黄酮类化合物的合成研究-药物化学专业毕业论文.docxVIP

浙 浙 江 大 学． 博士后 研 究 工 作报告 STUDIES ON THE SYNTHESIS OF FLAVONOIDS Abstract Flavonoids are me most important class of polyphenolic secondary metabolites in plant．They generally display a chromophore of the 2-phenyl—l— benzopyran type diversely substitued by OH and Ome groups，which include flavones，flavanones，flavonols，chalcone，biflavonoids，and further modification of the chromophore(O—and C—glycosidation)．Besides their important biological roles in plant pigmentation，nitrogen fixation and chemical defense，flavonoids possess anti—cancer，anti—rival，anti-inflammatory，etc．properties．However．1inle information iS SO far availble on the structure and activity relationship．or the synthetic methods for large scale．In this work，we are to investigate the synthetic method for flavonoida，tO abrain some series of fiavonoids for biological studies． Here，after much effort we found a new route for synthesis of flavones．The route started from aniline，via bromination，deamination，actylation，consendation and hydroxylation，and led to abtain a series of flavone compounds，including 22 (a，b，e，e，f)．This route is cheap，safe and little pollution superier to the traditional ones．It is not found to be reported elsewhere． Later，we chose the 1，3,5一trimethoxyl bezene for materia，via acytylation， demethylation and condensation with m—halo·substituted benzenaldehyde，to have got a series of m—halo—substituted chaJcone(24：a，b，e，d)，and further isomerate to get a series of 3-halo一5，7-dimethoxyl—fiavanones(25：a，b，c，d)．They all are potential medicine， Finally，on the basis of the synthesized flavonoids，we investigated the couping reaction between them to synthesize the strong biological activity substance biflavonoids．Thus，catalysed by Pd(OAc)2／n—Bu4NBr， 3-I．5，7一 dimethoxyl—flavanones coupling itselfe to get tWO new biflavonoids 27 and 28． The investigation is carried on in our lab．All related IR，1HNMR and MS are line with the compound’S chemical structure． 4 浙 浙 江 大 学 博士 后研究工作报 告 前言 黄酮类化合物(flavonids)广泛地存