酸催化α-细辛脑二聚反应及其产物抗癌活性研究

doi:10.6023/cjoc201303030

有机化学 ›› 2013, Vol. 33 ›› Issue (9): 1982-1987.DOI: 10.6023/cjoc201303030 上一篇下一篇

研究简报

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)

文章分享

摘要/Abstract

以E-1-(2,4,5-三甲氧基苯基)-2-丙烯(α-细辛脑)为原料, 酸催化选择性合成脱碳木脂素类化合物a及二氢化茚类化合物b, 其结构经核磁﹑质谱和元素分析表征确认. 研究了催化剂种类、反应溶剂和温度等条件对两种化合物产率比的影响, 45 ℃时, HCl为催化剂, 乙醇为溶剂, 化合物a/b的总收率为98% (a: 41%, b: 57%); 30 ℃时, AlCl₃为催化剂, 乙醇为溶剂, 化合物a的产率可达75%, 没有b生成, 对a的选择性为100%; 45 ℃时, 以BF₃·Et₂O溶液为催化剂, CH₂Cl₂为溶剂, 化合物a的产率为20%, 化合物b的产率可达60%. 采用MTT法, 分别评价了化合物a/b对四种癌细胞(MCF-7, Bel-7402, A549及Hela)的抑制作用, 结果表明: 化合物a对MCF-7, Hela (IC₅₀值分别为: 120.2, 117.3 μmol·L^-1), 化合物b则对MCF-7, A549 (IC₅₀值分别为: 66.1, 72.4 μmol·L^-1)显示出比相同条件下5-Fu更好的抗癌抑制活性. 同时, 研究了a/b浓度﹑作用时间对癌细胞抑制率的影响.

关键词: 二氢化茚, 脱碳木脂素, 选择性, 抗癌抑制活性

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

引用此文

徐盈盈, 梁志武, 刘开建, 陈辉, 向建南. 酸催化α-细辛脑二聚反应及其产物抗癌活性研究[J]. 有机化学, 2013, 33(9): 1982-1987.

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.

导出引用 EndNote|Reference Manager|ProCite|BibTeX|RefWorks

分享此文

参考文献

[1] Moss, G. P. Pure Appl. Chem. 2000, 72, 1493.
[2] Van, T. T. T.; Van, C. P.; Houng, D. T. M.; Marc, L.; Françoise, G.; Pascal, R.; Van, H. N.; Van, M. C. J. Nat. Prod. 2012, 75, 1578.
[3] Qu, H. Y.; Ronald, L. M.; Dolores, J. T.; Richard, C. B.; Wang, W. Q. J. Nutr. 2005, 135, 598.
[4] Landete, J. M. Food Res. Int. 2012, 46, 410.
[5] Harald, W.; Marcel, S.; Zafar, Q.; Mark, L. Angew. Chem., Int. Ed. 2013, 52, 1.
[6] Yang, G. Y.; Wang, R. R.; Mu, H. X.; Li, Y. K.; Yang, L. M.; Zheng, Y. T.; Xiao, W. L.; Sun, H. D. J. Nat. Prod. 2013, 76, 250.
[7] Harmatha, J.; Dinan, L. Phytochem. Rev. 2003, 2, 321.
[8] Chen, C. Y.; Liaw, C. C.; Cheng, Y. B.; Lin, Y. C.; Chen, C. H.; Huang, Y. T.; Liou, S. S.; Chen, S. Y.; Chien, C. T.; Lee, G. C.; Shen, Y. C. Bioorg. Med. Chem. Lett. 2013, 3, 880.
[9] Liu, J. Y.; Cai, Y. Z.; Ricky, N. S. W.; Calvin, K. F. L.; Sydnry, C. W. T.; Stephen, C. W. S.; Tong, Y.; Zhang, Y. B. J. Agric. Food Chem. 2012, 60, 4067.
[10] Edlene, O. S.; Luciano, S. L.; Jorge, M. D.; Lidiane, C. M.; Maria, L. S. G.; Juceni, P. D. Nat. Prod. Res. 2011, 25, 2011.
[11] Yang, Y.; Dean, P.; Pan, S. F. J. Org. Chem. 2011, 76, 1902.
[12] Misra, R.; Pandey, R. C. J. Am. Chem. Soc. 1982, 104, 4478.
[13] David, R. A.; Matthew, A. J. D. Synth. Commun. 2001, 31, 2029.
[14] Esteban, A. U.; Beatriz, L.; Graciela, Y. M.; Albertina, G. M. Tetrahedron: Asymmetry 2009, 20, 1848.
[15] Rayabarapu, D. K.; Yang, C. H.; Cheng, C. H. J. Org. Chem. 2003, 68, 6726.
[16] Gao, H.; Katzenellenbogen, J. A.; Garg, R.; Hansch, C. Chem. Rev. 1999, 99, 723.
[17] Milton, J. R. J. Org. Chem. 1953, 18, 1701.
[18] Corson, B. B.; Julian, D.; Nickels, J. E.; Kutz, W. M.; Thayer, H. I. J. Org. Chem. 1954, 19, 17.
[19] Angel, B.; Avelino, C.; Hermenegildo, G.; Jaime, P. Appl. Catal. A: Gen. 1994, 116, 127.
[20] Elba, A.; Rosario, T.; Beatriz, L.; Magali, E.; Liliana, M. F.; Graciela, M.; José, M. A.; Ernesto, B. ARKIVOC 2003, x, 283.
[21] Wang, Z. C.; Jiang, L. S. Chin. J. Org. Chem. 1990, 10, 350 (in Chinese).
(王植材, 蒋腊生, 有机化学, 1990, 10, 350.)

