摘要
[目的]设计合成一系列由紫檀芪和肉桂酸衍生物拼合而成的新化合物,并检测其抗癌活性.[方法]以3,5-二羟基苯甲酸为原料,经过甲基化、还原、溴代、Witting-Horner等反应合成紫檀芪;以取代苯甲醛和丙二酸为原料,经过knoevenagel反应合成肉桂酸衍生物;将紫檀芪和肉桂酸衍生物拼合成新化合物,其结构经1 H-NMR确认,在HeLa,HCT116,BEL-7402及L-02等细胞株中采用MTT法测定新化合物抑制细胞增殖的效应以判断其抗癌活性.[结果]在HeLa,HCT116,BEL-7402及L-02细胞株中,紫檀芪与肉桂酸衍生物拼合而成的7种新化合物抑制细胞增殖的能力均较弱,不具有抗肿瘤的潜力.[结论]紫檀芪结构上的酚羟基和肉桂酸结构中的羧基等极性基团均被掩蔽时,化合物的脂水分配系数过高影响化合物通过细胞膜而无法起到抗癌作用.
OBJECTIVE To design and synthesize a series of hybrid formed from pterostilbene and cinnamic acid derivatives,and detect its upgraded antitumor activity.METHODS Using 3,5-dihydroxybenzoic acid as a starting material to synthesize pterostilbene by a series of reaction such as methylation,reduction,bromination,Witting-Horner Reaction,etc.,and a series of cinnamic acid derivative were synthesized by Knoevenagel Reaction as the substituted benzaldehydes and malonic acid as the starting materials.And then,combining the structural feature of pterostilbene and cinnamic acid derivatives each other to synthesized novel compounds according to the association principle of pharmaceutical chemistry.All compounds were confirmed by 1 H NMR and the growth inhibitory activities in vitro were evaluated by MTT assay in some cell lines such as HeLa,HCT116,BEL-7402 and L-02,etc.RESULTSThe seven hybrids composed from pterostilbene and cinnamic acid derivatives all expressed no significant anti-proliferation activities in the four kinds cell line.CONCLUSION When the polar groups as well as phenolic hydroxyl group of pterostilbene and carboxyl group of cinnamic acid derivatives,the lipid-water partition coefficient is increased excessively that compound couldnt pass through the cell wall to express antitumor activity.
出处
《延边大学医学学报》
CAS
2015年第4期298-300,共3页
Journal of Medical Science Yanbian University
基金
国家自然科学基金(No.81260226)
关键词
紫檀芪
肉桂酸
MTT法
抗肿瘤活性
pterostilbene
cinnamic acid
MTT assay
anti-tumor activity
