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2,2-二甲基-2H-吡喃衍生生物碱I. 山油柑碱和苯并[b]山油柑碱的实用合成及其生物学性质

2,2-dimethyl-2H-pyran-derived alkaloids I. Practical synthesis of acronycine and benzo[b]acronycine and their biological properties.

作者信息

Motiur Rahman A F M, Liang Jing Lu, Lee Seung Ho, Son Jong Keun, Jung Mi-Ja, Kwon Youngjoo, Jahng Yurngdong

机构信息

College of Pharmacy, Yeungnam University, Gyeongsan, 712-749, Korea.

出版信息

Arch Pharm Res. 2008 Sep;31(9):1087-93. doi: 10.1007/s12272-001-1273-7. Epub 2008 Sep 20.

DOI:10.1007/s12272-001-1273-7
PMID:18806949
Abstract

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 microM level.

摘要

以邻氨基苯甲酸和间苯三酚为原料，通过三步反应制备了2,2 - 二甲基 - 2H - 吡喃衍生的生物碱吖啶酮及其去甲基类似物。1,3 - 二羟基吖啶酮与3 - 甲基 - 2 - 丁烯醛的苯基硼酸介导的分子间环化反应作为关键步骤，该步骤也应用于相关细胞毒性苯并[b]吖啶酮的合成。评估了所制备化合物对拓扑异构酶I和II的抑制活性及其细胞毒性。化合物2的细胞毒性与在20微摩尔水平对拓扑异构酶II的强抑制活性密切相关。

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