Synthesis And Antibacterial Activity Of Anthraquinone Derivatives

Anthraquinones are kinds of organic compounds widely exist in nature, especiallyin many plants and chinese herbal medicine, like chinese rhubarb have emodin andmadder have alizarin. These molecules contain unsaturated cyclohexyl-diketonestructure, that’s why they have prone to oxidation reduction properties, and they play animportant part of electron transportion in biological metabolic process, so they havevarieties of biological activity, such as antitumor, resistance mutation, anti-inflammatory,antiviral, antifungal, insecticidal antioxidant and so on. In this paper we selected1,2-dihydroxy anthraquinone and2-methyl anthraquinone who has no hydroxyl wereselected as the study objects.Firstly, the relatively cheap compounds of phthalic anhydride and catechol wereused as the initial raw materials to synthesis1,2-dihydroxy anthraquinone and2-methylanthraquinone and the physicochemical properties and spectral data were studied todetermine the structure of molecule.1,2-dihydroxy anthraquinone had extensiveapplication in developing of drug intermediate, because they were very importantorganic chemical intermediates. In this paper the methods of synthesis of1,2-dihydroxyanthraquinone were also studied. Furthermore, we studied the majorization reactionprocess to produce1,2-dihydroxy anthraquinone. We choosed concentrated sulfuric acidas solvent, and the raw material mole ratio phthalic anhydride: catechol: anhydrousaluminium trichloride was1.2:1:1.6, the temperature was120℃, the reaction time was4h, the yields can reach to55.2%ultimately. The yield was higher than reported ofothers (36%).Secondly, the1,2-dihydroxy anthraquinone derivative was studied. The study tookthe1,2-dihydroxy anthraquinone as the material, after two steps of williamson reactionand nuclear substitution reaction, to synthesis1-hydroxy-2-(2’-dimethyl-l-ethoxy)anthraquinone. The synthesis and separation conditions were studied, for laying thefoundation for this kind of compounds. We also studied the spectral data.Thirdly, the2-methylanthraquinone derivative was studied. The study took the2-methylanthraquinone as the material, after three steps of bromine atoms substitution, azide substitution and click cyclization, to synthesis2-(1-methyl chloride-1,2,3-triazole)anthraquinone. The synthesis and separation conditions were studied, for laying thefoundation for this kind of compounds. We also studied the spectral data.Finally, the compounds who were1,2-dihydroxy anthraquinone,1-hydroxy-2-(2’-dimethyl-ethoxy) anthraquinone,2-methylanthraquinone, and2-(1-methylchloride-1,2,3-three azole) anthraquinone were tested their antibacterial activity. Thecylinder plate method was adopted to study antibacterial activity. The test strains arestaphylococcus aureus and bacillus subtilis. The results shown that2-methylanthraquinone, and2-(1-methylchloride-1,2,3-triazole)anthraquinone had littleantibacterial activity on staphylococcus aureus and bacillus subtilis, but1,2-dihydroxyanthraquinone and1-hydroxy-2-(2’-dimethyl-ethoxy) anthraquinone had certainantibacterial activity on staphylococcus aureus and bacillus subtilis.