Aminoanthraquinones were successfully synthesized via two reaction steps. 1,4-Dihydroxyanthraquinone (1) was first subjected to methylation, reduction and acylation to give an excellent yield of anthracene-1,4-dione (3), 1,4-dimethoxyanthracene-9,10-dione (5) and 9,10-dioxo-9,10-dihydroanthracene-1,4-diyl diacetate (7). Treatment of 1, 3, 5 and 7 with BuNH 2 in the presence of PhI(OAc) 2 as catalyst produced seven aminoanthraquinone derivatives 1a, b, 3a, and 5a-d. Amination of 3 and 5 afforded three new aminoanthraquinones, namely 2-(butylamino)anthracene-1,4-dione (3a), 2-(butylamino)anthracene-9,10-dione (5a) and 2,3-(dibutylamino)anthracene-9,10-dione (5b). All newly synthesised aminoanthraquinones were examined for their cytotoxic activity against MCF-7 (estrogen receptor positive human breast) and Hep-G2 (human hepatocellular liver carcinoma) cancer cells using MTT assay. Aminoanthraquinones 3a, 5a and 5b exhibited strong cytotoxicity towards both cancer cell lines (IC 50 1.1-13.0 µg/mL).
A new series of aminoanthraquinone were successfully synthesized via two step of reaction. Firstly 1,4-(dihyroxy)anthracene-9,10-dione was treated with butylamine in the presence of iodobenzene-diacetate to gives 2-(butylamino)-1,4-dihydroxyanthraquinone (1) (90%). In the second step 1 was subjected to reduction, methylation and acylation. Reduction using NaBH 4 result 2-(butyamino)anthracene-1,4-dione (2) where as methylation give a mixture of 2-(butyamino)-1-hydroxy-4-methoxyanthracene-9,10-dione (3a) and 2-(butyamino)-1,4-dimethoxyanthracene-9,10-dione (3b) in 2%, 32% and 25% respectively. The acylation produced 2-(butylamino)-9,10-dioxo-9,10-dihydroanthracene-1,4-diyl diacetate (4) in excellent yield. Characterizations of the products were obtained from the analysis by digital melting point equipment, Fourier Transform Infrared Spectroscopy (FT-IR), Direct Injection Mass Spectrometry (DI-MS), Gas Chromatography Mass Spectrometry (GC-MS) and also Nuclear Magnetic Resonance (NMR). Compound 4 shows good antimicrobial activities toward methicillinresistant Staphylococcus aureus (MRSA), Pseudomonas aeruginosa, Candida albicans and Escherichia coli with MIC value of 0.1, 0.1, 0.1 and 0.5 mg/mL respectively.
Five compounds comprising 8-O-4’-neolignan (7), two arylnaphthalene lignans (5, 8), aryldihydrobenzofuran neolignan (4), and lignan (6) were synthesised by enzymatic coupling reaction using horseradish peroxidase (HRP) between vanillin (1) with methyl ferulate (2) or methyl sinapate (3). All of these compounds, as well as previously synthesised palladium-catalysed coupling products of neolignan (9), 8-O-4'-neolignan (10), arylcoumarin (11), and lignan (12), were examined for larvicidal activity against Crocidolomia binotalis 2nd instar larvae. It revealed that seven out of nine synthesised compounds had a mortality rate of more than 90% after 24 hours of exposure. Neolignan (10) and lignan (6) demonstrated the strongest larvicidal activity with LD50 = 2.218 mg/L and LD50 = 1.678 mg/L, respectively compared to the standard azadirachtin (LD50 =2.818 mg/L). The results showed that the synthesised compounds have a high potential for use in the control of C. binotalis larvae and could be used in the development of new and more effective compounds as larvicides.
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