【作者】 刘珀润；

【导师】 徐石海；

【作者基本信息】 暨南大学 ， 分析化学， 2006， 硕士

【摘要】 Aldisin和Fuseain是从中国南海海洋生物海绵中分离得到的五元杂环（吡咯、呋喃）并内酰胺化合物。Aldisin和Fuscain及其合成中间体都具有一定的生物活性，主要表现在治疗心血管疾病与抗肿瘤活性。本文分别以吡咯和2-呋喃甲酸为原料，经过多步反应，合成了目标产物Aldisin、及溴代衍生物3-Bromoaldisin、2，3-Dibromoaldisin和合成了系列Fuscain的中间体N-（2-呋喃甲酰基）-氨基酸。本论文分为两部分。 第一部分，通过对具有抗脂质过氧化作用的天然物质Aldisin及衍生物的分离、活性、合成报道的综述和分析，在本课题组的合成路线基础上作了改动和优化，经过3步主反应，大量合成了9个中间产物，最后以质量比为1：10的P₂O₅／CH₃SO₃H为关环剂更有效地合成了Aldisin及两个溴代衍生物，通过HPLC跟踪手段提高了关环反应的可操作性和效率，收率61.2～73.1％，提高了8.7～15.7％。 第二部分，根据另一种未有文献报道其全合成的活性五元杂环呋喃并内酰胺化合物Fuscain的物化特性及活性研究现状，设计合成路线，合成了10个Fuscain类化合物的合成中间体：N-（2-呋喃甲酰基）．氨基酸甲酯和其水解产物N-（2-呋喃甲酰基）-氨基酸，收率89.6～93.3％，为进一步全合成目标产物提供了原料，并对部分产物作了活性实验。 在研究工作中，合成产物均通过重结晶或色谱技术分离纯化，用NMR、IR，部分通过MS、X-ray射线单晶衍射分析等现代分析测试手段，进行结构鉴定。更多还原

【Abstract】 Aldisin and Fuscain, are seven-member lactam compounds isolated from the marine sponge collected from the South China Sea.The compounds themselves and their derivatives show moderate cardiovascular and antitumor bioactivities in vitro.The thesis describe the syntheses of Aldisin, Bromoaldisin,and the intermiediates of Fuscain,N-(funan-2-carbonyl)-ammio acid by multi-step reactions with the economic and convenient compounds of pyrrole and furan-2-carboxylic acid as starting materials.The result of the thesis show a way to a better understanding about the syntheses and the structure-activity relationship of heteroatomic seven-member lactam natural products.There are two parts of the thesis.In Part One,the research on the isolations,bioactivities and syntheses of the Aldisin derivatives which show antilipoperoxidation activities were reviewed. Based on the previous route, the scheme was adapted and optimized.Aldisin and the bromated derivatives were synthesized in greater yields via cyclodehydration in reagent composed of a 1 :10 solution by weight of phosphorus pentoxide in methane -sulfonic acid. HPLC monitoring was conducted to enhance the efficiency.The Aldisin derivatives were obtained in 61.2～73.1% yield, 8.7～15.7% elevated, in the reaction with phosphorus pentoxide in methanesulfonic acid.In Part Two,the scheme to synthesize another lactam Fuscain was proposed on fully consideration of the physical-chemical traits,survey of activities and syntheses.5 intermiediates, N-(funan-2-carbonyl)-ammio acid methyl esters,were obtained, followed by the hydrolyzation to corresponding N-(funan-2-carbonyl)-ammio acid in 89.6～93.3% yields.Bioactivities of a part of them were analysed subsequently.In both two Parts,all of the synthetic products were purified by recrystallyzation or chromatography .NMR,IR, MS or X-ray diffraction analyse and some other modern means for analysis were appealed to determine the structures,and physical-chemical properties.更多还原