Syntheses Of Aldisin's Derivatives And Intermiediates Of Fuscain

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.