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Chinese Journal of Organic Chemistry >

2013 , Vol. 33 >Issue 9: 1982 - 1987

DOI: https://doi.org/10.6023/cjoc201303030

Notes

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

  • Xu Yingying ,
  • Liang Zhiwu ,
  • Liu Kaijian ,
  • Chen Hui ,
  • Xiang Jiannan
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  • a College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082;
    b School of Biology, Hunan University, Changsha 410082

Received date: 2013-03-19

  Revised date: 2013-05-23

  Online 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)

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Abstract

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

Cite this article

Xu Yingying , Liang Zhiwu , Liu Kaijian , Chen Hui , Xiang Jiannan . Acid-Catalyzed Dimerization of α-Asarone and Anticancer Evaluation of the Dimers[J]. Chinese Journal of Organic Chemistry, 2013 , 33(9) : 1982 -1987 . DOI: 10.6023/cjoc201303030

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