反式-1,2-二羟基-1,2-二氢山油柑碱系列酯类的合成及其生物活性

Synthesis and biological activity of esters in the trans-1,2-dihydroxy-1,2-dihydroacronycine series.

作者信息

Magiatis P, Mitaku S, Skaltsounis A L, Tillequin F, Koch M, Pierré A, Atassi G

机构信息

Laboratory of Pharmacognosy, University of Athens, Greece.

出版信息

J Nat Prod. 1998 Feb;61(2):198-201. doi: 10.1021/np970427s.

DOI:10.1021/np970427s

Abstract

Permanganate oxidation of acronycine (1) led to keto alcohol 4 which could be reduced to trans-1,2-dihydroxy-1,2-dihydroacronycine (3) using NaBH4. Acylation of 3 afforded 12, 13, and 14. These esters (12, 13, and 14) were more potent than 1 when tested against L-1210 cells in vitro. Diacetate 12 was evaluated in vivo against murine P-388 leukemia and was markedly active at a dose 16-fold lower than acronycine itself. Comparison of these results with those recently obtained in the cis-1,2-dihydroxy-1,2-dihydroacronycine series is discussed.

摘要

巴枯宁（1）经高锰酸盐氧化生成酮醇4，使用硼氢化钠可将其还原为反式-1,2-二羟基-1,2-二氢巴枯宁（3）。3经酰化反应得到12、13和14。在体外对L-1210细胞进行测试时，这些酯（12、13和14）比1更具活性。双乙酸酯12在体内针对小鼠P-388白血病进行了评估，其活性剂量比巴枯宁本身低16倍。讨论了将这些结果与最近在顺式-1,2-二羟基-1,2-二氢巴枯宁系列中获得的结果进行比较的情况。

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