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2012 , Vol. 32 >Issue 9: 1753 - 1758

DOI: https://doi.org/10.6023/cjoc1201071

研究简报

新型龙胆酸衍生物的合成及其抑制酪氨酸酶活性研究

  • 宋长伟 ,
  • 熊丽丹 ,
  • 王裕军 ,
  • 张南 ,
  • 李霞 ,
  • 李颖 ,
  • 李利 ,
  • 尹述凡
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  • a 四川大学化学学院 成都 610064;
    b 四川省化妆品工程技术研究中心 成都 610064;
    c 四川大学华西医院皮肤科 成都 610041

收稿日期: 2012-01-07

  修回日期: 2012-05-11

  网络出版日期: 2012-03-14

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Synthesis and Inhibition of Tyrosinase Acitivity of New Gentisic Acid Derivatives

  • Song Changwei ,
  • Xiong Lidan ,
  • Wang Yujun ,
  • Zhang Nan ,
  • Li Xia ,
  • Li Ying ,
  • Li Li ,
  • Yin Shufan
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  • a College of Chemistry, Sichuan University, Chengdu 610064;
    b Sichuan Province Cosmetics Engineering Technology Research Center, Chengdu 610064;
    c West China Hospital, Sichuan University, Dermatological Department, Chengdu 610041

Received date: 2012-01-07

  Revised date: 2012-05-11

  Online published: 2012-03-14

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摘要

为发现新型的美白活性化合物,以龙胆酸甲酯、卤代烃和α-羟基酸乙酯为原料,合成了10个未见文献报道的2-羟基-5-烷(H)氧基苯甲酸酯类衍生物(3a,3b和6a～6h),其结构经1H NMR,IR,MS和HRMS确认.初步生物活性测试结果表明6a,6b,6e和6f具有较强的抑制酪氨酸酶活性,进一步药理实验表明经取代改造后的6a～6h,其毒性和光学毒性都相对龙胆酸甲酯和氢醌更低.

关键词： 美白; 龙胆酸甲酯; 酪氨酸酶; 毒性; 光学毒性

本文引用格式

宋长伟 , 熊丽丹 , 王裕军 , 张南 , 李霞 , 李颖 , 李利 , 尹述凡 . 新型龙胆酸衍生物的合成及其抑制酪氨酸酶活性研究[J]. 有机化学, 2012 , 32(9) : 1753 -1758 . DOI: 10.6023/cjoc1201071

Abstract

To discover new whitening active compounds, ten novel 2-hydroxy-5-alkyl(H)oxybenzoic ester derivatives (3a, 3b and 6a～6h) were prepared via the starting materials of methyl gentisate, alkyl halides and α-hydroxy acid ethyl ester. Their chemical structures were confirmed by 1H NMR, IR, MS and HRMS techniques. The preliminary bioassay test demonstrated that compounds 6a, 6b, 6e and 6f had stronger inhibition of tyrosinase activity. Further pharmacological experiments showed that after substitution modification of compounds 6a～6h, their toxicity and phototoxicity are lower than methyl gentisate and hydroquinone.

Key words： white; gentian methyl; tyrosinase; toxicity; optical toxicity

参考文献

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