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Chinese Journal of Organic Chemistry >

2020 , Vol. 40 >Issue 6: 1578 - 1587

DOI: https://doi.org/10.6023/cjoc202001016

Synthesis and Anti-tumor Activity of Novel Garcinol Analogs

  • Zhou Huiyuan ,
  • Wu Yanlin ,
  • Huang Dianhong ,
  • Zhang Mingting ,
  • Chen Huanming ,
  • Qian Mingcheng ,
  • Zhao Shuai ,
  • Zhang Xinyan ,
  • Chen Xin
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  • a School of Pharmaceutical Engineering and Life Science, Changzhou University, Changzhou, Jiangsu 213164;
    b Beijing Institute of Dental Research, Beijing Stomatological Hospital, Capital Medical University, Beijing 100050

Received date: 2020-01-09

  Revised date: 2020-03-09

  Online published: 2020-04-10

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 21272029, 81772868).

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Abstract

Garcinol possesses a wide range of biological activities, such as anti-inflammation, anti-tumors, anti-oxidation, induction of apoptosis and so on. In this paper, the modification of the side chains in garcinol was carried out to enhance its anti-tumor activity. Employing acetylacetone as starting material, three new analogs of garcinol were prepared by means of Michael addition, Knoevenagel condensation, and so on. Furthemore, their biological activity was assessed by methyl thiazolyl tetrazolium (MTT) method and the structure-activity relationship was analyzed. The results showed that the inhibitory activities of the three new analogs on oral squamous cell carcinoma were moderately lower than that of garcinol. Hence, the isoprenyl group at the C4 position and the allylic group at the C8 position might play vital roles for the biological activity of garcinol.

Key words： garcinol; structural modification; Michael addition; anti-tumor

Cite this article

Zhou Huiyuan , Wu Yanlin , Huang Dianhong , Zhang Mingting , Chen Huanming , Qian Mingcheng , Zhao Shuai , Zhang Xinyan , Chen Xin . Synthesis and Anti-tumor Activity of Novel Garcinol Analogs[J]. Chinese Journal of Organic Chemistry, 2020 , 40(6) : 1578 -1587 . DOI: 10.6023/cjoc202001016

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