系統識別號 | U0002-0907201311160200 |
---|---|
DOI | 10.6846/TKU.2013.00251 |
論文名稱(中文) | 含硼一級胺類化合物之合成及其應用 |
論文名稱(英文) | Synthesis of Boron-containing Primary Amines and Their Applications |
第三語言論文名稱 | |
校院名稱 | 淡江大學 |
系所名稱(中文) | 化學學系碩士班 |
系所名稱(英文) | Department of Chemistry |
外國學位學校名稱 | |
外國學位學院名稱 | |
外國學位研究所名稱 | |
學年度 | 101 |
學期 | 2 |
出版年 | 102 |
研究生(中文) | 鍾勝烜 |
研究生(英文) | Sheng-Hsuan Chung |
學號 | 600180060 |
學位類別 | 碩士 |
語言別 | 繁體中文 |
第二語言別 | |
口試日期 | 2013-06-21 |
論文頁數 | 168頁 |
口試委員 |
指導教授
-
潘伯申
委員 - 黃俊誠 委員 - 魏屹 |
關鍵字(中) |
硼 peptoid 一級胺 Ugi-4CR Suzuki reaction Gabriel reaction |
關鍵字(英) |
boron peptoid primary amine Ugi-4CR Suzuki reaction Gabriel reaction |
第三語言關鍵字 | |
學科別分類 | |
中文摘要 |
本研究成功利用優化之Gabriel reaction合成六個含硼之一級胺類化合物 (Fig. 1)。由於這六個含硼一級胺類化合物皆在溫和的條件下予以合成,因此所得產率皆高於50%以上 (Scheme 1,2)。 以含硼一級胺產物為Ugi多組成反應(Ugi-4CR)之起始物並藉由微波輔助條件,本研究成功合成含硼之peptoid衍生物。而這些含硼之peptoid衍生物可藉由一鍋化水解反應,將其轉變為相對應之硼酸化合物 (Fig. 2)。最後,這些Ugi-4CR之peptoids化合物可藉由Suzuki coupling reaction更進一步修飾以達到將結構複雜化的目的 (Fig. 3)。 |
英文摘要 |
In this study, the modified Gabriel synthetic condition was developed to build six boron-containing primary amines in good to excellent yields (Fig. 1). This modified condition allowed the synthesis to carry out in mild synthetic processes (Scheme 1,2). Further, the desired boron-containing primary amines were further utilized to construct the peptoid analogs via microwave assisted Ugi four component reaction (Ugi-4CR) (Fig. 2). In addition, these Ugi-4CR boronate esters were converted to the corresponding boronic acids by a one-pot hydration reaction. Finally, the peptoid structures can be further modified by incorporating aryl/heteroaryl component via palladium mediated Suzuki coupling reaction (Fig. 3). |
第三語言摘要 | |
論文目次 |
目 錄 謝誌 I 中文摘要 II 英文摘要 IV 目錄 VI 圖表目錄 X 附圖目錄 XVI Chapter 1 緒論 1 1.1 研究動機 1 1.2 研究目的 3 Chapter 2 文獻回顧 5 2.1 Peptide藥物之介紹 5 2.1.1 Peptide藥物之優缺點 5 2.1.2 Peptide藥物之改良 6 2.2 Peptoid藥物之介紹 7 2.2.1 Petoid藥物之特點 7 2.2.2 Peptoid藥物之合成 8 2.3 含硼藥物之介紹 11 2.3.1 硼化學簡介 11 2.3.1.1 硼酸(Boronic acids) 11 2.3.1.2 硼酯(Boronate esters) 13 2.3.1.3 三氟硼酸鹽類化合物(Trifluoroborates) 14 2.3.2 含硼化合物在合成上之應用 14 2.3.2.1 Metal-catalyzed cross-couplings 15 2.3.2.2 Petasis reaction 15 2.3.3含硼化合物在藥物化學上之應用 16 2.3.3.1. 