肉桂酸羽扇烷醇酯的合成及其抗癌活性
Synthesis of Lupanol Cinnamate and Its Anticancer Activities

作者: 李伟杰 :韩山师范学院化学与环境工程学院,广东 潮州;

关键词: 肉桂酸羽扇烷醇酯合成抗癌活性Lupanol Cinnamate Synthesis Anticancer Activity

摘要:
以N,N'-二环己基碳二亚胺(DCC)为缩合剂,4-二甲氨基吡啶(DMAP)为催化剂,羽扇烷醇和肉桂酸在二氯甲烷中室温反应24 h,合成了新化合物肉桂酸羽扇烷醇酯,产率为81.6%。研究了肉桂酸羽扇烷醇酯体外对食管鳞癌细胞Eca-109、TE-1和EC-9706增殖的抑制活性。结果表明肉桂酸羽扇烷醇酯对上述3株实验癌细胞的增殖均有良好的抑制活性,其抗癌活性与阿霉素相近。

Abstract: Lupanol was reacted with cinnamic acid for 24 h in dichloromethane at room temperature to give lupanol cinnamate at 81.6% yield in the presence of N,N'-dicyclohexylcarbodiimide (DDC) as dehydrating agent and 4-dimethylaminopyridine (DMAP) as catalyst. It was evaluated for in vitro antitumor activities against the human esophageal squamous cell carcinoma cell lines Eca- 109, TE-1 and EC-9706. The results showed that lupanol cinnamate had good inhibitory activities against the above three tested cancer cell lines and its anticancer activities were near to those of adriamycin.

文章引用: 李伟杰 (2016) 肉桂酸羽扇烷醇酯的合成及其抗癌活性。 有机化学研究, 4, 1-5. doi: 10.12677/JOCR.2016.41001

参考文献

[1] 庾石山. 三萜化学[M]. 北京: 化学工业出版社, 2008: 169-171.

[2] Tolstikova, T.G., Sorokina, I.V., Tolstikov, G.A., Tolstikov, A.G. and Flekhter, O.B. (2006) Biological Activity and Pharmacological Prospects of Lupane Terpe-noids: II. Semisynthetic Lupane Derivatives. Russian Journal of Bioorganic Chemistry, 32, 261-276.
http://dx.doi.org/10.1134/S1068162006030083

[3] Yu, D., Sakurai, Y., Chen, C.-H., Chang, F.-R., Huang, L., Kashiwada, Y. and Lee, K.-H. (2006) Anti-AIDS Agents 69. Moronic Acid and Other Triterpene Derivatives as Novel Potent Anti-HIV Agents. Journal of Medicinal Chemistry, 49, 5462-5469.
http://dx.doi.org/10.1021/jm0601912

[4] Li, W.-J., Hao, J. and and Xiao, Y.-Y. (2013) Synthesis and in Vitro Antitumor Activities of Lupeol Dicarboxylic Acid Monoester Derivatives. Archives of Pharmacal Research, 36, 1447-1453.
http://dx.doi.org/10.1007/s12272-013-0155-x

[5] 李伟杰. 羽扇烷醇的合成[J]. 科技创新导报, 2012, 219(3): 136, 138.

[6] 李伟杰. 生物活性天然产物羽扇豆醇肉桂酸酯的合成[J]. 广东化工, 2012, 226(2): 43.

[7] 薄采颖, 毕良武, 王玉民, 赵振东. DCC及其在有机合成中的应用[J]. 化工时报, 2007, 21(10): 4-6, 13.

[8] 宋秀美, 汪朝阳, 毛郑州, 罗玉芬, 赵海军. 胆甾醇酯的合成研究进展[J]. 2008, 33(1): 59-67.

[9] 孟丽丽, 匡永清, 肖义军, 宿亮, 向顺, 谢斌. 二十二碳六烯酸双氢青蒿素酯的合成及其抗肿瘤活性的初步研究[J]. 化学研究与应用, 2009, 21(1): 123-126.

[10] 周静, 王静, 孙宝国. 阿魏酸糖酯合成的研究进展[J]. 食品工业科技, 2012, 33(16): 392-395.

[11] 徐祥浩, 李和生, 葛燕燕, 刘漫, 张姝妹. DCC缩合酯化法制备壳聚糖山梨酸酯的工艺研究[J]. 中国食品学报, 2014, 14(4): 29-36.

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