碳酸銫介導正交性一鍋化合成 嘧啶衍生物用以建構新的功能化金屬配體;A Cs2CO3-Mediated Orthogonal One-Pot Synthesis of Pyrimidine Derivatives Access to New Functionalized Metal Ligands

Please use this identifier to cite or link to this item: http://ir.lib.ncu.edu.tw/handle/987654321/92080

Title:	碳酸銫介導正交性一鍋化合成嘧啶衍生物用以建構新的功能化金屬配體;A Cs2CO3-Mediated Orthogonal One-Pot Synthesis of Pyrimidine Derivatives Access to New Functionalized Metal Ligands
Authors:	游雅筑;Yu, Ya-Chu
Contributors:	化學學系
Keywords:	嘧啶;細胞胞器靶向探針;傳感器
Date:	2023-08-16
Issue Date:	2024-09-19 14:49:16 (UTC+8)
Publisher:	國立中央大學
Abstract:	嘧啶(pyrimidine)化合物由於它的生物活性及藥物臨床上的應用得到了許多關注，像是天然物維生素 B1、藥物司他夫定(stavudine)等都包含了嘧啶的結構，因此化學家致力於合成嘧啶的衍生物，過去所開發的方法大多需要金屬催化劑、嚴苛的反應條件及繁複的實驗步驟。為了克服這些問題，我們實驗室開發的碳酸銫介導正交性一鍋化合成嘧啶衍生物的方法，可以經由簡單、快速的在溫和反應條件下，從 5-溴-1,2,3-三嗪獲得 2-吡啶基嘧啶及 2-苯基嘧啶等具有獨特金屬螯合位的配體化合物，此類嘧啶配體過去用在金屬錯合物的並不多。在本論文中，我們利用上述簡單碳酸銫介導的方法，合成出具有功能化的苯基嘧啶及吡啶基嘧啶衍生物分別作為銥及釕金屬的配體，並透過疊氮-炔烴環加成反應合成針對細胞核、粒線體、及溶酶體等胞器靶向的金屬錯合物，作為細胞內胞器螢光成像探針；另一方面，我們同時合成含硫醚基的金屬錯合物作為化學傳感器，希望用於細胞中作為偵測次氯酸螢光探針，藉由氧化硫醚基誘導發光的機制來分析細胞內次氯酸濃度。整體而言，我們利用 5-溴基 1,2,3-三嗪作為起始物，利用簡單碳酸銫介導的方法，合成的嘧啶化合物作為配體的策略可為金屬錯合物的合成應用提供廣泛的發展潛力。;Pyrimidine compounds have received widespread attention because of their biological activity and medical applications. Many natural products and drugs contain the pyrimidine in their core structures, such as vitamin B1 and stavudine. Although chemists are dedicated to developing methods for synthesis of the pyrimidines, the problems encountered are the need for metal catalyst, harsh reaction conditions and complicated experiment steps. To overcome these issues, we developed a cesium carbonate-mediated method for the orthogonal one-pot synthesis of pyrimidine derivatives. Using this simple and fast approach under mild reaction conditions, we can prepare the phenylpyrimidines and pyridylpyrimidines as ligands with unique chelation sites in metal complexes. Such pyrimidine compounds have been rarely used as ligands in metalcomplexes in the past. In this thesis, we have synthesized functionalized phenylpyrimidines and pyridylpyrimidines as ligands for iridium and ruthenium metals using this cesium carbonate mediated approach. In addition, we generated the nucleus, mitochondria and lysosome-targeted metal complexes as the bioimaging agents by using the azide-alkyne cycloaddition reactions. On the other hand, we also synthesized the thiolether-bearing metal complexes that can be used as chemosensors for HClO in cells. The qualitative analysis of the analyte can be carried out through the luminescence change of the metal complex. The success of the pyrimidine compound synthesized by our method as a metal ligand provides the potential for the application of metal complexes.
Appears in Collections:	[Graduate Institute of Chemistry] Electronic Thesis & Dissertation

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