3963-78-8

Basic information

• Product Name: 3-amino-1,2-dihydroxyanthracene-9,10-dione
• Synonyms: 3-amino-1,2-dihydroxyanthracene-9,10-dione;3-Amino-1,2-dihydroxy-9,10-anthracenedione;3-Amino-1,2-dihydroxyanthraquinone;3-Aminoalizarin;Alizarin maroon;β-Aminoalizarin;3-amino-1,2-dihydroxy-9,10-anthraquinone;3-azanyl-1,2-dihydroxy-anthracene-9,10-dione
• CAS NO: 3963-78-8
• Molecular Formula: C₁₄H₉NO₄
• Molecular Weight: 255.22556
• Mol File: 3963-78-8.mol
• Article Data: 4

Chemical Properties

• Melting Point: >359.85°C
• Boiling Point: 398.45°C (rough estimate)
• Flash Point: 253.7°C
• Appearance: /
• Density: 1.2797 (rough estimate)
• Vapor Pressure: 1.86E-10mmHg at 25°C
• Refractive Index: 1.4700 (estimate)
• PKA: 6.97±0.20(Predicted)
• CAS DataBase Reference: 3-amino-1,2-dihydroxyanthracene-9,10-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 3-amino-1,2-dihydroxyanthracene-9,10-dione(3963-78-8)
• EPA Substance Registry System: 3-amino-1,2-dihydroxyanthracene-9,10-dione(3963-78-8)

Safety Data

• Hazardous Substances Data: 3963-78-8(Hazardous Substances Data)

Usage

InChI:InChI=1/C14H9NO4/c15-9-5-8-10(14(19)13(9)18)12(17)7-4-2-1-3-6(7)11(8)16/h1-5,18-19H,15H2

Upstream product

• 7647-01-0 hydrogenchloride 
• 859333-71-4 11-acetoxy-2-methyl-anthra[2,3-d]oxazole-5,10-dione 
• 568-93-4 3-nitroalizarin 
• 7664-93-9 sulfuric acid 
• 909878-64-4 meso-erythritol 
• 69-65-8 mannitol 
• 50-99-7 glucose 
• 57-50-1 Sucrose 
• 7783-06-4 hydrogen sulfide 
• 72-48-0 1,2-dihydroxy-9,10-anthracenedione 

Downstream Products

• 34649-71-3 11-hydroxy-2-phenyl-anthra[2,3-d]oxazole-5,10-dione 
• 568-02-5 alizarine Blue 

Relevant articles and documents

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.

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.