568-93-4

Usage

Uses

Used in Textile Industry:
Acid Mordant Orange 14 is used as a dye for coloring cloth that has been mordanted with aluminum, resulting in an orange color, and with iron, resulting in a red to violet color. It is chosen for its fastness properties, which ensure that the color remains vibrant and resistant to various conditions, such as ironing, light exposure, and washing.
Used as an Indicator:
Acid Mordant Orange 14 is also used as an indicator in a saturated alcohol solution. It exhibits a color change from golden orange to flat yellow in water at a pH range of 2.0-4.0, and from yellow to purplish red at a pH range of 5.0-6.5. This property makes it useful for monitoring changes in acidity or alkalinity in various applications.
Used in Pharmaceutical Research:
Although not explicitly mentioned in the provided materials, Acid Mordant Orange 14 may also have potential applications in the development of allosteric PGAM1 inhibitors, which are effective at suppressing the proliferation of pancreatic ductal adenocarcinoma cells. This is based on the mention of 1,2-Dihydroxy-3-nitroanthraquinone (CAS# 568-93-4) being useful for this purpose, and the structural similarity between the two compounds.

Preparation

(a) in the presence of boric acid 1,2-Dihydroxyanthracene-9,10-dione?in sulfuric acid in the nitration; (b) 1,2-Dihydroxyanthracene-9,10-dione?in glacial acetic acid, toluene, petroleum ether or the nitration of nitrobenzene.

Standard

Ironing Fastness

Alkali

Acid

ISO

3-4

Purification Methods

Crystallise the dye from AcOH (m 244-245o). It has max at 494nm (H2SO4) and forms Cu salts. [Beilstein 8 H 447, 8 II 491, 8 III 3774, 8 IV 2359.]

InChI:InChI=1/C14H7NO6/c16-11-6-3-1-2-4-7(6)12(17)10-8(11)5-9(15(20)21)13(18)14(10)19/h1-5,18-19H

Upstream product

• 72-48-0 1,2-dihydroxy-9,10-anthracenedione 
• 18084-26-9 3-Bromoalizarin 

Downstream Products

• 3963-78-8 3-amino-1,2-dihydroxyanthraquinone 

Relevant academic research and scientific papers

Development of anthraquinone analogues as phosphoglycerate mutase 1 inhibitors

Phosphoglycerate mutase 1 (PGAM1) coordinates glycolysis and biosynthesis to promote cancer cell proliferation, and is believed to be a promising target for cancer therapy. Herein, based on the anthraquinone scaffold, we synthesized 31 anthraquinone derivatives and investigated the structure?activity relationship (SAR). The 3-substitient of sulfonamide on the anthraquinone scaffold was essential for maintaining potency and the modifications of the hydroxyl of alizarin would cause a sharp decrease in potency. In the meantime, we determined the co-crystal structure of PGAM1 and one of the anthraquinone inhibitors 9i with IC50 value of 0.27 μM. The co-crystal structure revealed that F22, K100 and R116 of PGAM1 were critical residues for the binding of inhibitors which further validated the SAR. Consistent with the crystal structure, a competitive assay illustrated that compound 9i was a noncompetitive inhibitor. In addition, compound 9i effectively restrained different lung cancer cells proliferation in vitro. Taken together, this work provides reliable guide for future development of PGAM1 inhibitors and compound 9i may act as a new leading compound for further optimization.

Synthesis and biological evaluation of anthraquinone derivatives as allosteric phosphoglycerate mutase 1 inhibitors for cancer treatment

Phosphoglycerate mutase 1 (PGAM1) coordinates glycolysis, pentose phosphate pathway, and serine synthesis to promote tumor growth through the regulation of its substrate 3-phosphoglycerate (3 PG) and product 2-phosphoglycerate (2 PG). Herein, based on our previously reported PGAM1 inhibitor PGMI-004A, we have developed anthraquinone derivatives as novel allosteric PGAM1 inhibitors and the structure?activity relationship (SAR) was investigated. In addition, we determined the co-crystal structure of PGAM1 and the inhibitor 8g, demonstrating that the inhibitor was located at a novel allosteric site. Among the derivatives, compound 8t was selected for further study, with IC50 values of 0.25 and approximately 5 μM in enzymatic and cell-based assays, respectively. Mechanistically, compound 8t reduced the glycolysis and oxygen consumption rate in cancer cells, which led to decreased adenosine 5′-triphosphate (ATP) production and subsequent 5′ adenosine monophosphate-activated protein kinase (AMPK) activation. The inhibitor 8t also exhibited good efficacy in delaying tumor growth in H1299 xenograft model without obvious toxicity. Taken together, this proof-of-principle work further validates PGAM1 as a potential target for cancer therapy and provides useful information on anti-tumor drug discovery targeting PGAM1.

9,10-anthraquinone compound, pharmaceutically-acceptable salts and pharmaceutical application thereof

The invention belongs to the field of pharmaceutical chemistry and relates to a 9,10-anthraquinone compound and a pharmaceutical application thereof, in particular to the 9,10-anthraquinone compound and the application thereof in the preparation of a phosphoglycerate mutase inhibitor and in the preparation of drugs for treating cancer. In particular, the invention discloses the application of the9,10-anthraquinone compound shown in the structure of a formula I, pharmaceutically-acceptable salts thereof, or a pharmaceutical composition taking the 9,10-anthraquinone compound as an effective active ingredient in preparing drugs for preventing and treating tumors. The compound can inhibit phosphoglycerate mutase activity and reduce cell metabolism level, and can be used for treating diseasessuch as solid tumors and blood tumors, and the tumors involved are pancreatic cancer, lung cancer, liver cancer, gastric cancer, esophageal cancer, intestinal cancer, breast cancer, cervical cancer, leukemia and melanoma.

One pot synthesis of 3-nitro-1,2-dihydroxyanthraquinone and 1-hydroxy-9,10-dioxo-9,10-dihydroanthracen-2-yl benzoate using microwave irradiation

An efficient method for the one pot synthesis of 3-nitro-1,2- dihydroxyanthraquinone and 1-hydroxy-9,10-dioxo-9,10-dihydroanthracen-2-yl benzoate (an anthraquinone derivative) under microwave irradiation conditions. The structures of newly synthesized compounds have been established by analytical data that includes elemental analysis, mass spectra, IR spectra and melting point.