研究生: |
蔡逸蘋 |
---|---|
論文名稱: |
(25R)-3α-胺基-5-螺甾稀之首次合成及規劃其三胺衍生物之合成方法 First Synthesis of Antillidine and Development of a Strategy For Its Triamine Derivatives |
指導教授: | 胡紀如 |
口試委員: | |
學位類別: |
碩士 Master |
系所名稱: |
理學院 - 化學系 Department of Chemistry |
論文出版年: | 2005 |
畢業學年度: | 93 |
語文別: | 英文 |
中文關鍵詞: | steroids 、diosgenin 、antillidine |
相關次數: | 點閱:1 下載:0 |
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Antillidine ((25R)-3-amino-5-spirostene) 為一具有螺甾骨架的胺基類固醇化合物,1992年古巴的科學家Coll報導該化合物可從茄類植物Solanum Antillarum中單離出。在本篇論文中,我們報導antillidine之新合成方法,其為利用皂甘素 (diosgenin) 作為起始物,引用Mitsunobu reaction,經由兩個步驟,成功地合成antillidine,總產率為70%。
Antillidine 與天然物鯊胺 (squalamine) 在類固醇骨架第三號碳上皆具有ㄧ個胺基。鯊胺於1993年被報導其可由狗鯊 (dogfish shark Squalus acanthias) 的肝臟中取得。近年研究發現,鯊胺擁有抑制腫瘤增生及抗癌之活性,因此鯊胺引起了廣泛的研究與合成。
本篇論文中,我們討論一策略,其可合成出鯊胺衍生物,此策略為藉由Antillidine 與所合成出之不同的胺基側鏈進行偶合反應後,可得類似於鯊胺之三胺衍生物。
Antillidine (9), a natural product isolated from Solanum antillarum by Coll et al. in 1992, was synthesized successfully in two steps in 70% overall yields from nature diosgenin. Similar to antillidine (9) is that squalamine also has an amino group attached to the steroid nucleus. On the other hand, squalamine is an aminosterol, which was isolated from tissues of dogfish shark Squalus acanthias by Moore et al. in 1993. Squalamine has gained great attention from scientists because of its antiangiogenic and antitumor activities. The compound possesses an amino side chain at the C-3 position. We planned to develop a strategy for the synthesis of squalamine derivatives by linking antillidine (9) with different amino side chains; meanwhile the products possessed a spiro structure at the C-16 and the C-17 positions of steroid. Six different lengths of side chains containing two nitrogen atoms were also synthesized in good yields (55–65%).
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