| 姚连琦,秦立玙,李 雯,刘德龙.丹参酮IIA衍生物的合成[J].,2018,(2):205-209 |
| 丹参酮IIA衍生物的合成 |
| Synthesis of Tanshinone IIA Derivatives |
| 投稿时间：2017-05-28 修订日期：2017-06-23 |
| DOI：10.13241/j.cnki.pmb.2018.02.002 |
| 中文关键词: 丹参酮IIA 衍生物 还原胺化 胺甲基 合成 |
| 英文关键词: Tanshinone IIA Derivative Reductive amination Aminomethyl group Synthesis |
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| 中文摘要: |
| 摘要 目的：丹参酮IIA是中药丹参的脂溶性成分，具有抗肿瘤、抗氧化、抗心脑血管疾病等多种生理活性。本文拟对其进行结构改造以获得活性更好的丹参酮IIA衍生物。方法：首先，以丹参酮IIA为原料，通过Vilsmeier反应在其16-位引入醛基，再与醋酸胺进行还原胺化反应，以较高收率得到16-位胺甲基取代的丹参酮IIA衍生物。接着，对其氨基进行修饰，得到10个不同N-取代的丹参酮IIA衍生物。同时考察反应温度、反应溶剂和反应时间等条件对还原胺化反应的影响，确定最佳反应条件。结果：通过1H-NMR、13C-NMR以及LC-MS对所有产物结构进行了确认。还原胺化反应的最佳反应条件为：以1,2-二氯乙烷为溶剂，温度保持40 ℃，反应时间为2 h。结论：反应步骤简单、条件温和、产率较高，是合成16-位取代的丹参酮IIA衍生物的理想方法。 |
| 英文摘要: |
| ABSTRACT Objective: Tanshinone IIA is a lipophilic component of traditional Chinese medicine Salvia miltiorrhiza. It has various physiological activities such as anti-tumor, anti-oxidation, anti-cardiovascular and cerebrovascular diseases. Herein, we report the structure modification of Tanshinone IIA to obtain its derivatives with better activity. Structural modification is necessary due to its low activity. Methods: A Vilsmeier reaction of Tanshinone IIA was developed to provide an intermediate with an aldehyde substituent at its 16-position. A 16-aminomethyl substituted Tanshinone IIA derivative was then obtained in high yield via a reductive amination reaction of the above mentioned intermediate with ammonium acetate. After modification of the amino group, 10 Tanshinone IIA derivatives bearing different N-substituents were obtained. The effect of reaction temperature, solvent, time on the reductive amination reaction was investigated. Results: Structures of all the desired products were confirmed by 1H-NMR, 13C-NMR and LC-MS analysis. The optimal reaction conditions were determined as follows: in 1,2-dichloroethane under 40 ℃ for 2 hours. Conclusion: The method provides a simple, mild and efficient synthesis of Tanshinone IIA derivatives. |
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