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    Please use this identifier to cite or link to this item: http://ir.lib.ncu.edu.tw/handle/987654321/71383

    Title: 潛力抗癌試劑巴比妥酸共軛衍生物之合成暨開發新穎鋯金屬有機骨架材料水相製備法
    Authors: 郭紜維;Kuo,Yun-Wei
    Contributors: 化學學系
    Keywords: 巴比妥酸;肝纖維化;;金屬有機骨架材料;水相製備
    Date: 2016-08-26
    Issue Date: 2016-10-13 12:47:58 (UTC+8)
    Publisher: 國立中央大學
    Abstract: Part I 潛力抗癌試劑巴比妥酸共軛衍生物之合成
    Part II 開發新穎鋯金屬有機骨架材料水相製備法
      金屬有機骨架材料(MOFs),為一新型態之孔洞材料,其優異的孔洞性及高比表面積的優勢,使得MOFs在多方應用中皆有十分突出的表現,再加上MOFs具有相當良好的化熱穩定性,近期開始被大量研究及使用於石化工業上;同時,隨著環保意識的抬頭及工業成本上的考量,過去用來製備MOFs的溶劑熱合成法,也開始探討水相合成的可能性。在本實驗室過去的研究成果中,成功的在水相中製備出類沸石咪唑骨架材料-90(ZIF-90),同時使用ZIF-90包覆酵素並仍保有酵素活性,但由於ZIF-90的孔隙大小僅3.5 Å,較大的基質無法通過,因此我們極力尋求一個孔徑略大的酵素催化平台。
      UiO-66,孔隙大小6.0 Å之金屬有機骨架材料,同時是目前MOFs結構熱穩定表現最優異之材料,根據軟硬酸鹼理論,高親電子性之鋯金屬易與羧酸基形成高強度鍵結,然而太強的鍵結使得材料無法有效形成結晶,故UiO-66多半在有機溶劑下合成。在實驗室過去的研究中,發現UiO-66的有機配體—對苯二甲酸中若苯環上具有推拉電子基,此推拉電子效應能影響鄰近羧酸官能基之電子密度,進而調控羧酸基與鋯金屬之間的鍵結強弱,促使較低鍵強之鍵結得以得到良好的結晶平衡,且藉由此結晶平衡,我們成功地發現了四氟對苯二甲酸在醋酸水相中有最適當的鍵結力,能在15分鐘內製備出UiO-66-F4。
    ;Part I Design and Synthesis of Barbiturate-Conjugated Derivatives as Potential Anti-Cancer Agents
    Through high-throughput screening (HTS), extensively optimized drug discovery can be carried out these days. Aromatic and non-aromatic heterocyclic rings usually play key roles in interacting with the target biological macromolecules such as the active sites of enzymes. Based on the observations published, these heterocyclic rings can be a quick identification of “hits” to evaluate which heterocyclic derivatives can be the most potential structures in drug discovery.
    With our investigation in this research, we have found that a series of barbiturate derivatives have quite potential bioactivities as pharmacophore. Besides, some published reports have mentioned the synthesized cinnamaldehydes or piperonals derivatives have great potential as anti-cancer or antibacterial agents. Herein, we have synthesized the conjugates of 3,4-methylenedioxycinnamaldehyde and barbiturate. By combining the bioactive aldehydes to barbiturates, the conjugates formed may have a more noticeable activity.
    In this research, we have successfully synthesized a series of modified barbiturates by Knoevenagel condensation with 3,4-methylenedioxy- cinnamaldehyde and barbiturates. And we also synthesize the products with simpler aldehyde structure like benzaldehyde and cinnamaldehyde to discuss the differences. The bio-evaluation of these derivatives was also held to check their activities as anti-hepatoma and anti-fibrosis agent.
    Part II Develop New Water-Based Synthesis of Zirconium-
    Organic Framework
    Metal-Organic Frameworks (MOFs) have numerous applications due to their good chemical/thermal stability, extraordinary porosity and high specific surface area. However, the synthetic methodologies for MOFs are limited in organic solvent system that may damage the environment. As a consequence, developing an environmental friendly approach for synthesizing MOFs is in urgent need. More specifically, inventing a method with water, an absolutely clean resource, as solvent to obtain MOFs is of great value, not to mention the possible huge impact water may have on the reaction. In our previous report, we successfully obtained ZIF-90 under water-based system. Besides, we demonstrated a de novo approach to acquire an enzyme@ZIF-90 composite with substrate selectivity and shielding capability. Nevertheless, the small aperture size of 3.5 Å in ZIF-90 restricted its catalysis ability--that is, the small size of window shields other oversized substrates as well as denaturants. Therefore, to solve the above problem, obtaining other MOFs with bigger size in aperture with water-based approach is what we are trying to do in this thesis.
    UiO-66 with aperture size of 6.0 Å is the most thermal stable structure for MOFs. Our previous research revealed that different functional groups on benzene-1,4-dicarboxylic acid (BDC) could manipulate the bonding strength between Zr and carboxylate groups. Therefore, based on our previous results, we intend to optimize the synthetic condition of UiO-66 under water. Herein, we report the improved condition in which tetrafluoroterephthalic acid acted as organic linkers, and successfully synthesized UiO-66-F4 in minutes under acid aqueous solution.
    Appears in Collections:[Graduate Institute of Chemistry] Electronic Thesis & Dissertation

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