酵素抑制劑 18 2.3.3.2 蛋白酶體抑制劑 27 2.3.3.3 抗癌技術與治療 32 2.3.3.4 現階段之FDA臨床藥物 34 2.4 Multiconpoment Reactions (MCRs)之介紹 36 2.4.1 MCRs之特點 36 2.4.2 Ugi Reaction之應用 41 2.4.3 含硼Ugi Reaction之介紹 46 Chapter 3 結果與討論 48 3.1 含硼一級胺之合成 48 3.1.1 BF3K amine之合成 48 3.1.2 Bpin amine之合成 53 3.1.3 Bpin amine之One-Pot合成 59 3.1.4 Bpin amine salt之合成 63 3.2 含硼一級胺之應用 66 3.2.1 Bpin Ugi之合成 66 3.2.2 B(OH)2 ugi之合成 70 3.2.3 Suzuki Reaction的合成 72 Chapter 4 結論 75 Chapter 5藥品、實驗步驟與儀器 76 5-1 藥品介紹 76 5-2 實驗儀器與測試方法 78 5-3 含硼一級胺實驗步驟 79 5-4 含硼一級胺光譜 90 5-5 含硼Ugi實驗步驟 93 5-6 含硼Ugi光譜 103 5-7 Suzuki實驗步驟 108 5-8 Suzuki光譜 111 5-9 生物活性評估與方法 113 附錄一 參考文獻 115 附錄二 光譜圖 126 圖表目錄 Fig. 1.1一般的peptide與peptoid之構型 2 Fig. 1.2含硼官能基之應用 4 Fig. 2.1各種不同peptidomimetics結構 6 Fig. 2.2硼衍生物之命名 11 Fig. 2.3常見硼酸型態 12 Fig. 2.4常見硼酯型態 13 Fig. 2.5常見硼酸鹽類型態 14 Fig. 2.6中性的三角平面之硼酸與親核試劑進行配位後會變形成陰性的四面體構型 17 Fig. 2.7最早發現的含硼天然物Boromycin 17 Fig. 2.8凝血酶抑制劑 20 Fig. 2.9凝血酶抑制劑 21 Fig. 2.10 fXa抑制劑 21 Fig. 2.11類水蛭素之凝血酶抑制劑 22 Fig. 2.12推測之水合物抑制機制 22 Fig. 2.13 α-chymotrypsin抑制劑 23 Fig. 2.14 β-lactamases抑制劑 24 Fig. 2.15 HCV抑制劑 24 Fig. 2.16 DPPIV抑制劑 25 Fig. 2.17精胺酸脢抑制劑 25 Fig. 2.18一氧化氮合酶含硼抑制劑 26 Fig. 2.19 26S蛋白酶質體 28 Fig. 2.20硼替佐米 32 Fig. 2.21硼中子捕獲治療(BNCT,Boron Neutron Capture Therapy) 33 Fig. 2.22目前應用於各類型硼之中子捕獲治療藥物 34 Fig. 2.23上圖為多步合成反應,下圖為MCRs 37 Fig. 2.24藉由MCR所開發之藥物 40 Fig. 2.25針對Ugi酸基之其他可替換官能基 42 Fig. 2.26針對Ugi胺基之其他可替換官能基 42 Fig. 2.27 Ugi環化反應之設計 43 Fig. 2.28各種不同含硼化合物 47 Fig. 3.1目標之化合物 48 Fig. 3.2推測之化合物 49 Fig. 3.3 BF3K官能基氧化為OH官能基 52 Fig. 3.4目標之化合物 53 Fig. 3.5 (a)氯化物 (b)含methyl methanesulfonate離去基之化合物 55 Fig. 3.6含硼一級胺 58 Fig. 3.7硼酸與硼酯可以藉由酸鹼度加以調控 65 Fig. 3.8進行Ugi-4CR所需起始物 67 Fig. 3.9含Bpin之Ugi-4CR產物 69 Fig. 3.10含B(OH)2之Ugi-4CR產物 71 Fig. 3.11有機鹵化物與Pd催化劑 72 Fig. 3.12 Suzuki cross-coupling之產物 73 Scheme 2.1最起初peptoid的合成 9 Scheme 2.2 peptoid的“submonomer”之固相合成 10 Scheme 2.3硼酸易受到環境pH值的改變而影響構型 12 Scheme 2.4硼酸化合物於cross-coupling之反應 15 Scheme 2.5由Petasis reaction合成出不同官能機化合物 16 Scheme 2.6硼酸化合物在四面體轉換 18 Scheme 2.7硼酸化合物對蛋白酶抑制機制簡圖 19 Scheme 