Synthesis,Structures and Anti-tumor Properties of Capsaicin Analogues

Chem. J. Chinese Universities ›› 2010, Vol. 31 ›› Issue (12): 2400.

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Synthesis,Structures and Anti-tumor Properties of Capsaicin Analogues

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

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.

Abstract

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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WANG Wen-Long, HUANG Yan-Lan, HU Wei-Xiao, SHAN Shang. Synthesis,Structures and Anti-tumor Properties of Capsaicin Analogues[J]. Chem. J. Chinese Universities, 2010, 31(12): 2400.

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Synthesis,Structures and Anti-tumor Properties of Capsaicin Analogues

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