
Used in Chemical Industry:
Similarly, in the chemical industry, this compound is utilized as a precursor for the synthesis of a range of organic compounds. Its versatility in chemical reactions makes it a valuable component in the creation of diverse chemical products, expanding the scope of chemical applications.

InChI:InChI=1/C15H7NO6/c17-13-7-3-1-2-4-8(7)14(18)11-9(13)5-6-10(15(19)20)12(11)16(21)22/h1-6H,(H,19,20)/p-1

Upstream product

• 129-15-7 1-nitro-2-methylanthraquinone 
• 80685-73-0 ethyl 1-nitroanthraquinone-2-carboxylate 
• 105-56-6 ethyl 2-cyanoacetate 
• 7664-93-9 sulfuric acid 
• 74214-86-1 2-bromomethyl-1-nitro-anthraquinone 
• 7697-37-2 nitric acid 
• 84-54-8 2-methylanthracene-9,10-dione 
• 85-44-9 phthalic anhydride 
• 108-88-3 toluene 

Downstream Products

• 82-24-6 1-aminoanthraquinone-2-carboxylic acid 
• 82-23-5 1-chloro-9,10-dioxo-9,10-dihydro-anthracene-2-carboxylic acid 
• 602-10-8 1-nitro-9,10-dioxo-9,10-dihydroanthracene-2-carbonyl chloride 
• 82-45-1 1-amino-9,10-anthracenedione 
• 3737-76-6 Vat Red KKh 
• 95310-34-2 3-methoxycarbonylanthra<1,9-cd>-6-isoxazolone 
• 80685-64-9 1-nitro-9,10-dioxo-9,10-dihydroanthracene-2-carboxanilide 
• 100440-89-9 N-benzyl-1-nitro-9,10-dioxo-9,10-dihydroanthracene-2-carboxamide 
• 442631-97-2 2-phenyl-2,3,6,11-tetrahydroanthra[2,1-d]isothiazole-3,6,11-trione 
• 430433-65-1 1-methylthio-9,10-dioxo-9,10-dihydroanthracene-2-carboxanilide 
• 430433-68-4 1-ethylthio-9,10-dioxo-9,10-dihydroanthracene-2-carboxanilide 
• 430433-66-2 N-benzyl-1-methylthio-9,10-dioxo-9,10-dihydroanthracene-2-carboxamide 
• 610788-23-3 2-benzyl-2,3,6,11-tetrahydroanthra[2,1-d]isothiazole-3,6,11-trione 
• 430433-69-5 N-benzyl-1-ethylthio-9,10-dioxo-9,10-dihydroanthracene-2-carboxamide 

Relevant articles and documents

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.

Preparation of 1-nitroanthraquinone-2-carboxylic acids

1-Nitroanthraquinone-2-carboxylic acids of the general formula I STR1 where X is hydrogen, chlorine or bromine, are prepared by oxidizing a 1-nitro-2-methylanthraquinone of the general formula II STR2 with nitric acid in an organic reaction medium.

REACTION OF α-HALOGENO- AND α-NITROANTHRAQUINONES WITH THE ANIONS OF CH ACIDS IV. REACTION OF 1-NITROANTHRAQUINONE-2-CARBOXYLIC ACID WITH CYANOACETIC ESTER AND MALONONITRILE

The reaction of 1-nitroanthraquinone-2-carboxylic acid with cyanoacetic ester and malononitrile in the presence of a base leads to nucleophilic substitution of the nitro group and acylation of the CH acid molecule by the carboxyl group to the corresponding 1-alkyl-2-acylanthraquinones.Subsequent treatment of the latter with sulfuric acid leads to 2-hydroxy-7H-dibenzoquinoline-3,4-dicarboxylic acid.The N-phenylamide of the latter is produced by the reaction of 1-nitroanthraquinone-2-carbanilide with cyanoacetic ester.

Preparation of 1-nitroanthraquinone-2-carboxylic acid

1-Nitroanthraquinone-2-carboxylic acid of the formula I STR1 is prepared by treating novel 2-substituted 1-nitroanthraquinones of the general formula II STR2 where R is --CH=CH--R1 or --CH2 --CHO, where R1 is C1 -C5 -dialkylamino or a cyclic 5- or 6-membered amine which may contain further hetero atoms, with oxidizing agents free of heavy metal.

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.