2.8胱胺酸蛋白酶抑制機制 27 Scheme 2.9a Ugi反應基本的四大元素 41 Scheme 2.10 Solid-Phase MCRs of Ugi Reaction 44 Scheme 2.11 GSK藉由Ugi-4CR所合成之DKP類藥物 45 Scheme 2.12 Lemonomycin之Ugi-4CR 46 Scheme 3.1硼官能基轉換 48 Scheme 3.2含BF3K之一級胺合成步驟 51 Scheme 3.3含BF3K之一級胺合成步驟 52 Scheme 3.4 含氟之一級胺合成步驟 58 Scheme 3.5有機鹼與無機鹼在氯化反應中推測之反應機制 61 Scheme 3.6首次使用One-Pot反應合成出含硼一級胺 62 Scheme 3.7用One-Pot反應合成出含硼一級胺鹽 65 Scheme 3.8 Suzuki cross-coupling 72 Table 2.1含硼藥物之臨床試驗 34 Table 2.2大部分常見的MCRs 37 Table 2.3 MCRs的類型 40 Table 3.1含BF3K之一級胺條件測試 49 Table 3.2 B(OH)2轉Bpin官能基 54 Table 3.3 Aldehyde還原為Alcohol官能基 54 Table 3.4 Alcohol轉換為phthalimide基團 56 Table 3.5 phthalimide基團轉換為一級胺 57 Table 3.6 Alcohol轉換為phthalimide基團 59 Table 3.7一級胺轉鹽類 64 Table 3.8利用微波裝置進行Ugi-4CR之優化試驗 66 Table 3.9含硼Ugi-4CR之合成 68 Table 3.10含硼Ugi-4CR之合成 70 Table 3.11 Suzuki cross-coupling之合成 73 附圖目錄 附圖 1化合物3.8a之1H-NMR (300 MHz, CDCl3-d3) 130 附圖 2化合物3.8a之13C-NMR (75.5 MHz, CDCl3-d3) 131 附圖 3化合物3.8a之11B-NMR (192.5 MHz, CD3OD-d4) 131 附圖 4化合物3.8b之1H-NMR (300 MHz, CDCl3-d3) 132 附圖 5化合物3.8b之13C-NMR (75.5 MHz, CDCl3-d3) 132 附圖 6化合物3.8b之11B-NMR (192.5 MHz, CD3OD-d4) 133 附圖 7化合物3.8c之1H-NMR (300 MHz, CDCl3-d3) 133 附圖 8化合物3.8c之13C-NMR (75.5 MHz, CDCl3-d3) 134 附圖 9化合物3.8c之11B-NMR (192.5 MHz, CD3OD-d4) 134 附圖 10化合物3.8d之1H-NMR (300 MHz, CDCl3-d3) 135 附圖 11化合物3.8d之13C-NMR (75.5 MHz, CDCl3-d3) 136 附圖 12化合物3.8d之11B-NMR (192.5 MHz, CD3OD-d4) 136 附圖 13化合物3.8e之1H-NMR (300 MHz, CDCl3-d3) 137 附圖 14化合物3.8e之13C-NMR (75.5 MHz, CDCl3-d3) 137 附圖 15化合物3.8e之11B-NMR (192.5 MHz, CD3OD-d4) 138 附圖 16化合物3.8f之1H-NMR (300 MHz, CDCl3-d3) 138 附圖 17化合物3.8f之13C-NMR (75.5 MHz, CDCl3-d3) 139 附圖 18化合物3.8f之11B-NMR (192.5 MHz, CD3OD-d4) 139 附圖 19化合物3.12a之1H-NMR (300 MHz, CDCl3-d3) 140 附圖 20化合物3.12a之13C-NMR (75.5 MHz, CDCl3-d3) 140 附圖 21化合物3.12a之11B-NMR (192.5 MHz, CDCl3-d3) 141 附圖 22化合物3.12b之1H-NMR (300 MHz, CDCl3-d3) 141 附圖 23化合物3.12b之13C-NMR (75.5 MHz, CDCl3-d3) 142 附圖 24化合物3.12b之11B-NMR (192.5 MHz, CDCl3-d3) 142 附圖 25化合物3.12c之1H-NMR (300 MHz, CDCl3-d3) 143 附圖 26化合物3.12c之13C-NMR (75.5 MHz, CDCl3-d3) 143 附圖 27化合物3.12c之11B-NMR (192.5 MHz, CD3OD-d4) 144 附圖 28化合物3.12e之1H-NMR (300 MHz, CDCl3-d3) 144 