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    Title: 合成具抗氧化能力的氨黃酮化合物
    Other Titles: Synthesis of aminoflavones as antioxidants
    Authors: 蕭智昂;Hsiao, Chih-Ang
    Contributors: 淡江大學化學學系碩士班
    施增廉;Shih, Tzenge-Lien
    Keywords: 抗氧化劑;貝克-文卡塔拉曼重排反應;氨黃酮;antioxidant;Baker-Venkataraman Rearrangement;Aminoflavone
    Date: 2012
    Issue Date: 2013-04-13 11:04:06 (UTC+8)
    Abstract: 類黃酮 (flavonoids)是一種廣泛存在於自然界中的化合物,分子架構由 C6-C3-C6組成,因它具有良好的生物活性,如:自由基清除劑、金屬離子螯合劑、氧化酶抑制劑甚至可做為抗癌藥物而倍受關注。
    近五十年來,許多科學家致力於合成新穎的類黃酮化合物,藉由修飾官能基,看其是否有更好的生物活性。然而,大部分合成類黃酮上的官能基都以羥基、醣基或鹵素元素為主,氨基的類黃酮則是少之又少。所以我們選擇黃酮類 (flavone)為主結構並以合成氨黃酮 (aminoflavone)為目標,期望它有更好的活性。
    在以往製備氨黃酮的方式,通常是先合成硝基黃酮後再將其還原成氨黃酮。在本論文中,我們則以交換官能基的方式來製備氨黃酮。我們以兩種簡單的苯環結構,經由偶合反應、貝克-文卡塔拉曼重排反應 (Baker-Venkataraman Rearrangement)、酸催化合環反應來製備黃酮化合物的主體結構,再將具有鹵素官能基的黃酮化合物,經由銅粉來促使它氨化,成功的發展出新的氨黃酮的製備方法。
    Flavonoids are widely distributed in our environment. Their main structure were composed as C6-C3-C6. Their bioactivities are, such as ROS-scavenging, metal chelator, oxidase inhibitors, and prevent cancer, and attrack much interests.
    In order to develop better bioactivities, various functional groups have been used for the generation of flavonoid derivatives. The functional group used of flavonoids are mainly hydroxyl, glycosyl groups or halide groups. However, aminoflavonoids were very few. Therefore, we selected flavone as framework to synthesize aminoflavone and evaluate their bioactivties on zebrafish larvae.
    The existing method in preparation of aminoflavones was obtained by the reduction of nitroflavone. In this article, we introduce the amino groups at early stage thus reduce the synthetic steps to compare with the exsiting methods. We applied two commercially available starting materials via coupling reaction, Baker-Venkataraman Rearrangement and acid-catalyzed cyclization to synthesize aminoflavones. We also replaced the halogen with amino group medidated by Cu powder to synthesize the aminoflavone.
    Appears in Collections:[化學學系暨研究所] 學位論文

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