新型芥子醇衍生物、新木脂素及其含氮类似物的设计、合成及生物活性研究
摘要
天然产物结构和生物活性的多样性,使它在药物研究史上一直占据着非常重要的地位。以活性天然产物为先导化合物,对其进行合成或结构修饰是发现抗肿瘤药物的重要途径之一。苯丙素是自然界中一类分布十分广泛的天然产物,很多都具有重要的生物活性,本论文即是围绕苯丙素中两类重要的天然产物的结构改造而展开。
论文的第一部分阐述的是新型芥子醇类衍生物的设计与合成,以及对它们进行的细胞毒活性和构效关系研究,我们共合成了三个系列目标产物。第一系列是莲叶橐吾醇衍生物,我们以从莲叶橐吾(Ligularia nelumbifolia)中分离到的具有细胞毒活性的莲叶橐吾醇为先导化合物,共设计合成得到了四小系列目标化合物,分别为芥子酸乙酯类、芥子酸类、芥子醇类和芥子醛类化合物。对六株肿瘤细胞的体外生物活性测定显示部分目标化合物具有显著的细胞毒活性,它们的半数抑制浓度达到了10~(-6)M级别。根据活性测定结果,我们对这系列化合物进行了构效关系研究,并利用计算机模拟运算(CoMFA)分析,构建了一个初步的3D-QSAR模型,为进一步的药物设计提供指导。第二系列和第三系列则分别是芳环上单、双取代的芥子醇类衍生物及芥子醇共轭二烯类衍生物,这两系列化合物的相关生物活性评价正在进行中。
论文的第二部分是以姜黄素、咖啡酸苯乙酯等具有强抗肿瘤活性的新木脂素及其类似物为切入点,结合第一部分研究内容和结果,我们以不同取代的桂皮酸类衍生物与不同的芥子醇及取代的胺进行偶合,设计合成了三个系列新木脂素及其含氮类似物。它们分别是取代桂皮酸桂皮酯类化合物、苯丙烯酰胺类化合物和苯胺乙酰基苯丙烯酸酯类化合物。这三系列化合物的相关生物活性评价正在进行中。
Natural products play an important role in drug discovery for their structural and biological diversities. It's an important approach to develop new antitumor agents by synthesis and structural modification of the active natural product as the lead compound. Phenylpropanoids, widespread in nature, have broad and interesting bioactivies and this thesis is carried out on two kinds of natural phenylpropanoids.
The first part of the thesis is design, synthesis and SAR of new sinapyl alcohol derivatives and its analogues including three series of compounds. We have the first serie as sinapyl alcohol derivatives with 7-geranyl sinapyl alcohol as our lead compound isolated from Ligularia nelumbifolia. Four kinds of derivatives including substituted sinapic acid ethyl esters, sinapic acids, sinapyl alcohols and sinapyl aldehydes were synthesized and subjected to six human tumor cell lines screening. The results indicate that some of the synthetic compounds possess remakable cytotoxicties on selected tumor cell lines with IC_(50) values at 10~(-6) M scale. With the cytotoxicitic results, SAR studies were performed and a 3D-QSAR model was built by the preliminary CoMFA molecular-modelling study, which could be a guide for further drug design. Another two series of compounds as mono-, double- substituted sinapl alcohols and the conjugated diene derivatives were also synthesized and their biological activities assay is still in progress.
The second part is based on our former research results and reported curcumin and caffeic acid phenylester, the representative of cytotoxic neolignans. Three series of neolignans and its nitrogen-containing analogues were designed and synthesized by coupling the two parts of substitutied sinapic acids and subsititued sinapyl alcohols or substituted amines. The three series are distinguished as substituted sinapic acid sinapyl esters, substituted cinnamamide derivatives and phenylamine acetyl sinapic acid ester derivatives and their biological activities assay is still in progress.
论文的第一部分阐述的是新型芥子醇类衍生物的设计与合成,以及对它们进行的细胞毒活性和构效关系研究,我们共合成了三个系列目标产物。第一系列是莲叶橐吾醇衍生物,我们以从莲叶橐吾(Ligularia nelumbifolia)中分离到的具有细胞毒活性的莲叶橐吾醇为先导化合物,共设计合成得到了四小系列目标化合物,分别为芥子酸乙酯类、芥子酸类、芥子醇类和芥子醛类化合物。对六株肿瘤细胞的体外生物活性测定显示部分目标化合物具有显著的细胞毒活性,它们的半数抑制浓度达到了10~(-6)M级别。根据活性测定结果,我们对这系列化合物进行了构效关系研究,并利用计算机模拟运算(CoMFA)分析,构建了一个初步的3D-QSAR模型,为进一步的药物设计提供指导。第二系列和第三系列则分别是芳环上单、双取代的芥子醇类衍生物及芥子醇共轭二烯类衍生物,这两系列化合物的相关生物活性评价正在进行中。
论文的第二部分是以姜黄素、咖啡酸苯乙酯等具有强抗肿瘤活性的新木脂素及其类似物为切入点,结合第一部分研究内容和结果,我们以不同取代的桂皮酸类衍生物与不同的芥子醇及取代的胺进行偶合,设计合成了三个系列新木脂素及其含氮类似物。它们分别是取代桂皮酸桂皮酯类化合物、苯丙烯酰胺类化合物和苯胺乙酰基苯丙烯酸酯类化合物。这三系列化合物的相关生物活性评价正在进行中。
Natural products play an important role in drug discovery for their structural and biological diversities. It's an important approach to develop new antitumor agents by synthesis and structural modification of the active natural product as the lead compound. Phenylpropanoids, widespread in nature, have broad and interesting bioactivies and this thesis is carried out on two kinds of natural phenylpropanoids.
The first part of the thesis is design, synthesis and SAR of new sinapyl alcohol derivatives and its analogues including three series of compounds. We have the first serie as sinapyl alcohol derivatives with 7-geranyl sinapyl alcohol as our lead compound isolated from Ligularia nelumbifolia. Four kinds of derivatives including substituted sinapic acid ethyl esters, sinapic acids, sinapyl alcohols and sinapyl aldehydes were synthesized and subjected to six human tumor cell lines screening. The results indicate that some of the synthetic compounds possess remakable cytotoxicties on selected tumor cell lines with IC_(50) values at 10~(-6) M scale. With the cytotoxicitic results, SAR studies were performed and a 3D-QSAR model was built by the preliminary CoMFA molecular-modelling study, which could be a guide for further drug design. Another two series of compounds as mono-, double- substituted sinapl alcohols and the conjugated diene derivatives were also synthesized and their biological activities assay is still in progress.
The second part is based on our former research results and reported curcumin and caffeic acid phenylester, the representative of cytotoxic neolignans. Three series of neolignans and its nitrogen-containing analogues were designed and synthesized by coupling the two parts of substitutied sinapic acids and subsititued sinapyl alcohols or substituted amines. The three series are distinguished as substituted sinapic acid sinapyl esters, substituted cinnamamide derivatives and phenylamine acetyl sinapic acid ester derivatives and their biological activities assay is still in progress.
引文
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