第一部分: 聯芳基團 (Biaryl) 是許多具生物活性及藥物分子的一個重要子結構，也因此超過一世紀的合成化學家尋求創新及更高效能的芳香基團間鍵的形成。由於利用過渡金屬的限制在於合成藥物時須先排除金屬不純物的殘留，及金屬催化劑的成本，因此本實驗目的在於找到有機催化劑來活化碳氫鍵進行芳香環的耦合反應，分別利用實驗室合成的液晶鄰二氮雜菲當有機催化劑，進行不同的芳香環及雜環耦合化合物。
第二部分: 設計小分子來誘導或穩定G-四股DNA結構，可以達到抑制端粒的活性，進而達到抗癌的效果。首先改善過去實驗室合成雙喹啉途徑，縮減步數。除此之外，過去實驗室所合出來雙喹啉寡吡咯醯胺的共軛化合物，由於其結構太過剛硬，雖然會對G-四股DNA有所鍵結，但是穩定G-四股DNA的效果有限。本實驗選用兩種途徑，試圖引入橋接基甘胺酸，使其整體結構變為較柔軟，期望其構形能更吻合G-四股DNA，進而對G-四股DNA鍵結力增強。

Part I: The substructure of biaryl is an important motif in many pharmaceutically relevant and biologically active compounds. As a result, for over a century, organic chemists have sought to develop new and more efficient aryl-aryl bond forming methods. However, using of transition metals to synthetic drugs is limited by residuals of metal impurities and the financial cost of the metal catalyst. Therefore the purpose of our experiment is to find an organocatalytic method for constructing biaryls through aromatic C-H activation. Synthetic phenanthroline derivatives were treated as organocatalyst for different aromatic and heterocyclic ring coupling reactions.
Part II: Inhibition of telomerase activity through inducing or stabilization of G-quadruplex DNA structures of human telomere was capable to achieve the anti-cancer effect. The first improvement is the synthesis of Bis-quinoline in the past laboratory ways to reduce the number of steps. Synthetic Bis-quinoline oligopyrrole compounds were found to interact with G-quadruplex DNA slightly and they were assumed to be limited by the rigid structure. In this study, we are attempting to introduce glycine as the connection bridge between bis-quinoline and oligopyrrole. Therefore the softer structures are expecting to better fit into the G-quadruplex DNA secondary structure.

誌謝……………………………………………………………………………….. II
中文摘要………………………………………………………….………………. III
英文摘要………………………………………..………………………………… IV
目錄……………………………………………..………………………………… V
圖目錄………………………………………..…………………………………… VII
表目錄………………………………………..…………………………………… IX
流程目錄………………………………………..………………………………… X
1 有機催化劑活化碳氫鍵進行芳香基團耦合反應 1
1.1 聯芳基團的介紹 1
1.1.1 過渡金屬耦合反應 1
1.1.2 有機催化耦合反應 6
1.1.2.1 有機催化劑的反應機構 10
1.2 研究動機 13
1.3 結果與結論 14
1.4 結論 20
1.5 實驗儀器及藥品 22
1.6 實驗步驟 24
1.7 參考文獻 27
2 調控雙喹啉寡吡咯醯胺共軛化合物 28
2.1 G-四股DNA結構抑制癌細胞機制 28
2.2 G-四股DNA介紹 30
2.2.1 G-四股DNA結構 30
2.2.2 G-四股DNA結構的變數 (Variations) 32
2.2.3 G-四股DNA結構配體的有機分子 35
2.3 實驗室合成雙喹啉寡吡咯醯胺的共軛化合物 38
2.4 研究動機 42
2.5 結果與討論 45
2.5.1 合成雙喹啉化合物 45
2.5.2 合成寡吡咯醯胺化合物 50
2.5.3 合成雙喹啉寡吡咯醯胺化合物 53
2.6 結論 57
2.7 實驗儀器及藥品 58
2.8 實驗步驟 60
2.9 參考文獻 79

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