81-64-1Relevant articles and documents
Clean process for synthesizing 1, 4-dihydroxy anthraquinone
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Paragraph 0020-0023, (2021/07/08)
The invention relates to the technical field of dye intermediates, and especially relates to a clean process for synthesizing 1, 4-dihydroxy anthraquinone. The process comprises the following steps: sequentially adding 98% sulfuric acid, boric anhydride, phthalic anhydride and hydroquinone into a dry reaction container according to a stoichiometric ratio, uniformly stirring, heating to 100-180 DEG C, and carrying out heat preservation reaction for 2-24 hours; after the heat preservation reaction is finished, cooling the materials, and transferring the materials into another reaction container for hydrolysis; and after hydrolysis is completed, cooling, filtering and washing to obtain the 1, 4-dihydroxy anthraquinone. According to the clean process for synthesizing the 1, 4-dihydroxy anthraquinone, provided by the invention, the dosage of the raw material phthalic anhydride can be reduced, the wastewater treatment difficulty is greatly reduced, and the production cost is also reduced; and meanwhile, the yield of the 1, 4-dihydroxy anthraquinone is also improved to a certain extent.
Evaluation of a series of 9,10-anthraquinones as antiplasmodial agents
Osman, Che Puteh,Ismail, Nor Hadiani,Widyawaruyanti, Aty,Imran, Syahrul,Tumewu, Lidya,Choo, Chee Yan,Ideris, Sharinah
, p. 353 - 363 (2019/06/20)
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 method of anthraquinone derivatives and tetracenedione derivatives through benzannulation reaction
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Paragraph 0029-0030; 0045, (2017/08/09)
The present invention relates to a method for synthesizing anthraquinone derivatives and tetracene dione derivatives through a benzannulation reaction, which presents a novel synthesis method, capable of processing synthesis easily, conveniently, and efficiently under mild conditions by an organic catalyst. The synthesis method uses an L-proline catalyst which is nontoxic, economical and easily available, compared to conventional production methods, thereby providing the anthraquinone derivatives and the tetracene dione derivatives through the one-pot benzannulation reaction of an α, β-unsaturated aldehyde compound, various 1,4-naphthoquinone compounds or 1,4-anthracenedione compounds. Various forms of anthraquinone derivatives or tetracene dione derivatives prepared by the synthesis method can be widely used for synthesis of natural products, dyes, and pharmaceutical products.COPYRIGHT KIPO 2017