Pictet–Spengler反應(yīng)論文：β-咔啉類生物堿的合成及其生物活性

1、 pictetspengler反應(yīng)論文：-咔啉類生物堿的合成及其生物活性【中文摘要】-咔啉類生物堿,是吲哚類生物堿中非常重要的一類,它是由吲哚并吡啶構(gòu)成的三環(huán)體系,結(jié)構(gòu)簡單,數(shù)量眾多。主要分布于植物、海洋生物、藍藻、蘑菇、動物（如非洲蛙）,甚至人體的組織、血液中。這類生物堿種類繁多,生物活性廣泛,如抗腫瘤活性、殺蟲活性、抑菌活性、抗氧化活性、抗病毒活性、抗抑郁活性等等。本文主要根據(jù)-咔啉生物堿在人體的代謝途徑,分為兩條路線來進行目標產(chǎn)物合成。主要的研究結(jié)果如下:1.路線一,以吲哚-3-甲醛為原料,通過henry反應(yīng)（超聲波輔助）、lialh4【英文摘要】-carboline and its d

2、erivatives 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 co

3、mpounds.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,

4、 which was reacted with methanal and aldehyde, leading to tetrahydro -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 pictetspengler reaction with 5-methoxy tryptamine reacted with methanal,aldehy

5、de,propionaldehyde,butanal,isobutanal, benzaldehyde.(3) .route 2 , a pictetspengler reaction between tryptophan and methanal,aldehyde,propionaldehyde , butanal , isobutanal , benzaldehyde, m-nitrobenzaldehyde, o-nitrobenzaldehyde, anisaldehyde, 3-methoxy-4-hydroxybenzaldehyde, o-hydroxybenzaldehyde,

6、 acetone, cyclohexanone, then through a dehydrog enation, we got compounds a-1a-12, a-18 and a-19.(4). all the compoundsstructures were elucidated mainly based on 1hnmr, (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-bact

7、erial activity in vitro against staphylococcus aureus, bacillus cereus, bacillus subtilis, pseudomonas aeruginosa and escherichia coli of compounds a-1a-12、a-18 and a-19 by tablet diffusion method. it has been observed that compounds a-1, a-2, a-3 and a-5 showed excellent activity.(6). insecticidala

8、ctivity agaist armyworm of all the compounds by leaf disc method. it has been observed that all the compounds show no obvious insecticidalactivity. (7). antitumor activity against 3ll, mcf-7, bgc-823, qgy-7701 of compounds a-1a-12 were assayed by the mtt method. it has been observed that compounds a

9、-3, a-5 and a-12 show excellent activity.【關(guān)鍵詞】pictetspengler反應(yīng) -咔啉類生物堿 抑菌 抗腫瘤【英文關(guān)鍵詞】pictetspengler -carboline anti-bacterial activity antitumor activity【目錄】-咔啉類生物堿的合成及其生物活性摘要5-7abstract7-8第一章 文獻綜述11-361.1 咔啉類生物堿11-121.2 咔啉生物堿的提取12-181.2.1 從植物中提取12-151.2.2 從海洋生物中提取15-171.2.3 從其他生物中提取17-181.3 咔啉生物堿的活性

10、18-261.3.1 抗腫瘤活性18-211.3.2 抗骨質(zhì)疏松作用211.3.3 殺蟲活性211.3.4 抗病毒活性21-231.3.5 抗氧化活性231.3.6 抑菌活性23-251.3.7 殺寄生蟲活性251.3.8 與dna 結(jié)合的能力251.3.9 抗抑郁（抑制單胺氧化酶活性等）25-261.4 咔啉類生物堿及其衍生物的化學合成26-341.4.1 以構(gòu)建c 環(huán)為基礎(chǔ)的咔啉類生物堿及其衍生物的合成26-311.4.2 以構(gòu)建b 環(huán)為基礎(chǔ)的咔啉類生物堿及其衍生物的合成31-331.4.3 以構(gòu)建a 環(huán)為基礎(chǔ)的咔啉類生物堿及其衍生物的合成33-341.5 本實驗的設(shè)計思路34-351.6 研究方法35-36第二章 實驗部分36-432.1 化學實驗部分36-412.1.1 試驗中所用的儀器以及試劑等362.1.2 試驗方法與步驟36-412.2 生物活性評價部分41-432.2.1 抑菌活性測定部分412.2.1.1 試驗中的主要儀器412.2.1.2 供試細菌412.2.1.3 供試化合物412.2.1.4 抗細菌活性試驗412.2.2 體外抗腫瘤活性測定部分41-422.2.3 殺蟲活性測定部分42-43第三章 實驗結(jié)果與數(shù)據(jù)分析43-543.1 合成化合物及