桦木酮酸缩氨基硫脲及其过渡金属络合物的合成与表征

发布时间：2018-01-09 22:11

本文关键词：桦木酮酸缩氨基硫脲及其过渡金属络合物的合成与表征　出处：《延边大学》2017年硕士论文　论文类型：学位论文

【摘要】：白桦脂酸,是一种羽扇烷类五环三萜烯类化合物,研究表明桦木酸无毒,并被证明具有多种药理作用,如抗菌,抗疟疾,抗癌,抗HIV病毒等。桦木酸对多种癌细胞具有细胞毒性,如肺癌,卵巢癌,宫颈癌等。在众多领域里有着十分广泛研发前景,极具研发潜力。缩氨基硫脲基团是酮或者醛类化合物在不同的反应条件或溶剂况下,与硫代氨基脲脱水缩合而形成的一类特殊的希夫碱,缩氨基硫脲衍生物所形成的的双环螯合物对金属电子有约束力,可作为药效基团对某些氨基酸蛋白质发挥监管作用。研究表明:缩氨基硫脲金属络合物活性要优于其相应的配体。故而,本文在桦木酸骨架中引入缩氨基硫脲基团,后与多种无机过渡金属盐进行络合,以寻找活性更为优良的化合物。本文以桦木醇为起始物,直接氧化合成桦木酮酸,引入羰基基团,羧基上的氢键给体提高了对肿瘤细胞的靴向作用,对活性有所贡献,并且加强了药物的溶解性,最后在C-3侧链上引入氨基硫脲,合成桦木酮酸氨基硫脲化合物,并以此为配体,与多种金属盐反应得到一系列的配体;2种配体与Pd(dmso)2Cl2反应得2种钯金属配合物。对合成的6种配合物,利用了 IR,TOF-MS,1H-NMR,Elemental analysis和TGA等证明了其配位模式。最后对所合成的配体及其4种金属配合物进行了抗菌实验以及癌细胞增殖实验。结果显示,配体及其4种金属络合物的抗菌效果并不理想;而Ag(L1)2Cl·H2O和Cu(L1)2Br2具有抑制人源乳腺癌细胞的细胞增殖能力;Cu(L1)LBr2对Hela细胞具有一定的抑制能力。其IC50值在10-20μM之间。
[Abstract]:Bai Hua, a pentacyclic triterpene compound, has shown that betulinic acid is nontoxic and has been shown to have many pharmacological effects, such as antimicrobial, antimalarial and anticancer activities. Betulinic acid has cytotoxicity to many kinds of cancer cells, such as lung cancer, ovarian cancer, cervical cancer and so on. The thiosemicarbazone group is a special Schiff base formed by dehydration and condensation of ketone or aldehydes with thiosemicarbazone under different reaction conditions or solvent conditions. The bicyclic chelates formed by thiosemicarbazone derivatives are binding on metal electrons. It can be used as the effective group to supervise some amino acid proteins. The results show that the activity of thiosemicarbazone metal complex is better than its corresponding ligand. In this paper, thiosemicarbazone group was introduced into the betulinic acid skeleton and then complexed with a variety of inorganic transition metal salts in order to find more active compounds. In this paper, betulinol was used as the starting material. Direct oxidation of birch ketonic acid, the introduction of carbonyl groups, carboxyl hydrogen bond donor enhanced the boot on tumor cells, contributed to the activity, and enhanced the solubility of drugs. Finally, thiosemicarbazide was introduced into C-3 side chain to synthesize betulinone acid thiosemicarbazone compounds, and a series of ligands were obtained by reaction with various metal salts. Two palladium metal complexes were synthesized by the reaction of two ligands with Pd(dmso)2Cl2. Elemental. Analysis and TGA proved their coordination pattern. Finally, the synthesized ligands and their four metal complexes were tested for antibacterial and cancer cell proliferation. The antibacterial effect of ligands and their four metal complexes is not ideal. Ag(L1)2Cl 路H2O and Cu(L1)2Br2 could inhibit the proliferation of human breast cancer cells. Cu(L1)LBr2 had a certain inhibitory effect on Hela cells, and its IC50 value ranged from 10 to 20 渭 M.
【学位授予单位】：延边大学
【学位级别】：硕士
【学位授予年份】：2017
【分类号】：O641.4

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