高等学校化学学报

高等学校化学学报 ›› 2010, Vol. 31 ›› Issue (12): 2400.

• 研究论文 • 上一篇    下一篇

辣椒碱类似物的合成、结构及抗肿瘤活性

汪文龙,黄燕兰,胡惟孝,单尚   

  1. 浙江工业大学化学工程与材料学院,  杭州 310014
  • 收稿日期:2010-03-01 修回日期:2010-05-24 出版日期:2010-12-10 发布日期:2010-12-06
  • 通讯作者: 单尚 E-mail:shanshang@mail.hz.zj.cn
  • 作者简介:单尚, 男, 博士, 教授, 主要从事有机化合物的合成与结构的研究. E-mail: shanshang@mail.hz.zj.cn
  • 基金资助:

    浙江省自然科学基金(批准号:  M203027)资助.

Synthesis,Structures and Anti-tumor Properties of Capsaicin Analogues

WANG Wen-Long, HUANG Yan-Lan, HU Wei-Xiao, SHAN Shang*   

  1. College of Chemical Engineering and Materials,  Zhejiang University of Technology,  Hangzhou 310014, China
  • Received:2010-03-01 Revised:2010-05-24 Online:2010-12-10 Published:2010-12-06
  • Contact: SHAN Shang E-mail:shanshang@mail.hz.zj.cn
  • About author:单尚, 男, 博士, 教授, 主要从事有机化合物的合成与结构的研究. E-mail: shanshang@mail.hz.zj.cn
  • Supported by:

    浙江省自然科学基金(批准号:  M203027)资助.

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被引次数

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摘要： 以自制或试剂级羧酸、酰氯为原料，通过酰氯化、胺基化反应，设计合成了15个含香兰素胺的酰胺结构的辣椒碱类似物。其结构经IR,MS,1HNMR表征,并用X射线单晶衍射测定了化合物W5和W11的晶体结构。体外抗肿瘤活性测试表明，该类化合物具有一定程度的抗肿瘤活性。化合物W1在100μg/ml时，对人宫颈癌细胞（HELA）、人肝癌细胞（SMMC-7721）、人口腔表皮癌细胞（KB）、人卵巢癌细胞（HO-8901）抑制率均达到90%以上。W13在100μg/ml时，对KB、HO-8901抑制率分别达到89.62%、90.36%。初步构效关系分析认为，含香兰素胺的酰胺结构片段为一活性基团。

关键词: 辣椒碱类似物, 香兰素胺, 抗肿瘤活性, 构效关系

Abstract: Capsaicin is a natural product existing in the fruit of capsicum, which has been used for centuries for its medical effects. Modern research showed that capsaicin exhibits anti-proliferative activities against tumor cells. For the reason of studying the structure-activity relationship of capsaicin molecule, fifteen capsaicin analogues comprising the segment of vanillylamine acylamide were designed and synthesized from carboxylic acid or acyl chloride via the acylation and amidogen reactions. Their structures were characterized by IR, MS and 1H NMR techniques. The crystal structures of compounds W5 and W11 were determined by X-ray diffraction analysis. The anti-tumor properties of capsaicin analogues were evaluated against four different tumor cell lines by an MTT assay. The results suggest that the vanillylamine acylamide-containing compounds exhibit anti-proliferative activities against selected tumor cells. The inhibition rates against HELA , SMMC-7721, KB and HO-8901 of compound W1 have all reached greater than 90 % at the concentration of 100 μg/mL. The inhibition rates against KB and HO-8901 of compound W13 have respectively reached 89.62 % and 90.36 % at the concentration of 100 μg/mL. Preliminary structure-activity relationship analysis indicates that the segment of vanillylamine acylamide is an active group in anti-tumor process.

Key words: capsaicin analogue, vanillylamine, anticancer activity, structure-activity relationship

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