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研究生:黃志銘
論文名稱:(I)PolygalatenosidesA,B及其衍生物之合成與活性研究;(II)類茴香黴素小分子之設計、合成與活性研究
論文名稱(外文):(I) Synthesis and Bioevaluation of Polygalatenosides A , B and Derivatives; (II) Design, Synthesis and Bioevaluation of Anisomycin-Based Small Molecules
指導教授:劉瑞雄鄭偉杰
學位類別:博士
校院名稱:國立清華大學
系所名稱:化學系
學門:自然科學學門
學類:化學學類
論文種類:學術論文
論文出版年:2009
畢業學年度:98
語文別:英文
論文頁數:353
中文關鍵詞:茴香黴素呲咯烷酮吡咯烷青黴素
外文關鍵詞:anisomycinpyrrolidinonepyrrolidinebeta lactam
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Abstract
In this thesis, a convergent and straightforward synthetic route for preparation of polygalatenosides A, B, and a series of their derivatives was developed. I also explored the norepinephrine transporter (NET) and serotonin transporter (SERT) inhibition of polygalatenoside derivatives. In the meantime, the anisomycin-like derivatives were also synthesized and examined for inhibition of Saccharomyces cereuisiae, Candida albicans, and human breast cancer cell (MCF7).
In part 1 of this thesis, a small compound library of new polygalatenoside derivatives were synthesized. The first total synthesis of polygalatenosides A and B was performed, and absolute D-configuration of galactoside moeity in A and B was also confirmed for the first time. The biological analysis showed that 3a and 5b did not show the significant inhibition of SERT.
In part 2, seven new anisomycin-like derivatives were synthesized. Our successful synthetic strategy ultilized the structural transformation from amino acid through β-lactam and pyrrolidinone to the amino pyrrolidines. The biological analysis showed the 87d and 87g have little inhibition of MCF7.
中文摘要
於本篇論文中,本人發展一個集中與直接的路徑來製備polygalatenosides
A 與B 及其一系列的衍生物。另外,本人亦探討polygalatenoside 衍生物對於正
腎上腺素及血清素輸送者的抑制效果。同樣地,本人也合成了類茴香黴素的衍生
物並且測試其對啤酒酵母、白色念珠菌與人類乳癌細胞之抑制。
在本論文的第一部分,本人合成新polygalatenoside衍生物的小型化合物資料
庫。對於polygalatenosides A與B來說,我們不但完成了首次的全合成,而且在其
半乳糖的結構部分也證實為D組態。在生物活性分析的數據顯示出,化合物3a與
5b對血清素輸送者具有小規模的抑制效果。
在第二部分中,本人合成了七個類茴香黴素的衍生物。在我們的成功合成策
略裡,利用了幾種結構之間的轉換,包括胺基酸、β-內醯胺、呲咯烷酮與胺基吡
咯烷等。 在生物活性分析的數據顯示出,化合物87d與87g對人類乳癌細胞具有
小規模的抑制效果。
Contents
English Abstract ............................................................................................................i
Chinese Abstract ...........................................................................................................ii
Acknowledgement……………………………………………………………….......iii
Abbreviations……………………………………………………………………….iv
Contents ........................................................................................................................vi
Part 1: Synthesis and bioevaluation of polygalatenosides A , B and derivatives…….1
Abstract ........................................................................................................................2
Introduction……………………………………………………………………………3
Results…………………………………………………………………………………7
Discsussion…………………………………………………………………………...24
Conclusion……………………………………………………………………………30
Experimental Section………………………………………………………………...31
References……………………………………………………………………………64
Part 2: Design, synthesis and bioevaluation of anisomycin-based small molecules...69
Abstract………………………………………………………………………………70
Introduction…………………………………………………………………………..71
Results………………………………………………………………………………..75
Discussion……………………………………………………………………………86
Conclusions………………………………………………………………………….91
Experimental Section………………………………………………………………..92
References…………………………………………………………………………..115
Spectra .......................................................................................................................119
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