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    Please use this identifier to cite or link to this item: https://tkuir.lib.tku.edu.tw/dspace/handle/987654321/102749

    Title: 銅催化氨化反應合成新穎的氨基類黃酮分子作為有效的抗氧化劑以及其他抗氧化分子結構的修飾作為藥物用途
    Authors: 施增廉
    Contributors: 淡江大學化學學系
    Keywords: 抗氧化劑;黃酮類;自由基;氨基黃酮類分子;汞離子的偵測器;抗發炎;抗癌藥物;aminoflavones;antioxidant;chelating agents;flavones;flavonoids;radical inhibitors
    Date: 2013-08
    Issue Date: 2015-05-04 14:25:01 (UTC+8)
    Abstract: 存在於天然物中的黃酮類或類黃酮分子已超過6500種,除了當成保健藥品使用外,其廣泛的生 物活性的特性也用於作為藥物,因此它們的分離及合成也經常被報導。這類分子主要為A、B、C環 組成,而環上具有一些官能基,主要為氫氧基(-OH),其角色為當成金屬的螯合劑或自由基的捕獲劑, 因此可以防止體内產生過多的自由基,進一步保護身體。目前為止的合成,大部分是合成具氫氧基的 類黃酮分子,而具相同角色的氨基類黃酮被報導的次數卻不多,主要因為是他們多屬非天然的。101 年度我們提出這類具氨基類黃酮分子的合成,我們也順利合成數個分子,後並用於斑馬魚的測試及發 表於期刊,除此之外,其中一個分子在人類乳癌細胞(Her2)的測試上,具有優於一般類黃酮的生物活 性,這更激起我們對這方面分子合成的研究,主要也是因為這方面分子被合成的並不多,因此可發展 的空間還很大。 A、B環上具鹵素官能基的苯環分子多可買到或方便合成,利用已知反應構成黃酮類的架構,其 合成方法也成熟且產率高,由於環上已具有鹵素原子,因此我們可利用一些氨化方式將它置換成氮。 我們發表在2012年Molecules期刊的氨基黃酮類分子合成,是利用已有的氨基苯環分子,這類合成 優點是不需氫化或去保護基的步驟;但缺點在第一步的偶合產率,因溶劑及另一起始物而差異性非常 大。因此,本年度合成方式將改善,較我們發表在Molecules好處在於,並非所有具氨基的苯環分子 都可買到。於是將氨化反應放在合成的最後一步,因此第一步偶合產率也不會受限,比較有可能克服 產率低的問題,或是可增加多元性。 一般氨化反應是將苯環上具有的-NO2、N3氫化後或醯胺基去保護獲得,近年報導氨化的方法將 被利用於這類分子的合成,而催化劑的使用多為Cu,因此我們想嘗試不同的Cu催化劑及氨化藥品; 除此之外,將鹵素置換成-CF3,因為含氟原子在分子上可改變生物活性。 除了將氨的黃酮類分子在結構上做得更深入,也會結合系上理論計算的同仁在做結構最佳化 (QUSAR)外,我們同時也注意到關於抗氧化咖哩成分中的分子,針對其結構上的修飾並結合硼的試 劑可做為染料或光學材料;除此之外,將咖哩分子修飾成含硫分子,可做為汞、氰胺離子的偵測器。 未來我們將把這些分子作更廣泛的生物活性測試,冀望能在這些分子的合成方面能找到適合的抗 發炎、抗氧化物、或抗癌藥物。
    There are more than 6500 flavonids were found in nature up to date. They are used not only as health care agents but also as drugs due to their biological properties. Therefore, their isolations and syntheses are widely reported. Flavonoids are composed of many hydroxyl groups. This functional group is served as chelating agents of metals as well as radical inhibitors (antioxidants). On the other hand, the amino moiety plays the same role as hydroxyl group. However, their syntheses and biological activities were barely reported. We have published the synthesis of aminoflavones and their biological activities on zebrafish larvae. We also found that these agents possessed more potent against tumor cells (Her2) superior to certain drugs. These promising results prompt us to investigate more on their potentials. The synthetic methods of flavonoids are well-established and their starting materials are most commercially available. Since either A or B rings are contained halide groups, they can be easily replaced by amino group via amination. We have published a facile synthesis of aminoflavones in three steps than the reported method in 2012. In this report, our advantage was to apply the readily available starting material with amino groups. However, the yields were variable owing to the existing functional groups on the arenes. This problem can be overcome if the amino group was introduced at the last stage. The existing method for amination was obtained from the reduction of nitro, azide, or deamidation。We will employ the copper catalyzed the amination. Besides, we will introduce the trifluoromethane into flavones to enhance their biological activities. It is worthy to investigate in more detail in the syntheses of aminoflavones. We will collaborate with theoretical chemists on QUSAR method to predict the optimization of molecules. We also extend our scopes on the syntheses of other antioxidants, such as curcumin, and their applications on optical materials and detectors. We will investigate the biological activities of aminoflavones and wish to obtain the candidates of lead compounds in the future.
    Appears in Collections:[Graduate Institute & Department of English] Research Paper

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