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

PDF

可视化

摘要/Abstract

引用此文

分享此文

参考文献

相关文章 15

编辑推荐

相关统计

本文评价

[1]	付雅彤, 孙超凡, 张丹, 金成国, 陆居有. 巢式-碳硼烷硼氢键官能化反应研究进展[J]. 有机化学, 2024, 44(2): 438-447.
[2]	张剑, 梁万洁, 杨艺, 闫法超, 刘会. 联烯胺化合物的区域选择性双官能团化[J]. 有机化学, 2024, 44(2): 335-348.
[3]	陈宛婷, 钟雄威, 邢佳乐, 吴昌书, 高杨. C—N轴手性化合物的不对称催化合成研究进展[J]. 有机化学, 2024, 44(2): 349-377.
[4]	张莹珍, 江丹丹, 李娟华, 王菁菁, 刘昆明, 刘晋彪. 高选择性硒代半胱氨酸荧光探针的构建策略及成像[J]. 有机化学, 2024, 44(1): 41-53.
[5]	王婧怡, 刘金羽, 陈东升, 陈华燕, 谢欣, 南发俊. 新型选择性半胱氨酰白三烯受体1 (CysLT₁R)拮抗剂的设计合成及构效关系研究[J]. 有机化学, 2024, 44(1): 259-276.
[6]	张俊杰, 徐学涛. (S)-(–)-Xylopinine和(S)-(+)-Laudanosine的不对称合成[J]. 有机化学, 2023, 43(9): 3297-3303.
[7]	王兢睿, 冯永奎, 王能中, 黄年玉, 姚辉. 钯催化立体选择性合成硝基烷类β-碳糖苷[J]. 有机化学, 2023, 43(9): 3216-3225.
[8]	范威. O₂促进下五元环烯胺的C—H亚胺化[J]. 有机化学, 2023, 43(7): 2492-2498.
[9]	户晓兢, 郭斐翔, 朱润青, 周柄棋, 张涛, 房立真. 对烷氧基酚的合成及其去芳构化后的合成应用[J]. 有机化学, 2023, 43(6): 2239-2244.
[10]	蒋旺, 史壮志. 芳烃间/对位选择性碳氢硼化反应研究进展[J]. 有机化学, 2023, 43(5): 1691-1705.
[11]	纪健, 刘进华, 管丛, 陈绪文, 赵芸, 刘顺英. 原位生成的磺酸催化N-磺酰基-1,2,3-三氮唑与醇偶联高区域选择性合成N²-取代1,2,3-三氮唑[J]. 有机化学, 2023, 43(3): 1168-1176.
[12]	向勋, 何照林, 董秀琴. 钯和手性磷酸协同催化高效构建手性分子的研究进展[J]. 有机化学, 2023, 43(3): 791-808.
[13]	郭萍, 周勇, 赵杰. 多取代烯烃的Z∶E高选择性合成制备[J]. 有机化学, 2023, 43(3): 855-872.
[14]	戴春波, 夏思奇, 陈晓玉, 杨丽敏. 氮杂环卡宾(NHC)催化[4+3]环加成反应构建4-氨基苯并环庚烯内酯[J]. 有机化学, 2023, 43(3): 1084-1090.
[15]	沈梦涵, 李来强, 周泉, 王洁慧, 王磊. 可见光诱导下喹喔啉酮与吡咯衍生物的氧化偶联[J]. 有机化学, 2023, 43(2): 697-704.