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木脂素是在自然界中广泛存在的一类天然产物，它不仅可以在众多的植物中找到，在动物体乃至人体中也有发现。许多木脂素类的化合物都表现有很强的生物活性，常常是一些潜在的药物.因此，关于木脂素的研究工作得到了各方面的广泛关注。芳基四氢萘类木脂素中的鬼臼毒素具有显著的抗肿瘤活性，其中鬼臼毒素的糖苷衍生物etoposide(VP-16)和teniposide (VM-26)被广泛用于临床。因此，研究鬼臼毒素中间体的合成方法具有重要的学术价值和应用价值。 论文主要分为综述和实验两部分。首先在综述部分系统的概述了以下内容： 1)鬼臼毒素类生物活性物质研究概况。鬼臼毒素主要存在于小檗科多年生草本类群鬼臼亚科八角莲属、桃儿七属、山荷叶属及足叶草属植物中。鬼臼毒素及其衍生物具有显著具有很好的生物活性，其糖苷衍生物是临床使用广泛的抗肿瘤药物。由于鬼臼毒素结构复杂，其合成路线普遍存在路线长，产率低等缺点。从植物中提取仍是目前获得鬼臼毒素的主要途径.因此，对鬼臼毒素的合成研究具有重要的应用价值。 2)鬼臼毒素的骨架构筑策略和近年来研究进展。大多合成主要依靠几个关键途径来构建鬼臼毒素的C-18骨架。如Diels-Alder 反应，串联共轭加成反应等。近年来对鬼臼毒素的研究主要集中在中间体合成工艺的改进和新合成路线的探索两方面。 论文实验部分我们在综合考虑文献的基础上，经过实验摸索，并结合鬼臼毒素中间体的结构特点以简单的胡椒醛为起始原料，对α,β-不饱和羰基化合物具有选择性还原的锂铝氢还原反应为关键步骤，先后经过Knoevenagel缩合，间氯过氧苯甲酸环氧化，碱性过氧化氢环氧化，DCC缩合酯化等反应合成了3个鬼臼毒素中间体。由此中间体可比较方便地合成鬼臼毒素。 |
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3楼2008-04-19 15:37:24
xiongwei3707
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Lignans in nature is the widespread presence of a class of natural products, which not only can be found in many plants, animals and even humans have found. Lignans many compounds have shown a strong biological activity, and often is some potential drugs. Therefore, the lignans work on various aspects of the wide concern. Aryl tetralin of lignans in podophyllotoxin has significant anti-tumor activity, which podophyllotoxin glucoside derivatives etoposide (VP-16) and teniposide (VM-26) is widely used in clinical. Therefore, the study podophyllotoxin intermediate synthesis method has an important academic value and application value. Summary of main thesis is divided into two parts and experiment. In the first part of the system outlined in the following: 1) podophyllotoxin category bioactive substances Research. Podophyllotoxin exists primarily on the Berberidaceae perennial herb group podophyllotoxin Bajiaolian a subfamily, Sinopodophyllum emodi a mountain of leaves and grass is a foot of the plants. Podophyllotoxin and its derivatives are very good with significant biological activity, its clinical glucoside derivatives are widely used anticancer drug. As podophyllotoxin complex structures, and its long line of synthetic route widespread, low-yield shortcomings. Extracted from the plant was still is the primary means of podophyllotoxin. Therefore, the synthesis of podophyllotoxin has an important value. 2) podophyllotoxin strategy and the framework to build on the progress in recent years. Most rely mainly on the synthesis of several key ways to build podophyllotoxin C-18 frame. If Diels-Alder reaction, Tandem conjugate addition reaction. In recent years the study of podophyllotoxin mainly concentrated in the intermediate and Improved synthesis of new synthetic routes to explore two aspects. Papers in the experimental part of our literature considered on the basis of the experimental exploration, and podophyllotoxin intermediates with the structural characteristics of a simple pepper aldehyde as the starting material, α, β-unsaturated carbonyl compounds are selective reduction lithium aluminum hydrogen reduction reaction as the key steps to have the Knoevenagel condensation, peracetic acid epoxy between chlorine and alkaline hydrogen peroxide epoxy, DCC condensation esterification reaction of the three podophyllotoxin intermediates. This intermediates can be more convenient synthesis of podophyllotoxin. |
2楼2008-04-18 11:36:59