I. 利用Passerini反應合成多重含硼化合物 II. 合成含螢光發光團之含硼化合物 III. 利用具掌性之含硼起始物來合成具掌性之含硼Ugi化合物

I. Synthesis of Multiple Boron-containing Passerini Analogs II. Synthesis of Boron-containing Compounds with Fluorescent Tag III. Synthesis of Boron-containing Ugi-4CR Analogs using Chiral Building Block

黃詩晴(Shi-Qing Huang)

指導教授 ： 潘伯申

淡江大學/理學院/化學學系碩士班/碩士(2017年)

https://doi.org/10.6846/TKU.2017.00971

摘要

I. 利用Passerini反應合成多重含硼化合物
本研究為了開發出適用於硼中子捕獲治療 (Boron Neutron Capture Therapy, BNCT) 之藥物，因此利用Passerini反應合成出多重含硼酸α-Acyloxyl Amides化合物 (Scheme 1.)。所得的化合物將繼續由實驗室同學進行深入的結構與活性關係之探討。

II. 合成含螢光發光團之含硼化合物
在BNCT的治療過程中，硼-10在細胞中的含量扮演著治療成功與否的決定因素。然而，硼化合物在細胞中之濃度的檢測通常需要昂貴的設備 (ICP-AES Mass) 和繁瑣的樣品預處理 。日本大阪府立大學的Kirihata教授團隊為了解決這樣的難題發展出了一個螢光發光的分子 DAHMI (Scheme 2.) , ，此分子可與硼酸官能基螯合 (Scheme 3.) 而發出螢光，進而方便研究人員偵測硼酸藥物在細胞中的濃度。所以我的研究目的為利用此螢光基團，來偵測我所合成的硼酸衍生物在細胞中的分佈。

III. 利用具掌性之含硼起始物來合成具掌性之含硼Ugi化合物
雖然Ugi多組成反應為一個極具效率的合成方法，然而其最大的缺點在於其產物皆不具光學活性 (racemic)，為了解決這個問題，本研究利用具有光學活性的(1S,2S,3R,5S)-(+)-2,3-Pinanediol與含硼酸之一級氨起始物形成具有光學活性的起始物，進而希望可以誘導Ugi反應也形成具有光學活性的產物(Scheme 4.)，其結果將會於論文中探討。

關鍵字

硼 ； Passerini反應 ； 掌性中心 ； 螢光標籤

並列摘要

1. Synthesis of Multiple Boron-containing Passerini Analogs :
In order to develop a boron carrier agent suitable for Boron Neutron Capture Therapy (BNCT), a series of multiple boron-containing α-acyloxyl amides compounds (Scheme 1.) were synthesized via Passerini reaction. The resulting compounds currently being evaluated by other student in the lab for biological activities.

2. Synthesis of Boron-containing Compounds with Fluorescent Tag :
In the course of BNCT treatment, the overall concentration of boron-10 in the cells plays a decisive factor in the treatment. However, the determination of the concentration of boron compounds in cells usually requires expensive equipment (ICP-AES Mass) and complicated sample pretreatment. Kirihata and co-workers developed a fluorescent luminescent molecule, DAHMI (Scheme 2.), to solve this problem. This molecule can be chelated with boronic acid to form a fluoresce compound (Scheme 3.), and enables researchers to measure the concentration of boron compounds in cells. My purpose is to use this fluorescent feature to detect the distribution of the synthesized boronic acid derivatives in cells.

3. Synthesis of Boron-containing Ugi-4CR Analogs using Chiral Building Block :
Although the Ugi multicomponent reaction is a highly efficient synthetic strategy, the major drawback of this method is that it only generates products that are racemic. In order to solve this issue, I utilize optically pure ligand, (1S,2S,3R,5S)-(+)-2,3-Pinanediol, and boron-containing primary amine, to form a new chiral building block. It is hypothesized that by using this compounds, we would be able to synthesize the chiral Ugi analogs (Scheme 4.). The results are presented in this chapter.

並列關鍵字

Boron ； Passerini ； fluorescent tag ； chiral building block ； multicomponent

參考文獻

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