84754-86-9

Basic information

• Product Name: Ai3-18244
• Synonyms: 1,2-Dihydroxyanthrachinon [czech];Ai3-18244
• CAS NO: 84754-86-9
• Molecular Formula: C14H8O4
• Molecular Weight: 240.21092
• Mol File: 84754-86-9.mol
• Article Data: 17

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Ai3-18244(CAS DataBase Reference)
• NIST Chemistry Reference: Ai3-18244(84754-86-9)
• EPA Substance Registry System: Ai3-18244(84754-86-9)

Safety Data

• Hazardous Substances Data: 84754-86-9(Hazardous Substances Data)

Upstream product

• 85-44-9 phthalic anhydride 
• 120-80-9 benzene-1,2-diol 
• 64-17-5 ethanol 
• 605-32-3 2-hydroxy-9,10-anthraquinone 
• 82-34-8 1-nitroanthraquinone 
• 129-43-1 1-hydroxyanthraquinone 
• 83-61-4 Alizarin S 
• 568-98-9 1-amino-2-hydroxy-9,10-anthracenedione 
• 6471-81-4 1-chloro-2-hydroxy-anthraquinone 
• 141-52-6 sodium ethanolate 
• 633-68-1 2,3-dibromo-9,10-anthraquinone 
• 108537-38-8 3,4-dihydroxy-9,10-dioxo-9,10-dihydro-anthracene-2-sulfonic acid ; diammonium salt 
• 108537-38-8 3,4-dihydroxy-9,10-dioxo-9,10-dihydro-anthracene-2-sulfonic acid ; triammonium compound 
• 86705-99-9 1,2,1',2'-tetrahydroxy-9H,9'H-[9,9']bianthryl-10,10'-dione 

Downstream Products

• 108-95-2 phenol 
• 83-61-4 Alizarin S 
• 96652-08-3 3,4-dihydroxy-9,10-dioxo-9,10-dihydro-anthracene-1-sulfonic acid 
• 22516-62-7 2-(benzyloxy)-1-hydroxyanthracene-9,10-dione 
• 75697-69-7 1-hydroxy-9,10-dioxo-9,10-dihydroanthracen-2-yl benzoate 
• 121151-69-7 triphenylgermyl 1,2-dihydroxy-9,10-anthraquinone adduct 

Relevant articles and documents

Evaluation of a series of 9,10-anthraquinones as antiplasmodial agents

Background: A phytochemical study on medicinal plants used for the treatment of fever and malaria in Africa yielded metabolites with potential antiplasmodial activity, many of which are Anthraquinones (AQ). AQs have similar sub-structure as naphthoquinones and xanthones, which were previously reported as novel antiplasmodial agents. Objective: The present study aimed to investigate the structural requirements of 9,10-anthraquinones with hydroxy, methoxy and methyl substituents to exert strong antiplasmodial activity and to investigate their possible mode of action. Methods: Thirty-one AQs were synthesized through Friedel-Crafts reaction and assayed for antiplasmodial activity in vitro against Plasmodium falciparum (3D7). The selected compounds were tested for toxicity and probed for their mode of action against β-hematin dimerization through HRP2 and lipid catalyses. The most active compounds were subjected to a docking study using AutoDock 4.2. Results: The active AQs have similar common structural characteristics. However, it is difficult to establish a structure-activity relationship as certain compounds are active despite the absence of the structural features exhibited by other active AQs. They have either ortho- or meta-arranged substituents and one free hydroxyl and/or carbonyl groups. When C-6 is substituted with a methyl group, the activity of AQs generally increased. 1,3-DihydroxyAQ (15) showed good antiplasmodial activity with an IC50 value of 1.08 μM, and when C-6 was substituted with a methyl group, 1,3-dihydroxy-6-methylAQ (24) showed stronger antiplasmodial activity with an IC50 value of 0.02μM, with better selectivity index. Compounds 15 and 24 showed strong HRP2 activity and mild toxicity against hepatocyte cells. Molecular docking studies showed that the hydroxyl groups at the ortho (23) and meta (24) positions are able to form hydrogen bonds with heme, of 3.49 A and 3.02 A, respectively. Conclusion: The activity of 1,3-dihydroxy-6-methylAQ (24) could be due to their inhibition against the free heme dimerization by inhibiting the HRP2 protein. It was further observed that the anthraquinone moiety of compound 24 bind in parallel to the heme ring through hydrophobic interactions, thus preventing crystallization of heme into hemozoin.

Synthesis and antitumor activities of novel α-aminophosphonate derivatives containing an alizarin moiety

A series of novel α-aminophosphonate derivatives containing an alizarin moiety (6-7) was designed and synthesized as antitumor agents. MTT (3-(4, 5-dimethylthiazol-2-yl)-2, 5-diphenyl tetrazolium bromide) assay results indicated that most compounds exhibited moderate to high inhibitory activity against KB, NCI-H460, HepG 2, A549, MGC-803, Hct-116, CNE and Hela tumor cell lines. The action mechanism of representative compounds 7h, 7j and 7n were investigated by fluorescence staining assays, flow cytometric analysis and real-time polymerase chain reaction (PCR) assays, which indicated that these compounds induced apoptosis and involved G1 phase arrest by increasing the production of intracellular Ca2+ and reactive oxygen species (ROS) and affecting associated enzymes and genes. The results demonstrated that these compounds may induce apoptosis through a mitochondrion-dependent pathway.

An anthraquinone scaffold for putative, two-face bim BH3 α-helix mimic

Bim BH3 peptide features an α-helix with hotspot residues on multiple faces. Compound 5 (6-bromo-2,3-dihydroxyanthracene-9,10-dione), which adopts a rigid-plan amphipathic conformation, was designed and evaluated as a scaffold to mimic two faces of Bim α-helix. It reproduced the functionalities of both D67 and I65 on two opposing helical sides. Moreover, it maintained the two-faced binding mode during further evolution. A putative BH3 α-helix mimic and nanomolar Bcl-2/Mcl-1 dual inhibitor, 6, was obtained based on the structure of 5.