- Synthesis of new cytotoxic aminoanthraquinone derivatives via nucleophilic substitution reactions
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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 BuNH2 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 (IC50 1.1-13.0 μg/mL).
- Nor, Siti Mariam Mohd,Sukari, Mohd Aspollah Hj Md,Azziz, Saripah Salbiah Syed Abdul,Fah, Wong Chee,Alimon, Hasimah,Juhan, Siti Fadilah
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p. 8046 - 8062
(2013/08/23)
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- Markers for petroleum, method of tagging, and method of detection
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Liquid petroleum products are tagged with a marker which is a compound or mixture of compounds having the formula: wherein R2 is C1-C6 alkyl, and R2 and R3 are nothing or -O-(C1-C3 alkyl). The marker or markers can be detected by extraction from the liquid petroleum product with a mixture of 20 to 100 vol.% of an aqueous solution of up to 10 wt.% NaOH or KOH and up to 80 vol.% of a water-soluble organic cosolvent.
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- The Direct Alkylamination of α-Substituted Antraquinones Promoted bu Metal Ions
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The reaction of 1-amino-4-acylaminoantraquinones with piperidine in the presence of CoCl2 and atmospheric oxygen gave the 2-aminated products in 75-80percent and similar reaction of 1-hydroxyantraquinone or 1-aminoantraquinone-2-sulfonic acid with butylamine gave the corresponding 4-aminated products, respectively.The effects of the α-substituents and the role of metal salts were discussed.
- Matsuoka, Masaru,Takei, Toshio,Nakamura, Isao
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p. 2225 - 2226
(2007/10/02)
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