附圖 29化合物3.12e之13C-NMR (75.5 MHz, CDCl3-d3) 145 附圖 30化合物3.12e之11B-NMR (192.5 MHz, CD3OD-d4) 145 附圖 31化合物3.12e之HMQC-2D NMR 146 附圖 32化合物3.12e之HMBC-2D NMR 146 附圖 33化合物3.12e之HMBC-2D NMR (expand) 147 附圖 34化合物3.16a之1H-NMR (300 MHz, CDCl3-d3) 148 附圖 35化合物3.16a之13C-NMR (75.5 MHz, CDCl3-d3) 148 附圖 36化合物3.16a之11B-NMR (192.5 MHz, CD3OD-d4) 149 附圖 37化合物3.16b之1H-NMR (300 MHz, CDCl3-d3) 149 附圖 38化合物3.16b之13C-NMR (75.5 MHz, CDCl3-d3) 150 附圖 39化合物3.16b之11B-NMR (192.5 MHz, CD3OD-d4) 150 附圖 40化合物3.16c之1H-NMR (300 MHz, CDCl3-d3) 151 附圖 41化合物3.16c之13C-NMR (75.5 MHz, CDCl3-d3) 151 附圖 42化合物3.16c之11B-NMR (192.5 MHz, CDCl3-d3) 152 附圖 43化合物3.16d之1H-NMR (300 MHz, CDCl3-d3) 152 附圖 44化合物3.16d之13C-NMR (75.4 MHz, CDCl3-d3) 153 附圖 45化合物3.16d之11B-NMR (192.5 MHz, CDCl3-d3) 153 附圖 46化合物3.16e之1H-NMR (300 MHz, CDCl3-d3) 154 附圖 47化合物3.16e之13C-NMR (150.9 MHz, CDCl3-d3) 154 附圖 48化合物3.16e之11B-NMR (192.5 MHz, CDCl3-d3) 155 附圖 49化合物3.17a之1H-NMR (300 MHz, CD3OD-d4) 155 附圖 50化合物3.17a之13C-NMR (75.5 MHz, CD3OD-d4) 156 附圖 51化合物3.17a之11B-NMR (192.5 MHz, CD3OD-d4) 156 附圖 52化合物3.17b之1H-NMR (300 MHz, CD3OD-d4) 157 附圖 53化合物3.17b之13C-NMR (150.9 MHz, CD3OD-d4) 157 附圖 54化合物3.17b之11B-NMR (192.5 MHz, CD3OD-d4) 158 附圖 55化合物3.17c之1H-NMR (300 MHz, CD3OD-d4) 158 附圖 56化合物3.17c之13C-NMR (75.4 MHz, CD3OD-d4) 159 附圖 57化合物3.17c之11B-NMR (192.5 MHz, CD3OD-d4) 159 附圖 58化合物3.17d之1H-NMR (300 MHz, CD3OD-d4) 160 附圖 59化合物3.17d之13C-NMR (75.4 MHz, CD3OD-d4) 160 附圖 60化合物3.17d之11B-NMR (192.5 MHz, CD3OD-d4) 161 附圖 61化合物3.17e之1H-NMR (600 MHz, CD3OD-d4) 161 附圖 62化合物3.17e之13C-NMR (75.4 MHz, CD3OD-d4) 162 附圖 63化合物3.17e之11B-NMR (192.5 MHz, CD3OD-d4) 162 附圖 64化合物3.17e之HMQC - 2D NMR 163 附圖 65化合物3.17e之HMBC - 2D NMR 164 附圖 66化合物3.19a之1H-NMR (300 MHz, CDCl3-d3) 165 附圖 67化合物3.19a之13C-NMR (150.9 MHz, CDCl3-d3) 165 附圖 68化合物3.19b之1H-NMR (300 MHz, CDCl3-d3) 166 附圖 69化合物3.19b之13C-NMR (75.5 MHz, CDCl3-d3) 166 附圖 70化合物3.19c之1H-NMR (600 MHz, CD3OD-d4) 167 附圖 71化合物3.19c之13C-NMR (150.9 MHz, CD3OD-d4) 167 附圖 72化合物3.19d之1H-NMR (600 MHz, CDCl3-d3) 168 附圖 73化合物3.19d之13C-NMR (75.5 MHz, CDCl3-d3) 168 |
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