Pictet–Spengler反应论文β-咔啉类生物碱的合成及其生物活性.docVIP

Pictet–Spengler反应论文：β-咔啉类生物碱的合成及其生物活性 【中文摘要】β-咔啉类生物碱,是吲哚类生物碱中非常重要的一类,它是由吲哚并吡啶构成的三环体系,结构简单,数量众多。主要分布于植物、海洋生物、蓝藻、蘑菇、动物（如非洲蛙）,甚至人体的组织、血液中。这类生物碱种类繁多,生物活性广泛,如抗肿瘤活性、杀虫活性、抑菌活性、抗氧化活性、抗病毒活性、抗抑郁活性等等。本文主要根据β-咔啉生物碱在人体的代谢途径,分为两条路线来进行目标产物合成。主要的研究结果如下:1.路线一,以吲哚-3-甲醛为原料,通过Henry反应（超声波辅助）、LiAlH4 【英文摘要】β-Carboline and its derivatives show great significance to our life, because of their importance in natural product and broad bioactive activities such as antitumor, bacteriostasis, anti- oxidation, antiviral,antidepressant and so on.In this paper,we used three compounds as starting material by two routes,then got 20 compounds.the compounds were identified and evaluated on anti-bacterial activity , insecticidalactivity and antitumor activity.The results were just as follows.(1). Route 1, with Indoles - 3– formaldehyde as starting material, through Henry reaction followed by deoxidation of LiAlH4, we got tryptamine, which was reacted with methanal and aldehyde, leading to tetrahydro -β-Carbolines.then through a dehydrogenation, compounds a-1and a-2 were gotten.(2). Route 1, we got compounds a-13, a-14, a-15,a-16,a-17 and a- 20 through Pictet–Spengler reaction with 5-Methoxy tryptamine reacted with methanal,aldehyde,propionaldehyde,butanal,isobutanal, benzaldehyde.(3) .Route 2 , a Pictet–Spengler reaction between tryptophan and Methanal,aldehyde,propionaldehyde , butanal , isobutanal , benzaldehyde, m-nitrobenzaldehyde, o-nitrobenzaldehyde, anisaldehyde, 3-methoxy-4-hydroxybenzaldehyde, o-hydroxybenzaldehyde, acetone, cyclohexanone, then through a dehydrog enation, we got compounds a-1—a-12, a-18 and a-19.(4). All the compounds’Structures were elucidated mainly based on 1~HNMR, (13)~CNMR, DEPT and ESI-MS. In those compounds,there are 7 compounds(a-5、a-10、a-11、a-15、a-16、a-17 and a-19) were new.(5). Anti-bacterial activity in vitro against staphylococcus aureus, Bacillus cereus, Bacillus subtilis, Pseudomonas aeruginosa and Esch