Acid-Catalyzed Dimerization of α-Asarone and Anticancer Evaluation of the Dimers

doi:10.6023/cjoc201303030

Chin. J. Org. Chem. ›› 2013, Vol. 33 ›› Issue (9): 1982-1987.DOI: 10.6023/cjoc201303030 Previous Articles Next Articles

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酸催化α-细辛脑二聚反应及其产物抗癌活性研究

徐盈盈^a, 梁志武^a, 刘开建^a, 陈辉^b, 向建南^a

a 湖南大学化学化工学院长沙 410082;
b 湖南大学生物学院长沙 410082

收稿日期:2013-03-19 修回日期:2013-05-23 发布日期:2013-05-31
通讯作者: 向建南 E-mail:jnxiang@hnu.cn
基金资助:
国家自然科学基金(No. 21276068);湖南省自然科学基金(No. 11JJ5008);湖南省科技厅重点(No. 2010SK2001)资助项目

Acid-Catalyzed Dimerization of α-Asarone and Anticancer Evaluation of the Dimers

Xu Yingying^a, Liang Zhiwu^a, Liu Kaijian^a, Chen Hui^b, Xiang Jiannan^a

a College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082;
b School of Biology, Hunan University, Changsha 410082

Received:2013-03-19 Revised:2013-05-23 Published:2013-05-31
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21276068), the Natural Science Foundation of Hunan Province (No. 11JJ5008), the Department of Science and Technology Foundation of Hunan Province (No. 2010SK2001)

The decarbonization of lignan a and dihydroindene b were synthesized through α-asarone by acid-catalyzed. Compounds a/b were identified by ¹H NMR, ¹³C NMR, MS and elemental analysis. The effects of catalysts, solvents and temperature on yields of a/b have been evaluated. The total yield of a/b reached 98% (a: 41%, b: 57%) with HCl as catalyst and ethanol as solvent at 45 ℃. The yield of compound a was up to 75% with AlCl₃ as catalyst and ethanol as solvent at 30 ℃, b was not formed in this condition, and the selectivity of a was 100%. When using BF₃·Et₂O as catalyst and methylene chloride as solvent at 45 ℃, the yield of compound a was 20% and b was formed in yield of 60%. The cytotoxic activities of two compounds against MCF-7, Bel-7402, A549 and Hela were evaluated in vitro by the MTT assay. The results indicated that compounds a/b exhibited better cytotoxic activities against four cancer cells than 5-Fu. Especially, the IC₅₀ values of a to MCF-7 and Hela reached 120.2 and 117.3 μmol·L^-1 as well as the IC₅₀ of b to MCF-7 and A549 reached 66.1 and 72.4 μmol·L^-1, respectively. At the same time, the concentration of a/b and time of operation to influence inhibitory activity were explored.

Key words: dihydroindene, decarbonization of lignan, selectivity, anticaner activity

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Xu Yingying, Liang Zhiwu, Liu Kaijian, Chen Hui, Xiang Jiannan. Acid-Catalyzed Dimerization of α-Asarone and Anticancer Evaluation of the Dimers[J]. Chin. J. Org. Chem., 2013, 33(9): 1982-1987.

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酸催化α-细辛脑二聚反应及其产物抗癌活性研究

Acid-Catalyzed Dimerization of α-Asarone and Anticancer Evaluation of the Dimers

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