中國醫藥大學機構典藏 China Medical University Repository, Taiwan:Item 310903500/41453
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    Title: 固醇類藥物合成新方法開發暨生物活性之探討
    Investigation of New Synthesis Methodology for Steroid Derivatives and Bioactivity Evaluation
    Authors: 曾文哲
    Contributors: 藥物化學研究所碩士班
    Keywords: 固醇類;乙炔化 Steroid;ethynylation
    Date: 2011-07-05
    Issue Date: 2011-10-17 16:58:28 (UTC+8)
    Publisher: 中國醫藥大學
    Abstract: 本論文主要是改善傳統合成α-C17-ethynyl-containing steroid衍生物(例如 mestranol及levonorgestrel),因為使用乙炔氣體,可能產生爆炸性的危害。我們成功發展以一鍋化方式進行ethynylation,並開發出催化性的 desilylation reaction,可更簡便合成出ethynyl-containing steroid化合物(例如mestranol和levonorgestrel)。本研究過程,我們先將類固醇的C-17的位置,順利銜接上α-C17-trimethylsilylacetylenyl,在同一鍋反應中再加入0.05催化量的Tetrabutylammonium fluoride (TBAF),可成功引入α-C17-ethynyl group。
    另一方面延續本實驗室C21-substituted steroid化合物研究,我們實驗室成功發展出以hexamethylenetetramine 試劑將C21-bromo-3α-hydroxyl-
    3β-methoxymethyl-5α-pregnan-20-one轉換成C21-amino-3α-hydroxyl-
    3β-methoxymethyl-5α-pregnan-20-one。
    A one-pot ethynylation and catalytic desilylation reaction was developed for the synthesis of α-C17-ethynyl-containing steroid derivatives (e.g. mestranol and levonorgestrel). Addition of trimethylsilylacetylide to the carbonyl group at C-17 of the steroids yielded the C-17α- trimethylsilylacetylenyl adducts, which was desilylated with a catalytic amount of TBAF (0.050 equiv) in one-pot.

    On the other hand, our laboratory were successfully developed the new amination methodology to convert C21-bromo-3α-hydroxyl- 3β-methoxymethyl-5α-pregnan-20-one to C21-amino-3α-hydroxyl- 3β-methoxymethyl-5α-pregnan-20-one steroidal derivatives. The C21-amino- 3α-hydroxyl-3β-methoxymethyl-5α-pregnan-20-one can be used as the precursor for synthesis of C21- substituted steroid derivatives.
    Appears in Collections:[Graduate Institute of Pharmaceutical Chemistry] Theses & dissertations

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