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KMID : 0043320080310091087
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Archives of Pharmacal Research
2008 Volume.31 No. 9 p.1087 ~ p.1093
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2,2-Dimethyl-2H-pyran-Derived Alkaloids I. Practical Synthesis of Acronycine and Benzo[b]acronycine and Their Biological Properties
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Rahman A.F.M.Motiur
Lee Seung-Ho
Kwon Young-Joo
Chung Mi-Ja
Jing Lu-Liang
Jahng Yurng-Dong
Son Jong-Keun
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Abstract
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The 2,2-dimethyl-2H-pyran-derived alkaloids acronycine and its demethylated congeners were prepared in three steps from anthranilic acid and phloroglucinol. The phenylboronic acid-mediated interamolecular cyclization reaction of 1,3-dihydroxyacridone and 3-methylbut-2-enal was employed as a key step, which was also applied to the synthesis of related cytotoxic benzo[b]acronycine. Inhibitory activities of the compounds prepared on topoisomerase I and II as well as their cytotoxicities were evaluated. Cytotoxicity of 2 is closely related to the strong inhibitory activity against topo II at 20 μM level.
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KEYWORD
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2,2-Dimethyl-2H-pyran-derived alkaloid, Acronycine, Phenylboronic acid, Benzo[b]acronycine, Topoisomerase inhibitor, Cytotoxicity
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