有机化学 ›› 2017, Vol. 37 ›› Issue (3): 731-738.DOI: 10.6023/cjoc201610017 上一篇    下一篇

研究简报

异海松酰(胺)基硫脲类衍生物的合成及其生物活性评价

刘娟娟a, 卢言菊a,b, 王婧a,b, 毕良武a,b, 赵振东a,b   

  1. a 中国林业科学研究院林产化学工业研究所 生物质化学利用国家工程实验室 国家林业局林产化学工程重点开放性实验室 江苏省生物质能源与材料重点实验室 南京 210042;
    b 中国林业科学研究院林业新技术研究所 北京 100091
  • 收稿日期:2016-10-12 修回日期:2016-12-07 出版日期:2017-03-25 发布日期:2016-12-21
  • 通讯作者: 赵振东,E-mail:zdzhao@189.cn E-mail:zdzhao@189.cn
  • 基金资助:

    国家自然科学基金(No.31370575)资助项目.

Synthesis and Bioactivity Evaluation of Acylthiourea Derivatives Based on Isopimaric Acid

Liu Juanjuana, Lu Yanjua,b, Wang Jinga,b, Bi Liangwua,b, Zhao Zhendonga,b   

  1. a Institute of Chemical Industry of Forest Product, Chinese Academy of Forestry, National Engineering Laboratory for Biomass Chemical Utilization, Key and Open Laboratory on Forest Chemical Engineering State Forestry Adminstration, Key Laboratory of Biomass Energy and Material, Nanjing 210042;
    b Research Institute of Forestry New Technology, Chinese Academy of Forestry, Beijing 100091
  • Received:2016-10-12 Revised:2016-12-07 Online:2017-03-25 Published:2016-12-21
  • Contact: 10.6023/cjoc201610017 E-mail:zdzhao@189.cn
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No. 31370575).

为了开发具有较高生物活性的异海松酸类衍生物,将硫脲结构拼接到异海松酸骨架上,设计合成了15个未见报道的异海松酰(胺)基硫脲类化合物,其结构经FT-IR、1H NMR、13C NMR和HRMS或元素分析确证.对化合物进行了初步的抑菌和抗癌活性测试,大多数化合物对白色念珠菌表现出显著的抑制活性,且活性高于异海松酸.在浓度为100 μmol/L时,部分化合物对人黑色素瘤(A375)和前列腺癌(PC-3)癌细胞具有明显的增殖抑制作用,尤其化合物N-异海松酰基-N'-(3-甲基苯基)硫脲(3c)和N-异海松酰胺基-N'-(4-氟苯基)硫脲(6b)对癌细胞的抑制率达到90%以上.

关键词: 异海松酸, 酰基硫脲, 抑菌活性, 抗癌活性, 构效关系

To develop isopimaric acid derivatives with high bioactivity, fifteen acyl (amide) thiourea derivatives containing isopimaric acid skeleton were synthesized and confirmed by FT-IR, 1H NMR, 13C NMR and HRMS or elemental analysis. All the compounds were evaluated for their antibacterial and anticancer activity. Most of the compounds showed siginificant inhibitory activity which was higher than that of isopiamric acid against the Candida Albicans. At the concentration of 100 μmol/L, many compounds exhibited pronounced inhibitory effects on human melanoma cells (A375) and prostatic carcinoma (PC-3) cell lines, especially compounds N-isopimaric acyl-N'-(3-methylphenyl)sulfourea (3c) and N-isopimaric acylamino-N'-(4-fluorophenyl) sulfourea (6b) have the best anticancer activity, both with the inhibitory rate of over 90%.

Key words: isopimaric acid, acylthiourea, antibacterial activity, anticancer activity, structure-activity relationship