39008-90-7

Basic information

• Product Name: 9,10-Anthracenedione, 1-hydroxy-4-methyl-
• CAS NO: 39008-90-7
• Molecular Formula: C15H10O3
• Molecular Weight: 238.243
• Mol File: 39008-90-7.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 9,10-Anthracenedione, 1-hydroxy-4-methyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 9,10-Anthracenedione, 1-hydroxy-4-methyl-(39008-90-7)
• EPA Substance Registry System: 9,10-Anthracenedione, 1-hydroxy-4-methyl-(39008-90-7)

Safety Data

• Hazardous Substances Data: 39008-90-7(Hazardous Substances Data)

Upstream product

• 85-44-9 phthalic anhydride 
• 106-44-5 p-cresol 
• 7446-70-0 aluminium trichloride 
• 79-34-5 1,1,2,2-tetrachloroethane 

Downstream Products

• 96179-17-8 4,9,10-Trihydroxy-1-methyl-9,10-diphenyl-9,10-dihydro-anthracen 
• 107664-52-8 4.4'-Dimethyl-9.10.9'.10'-tetraphenyl-dianthryl-(2.2')-chinon-(1.1') 
• 96069-25-9 4-Hydroxy-1-methyl-9.10-diphenyl-anthracen 
• 610-48-0 1-methylanthracene 

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.