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    Title: 含硼胜肽化合物之合成(I);利用Ugi反應合成含硼化合物(II);含硼異腈化合物之合成(III)
    Other Titles: Synthesis of boron-containing peptidyl analogs (I);synthesis of boron-containing analogs via ugi reaction (II);synthesis of boron-containing isocyanide (III)
    Authors: 林孟璇;Lin, Meng-Hsuan
    Contributors: 淡江大學化學學系碩士班
    潘伯申;Pan, Po-Shen
    Keywords: ;Ugi反應;多組成;異腈;boron;Ugi reaction;Multicomponent;isocyanide
    Date: 2014
    Issue Date: 2015-05-04 09:48:11 (UTC+8)
    Abstract: 含硼胜肽化合物之合成(Ⅰ):在傳統的藥物開發中,含硼分子顯少被列入考慮。但近來研究發現含硼分子對其所作用之生化目標具有高度選擇性與高度活性等優點,使許多研究單位逐漸積極投入含硼藥物之開發。本研究中我們合成了兩系列含硼胜肽化合物。此類化合物可以以簡單的合成方法製備與純化。同時我們可以藉由溫和的反應條件,使硼酸、硼酯與三氟硼酸三者不同的官能基進行轉換。

    利用Ugi反應合成含硼化合物(Ⅱ):本部分研究計畫利用Ugi多組成反應(Ugi-4CR)於簡單的反應條件下合成硼酸與硼酯之Ugi化合物,藉由微波方式加速其反應時間,此外,僅利用酸鹼萃取法的方式,即可將粗產物純化,藉此可輕易地合成一系列之含硼Ugi化合物,並為含硼之衍生物提供了獨特的純化路徑。

    含硼異腈化合物之合成(Ⅲ):根據文獻報導,目前已知上百種含有異腈官能基(Isocyanide)之天然物。而這些特殊的天然物在抗菌或抗腫瘤上多具顯著的特效。因此,異腈化合物之合成實為一值得深入研究主題。本研究成功藉由Ugi多組成反應合成出含硼之甲醯胺,接著將之脫水轉換為含硼之異腈化合物。
    Synthesis of Boron-containing Peptidyl Analogs (Ⅰ):In this research, we have designed and synthesized two series of boron-containing analogs.These compounds could be easily synthesized and purified via simple synthetic operations. In addition, boronic acid and its corresponding boron functional groups are successfully synthesized with mild conditions.

    Synthesis of Boron-containing Analogs via Ugi Reaction (Ⅱ):In this research, an Ugi four-component reaction (Ugi-4CR) utilizing formylphenylboronic acids or formylphenylboronate esters under mild condition is developed. The described reactions were accelerated by employing microwave irradiation.In addition, the liquid-liquid acid/base extraction protocol for the purification and isolation of all reported final products were also included making this strategy suitable for the preparation of chemical libraries and provided a unique opportunity to access a broad range of boron-containing analogs.

    Synthesis of Boron-containing Isocyanide (Ⅲ):Isocyanide (or isonitrile) is a unique class of functional groups that appears in many biological active natural products. Many of these isocyanide-based natural products can be used as anti-bacterial or anti-tumor agents. It is thus a valuable target functional group in medicinal chemistry.In this research, I have successfully synthesized 4 boron-containing formamides by microwave assisted Ugi-4CR and have good yields. At the same time, I have successfully converted 2 boron-containing formamides to boron-containing isocyanides.
    Appears in Collections:[化學學系暨研究所] 學位論文

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