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研究生:楊凭勲
研究生(外文):Ping-Syun Yang
論文名稱:第一部份:合理設計與合成具抗癌活性之四氫異喹啉與吲哚-喹唑酮共軛結構;第二部份:利用高價碘試劑氧化偶合反應建立3-羥基吡啶類似物之合成與發展
論文名稱(外文):Part I: Rational Design and Synthesis of Tetrahydroisoquinoline- and Indole-Quinazolinone Conjugate with Anticancer Activities;Part II: Synthesis and Development of meta-Hydroxypyridines with Hypervalent Iodine (III) mediated Oxidative Coupling Reaction
指導教授:王志偉王志偉引用關係
指導教授(外文):Chi-Wi Ong
學位類別:博士
校院名稱:國立中山大學
系所名稱:化學系研究所
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:2015
畢業學年度:103
語文別:中文
論文頁數:143
中文關鍵詞:抗癌活性吳茱萸鹼四氫異喹啉喹唑酮無過渡金屬催化反應高價碘試劑3-羥基吡啶
外文關鍵詞:anticancer activitiesevodiaminequinazolonetetrahydroisoquinolinetransition-metal-free catalytic reactionhypervalent iodine reagent3-hydroxypyridine
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本篇論文將分別提出兩部份的研究工作;第一部份我們設計與合成了一系列將四氫異喹啉及喹唑酮兩個具生物活性分子結合為一之新一代有潛力的抗癌藥物,CWO化合物。CWO系列化合中,0-CWO具有最佳之抗癌活性(IC50=0.26 μM, MDA-MB-231 breast adenocarcinoma cels),並在細胞凋亡實驗中發現具有導致細胞早期與晚期之凋亡結果。此外,我亦合成一系列含異原子芳香環之Evodiamine天然物,藉以增加化合物之溶水性。第二部份我們成功發現3-hydroxypyridine在一溫和、環境友善之高價碘試劑下成功得到homocoupling產物,並將其應用在最新議題之無過渡金屬催化反應。
In this thesis, there are two parts in this dissertation. Part I: we have designed and synthesized a series of new generation of protenial anti-cancer drugs containing two biologically active structure tetrahydroisoquinoline and quinazolone, CWO compounds. CWO series of compounds, especially in 0-CWO, which has the best of the anti-cancer activity for IC50 (0.26 μM in MDA-MB-231 breast adenocarcinoma cells), and was found in apoptosis experiments have the results of early and late apoptotic cells. In addition, I also have synthesized a series of hetero-atom aromatic rings for the nature product, evodiamine, in order to increase water solubility of the compounds. The second part of our successful discovery 3-hydroxypyridine in the presence of hypervalent iodine reagent which is in a mild condition, eco-friendly to give homocoupling products successfully. Finally, we use the bipyridine compounds for the application in the transition-metal-free catalytic reactions.
審定書 i
謝誌 ii
中文摘要: iii
英文摘要 iv
目錄 v
表格 viii
流程 ix
圖 xii

第一部份:合理設計與合成具抗癌活性之四氫異喹啉與吲哚-喹唑酮共軛結構 1
第一章 四氫異喹啉生物鹼-RENIERAMYCINS之文獻回顧 1
1.0前言 1
1.1 N-ACYLIMINIUM ION反應 2
1.1.1 胺烷基化與醯胺烷基化反應之比較(Aminoalkylation versus amidoalkylation) 2
1.1.2 N-Amidoiminium在天然物合成之難題 3
1.3 具有四氫異喹啉結構之天然物 6
1.4 RENIERAMYCINS生物活性 9
1.5 四氫異喹啉生物鹼之合成研究 12
1.6 RENIERAMYCINS天然物之合成與介紹 14
1.6.1 Fukuyama的(±)-renieramycin A合成研究 15
1.6.2 Danishefsky的Cribrostatin IV (Renieramycin H)合成研究 16
1.6.3 Magnus的Renieramycin G全合成研究 18
1.6.4 Williams的Renieramycin G全合成研究 20
1.6.5 Williams的Renieramycin H全合成研究 21
1.6.6 Zhu的Renieramycin G全合成研究 22
1.7 結論 23
1.8 參考文獻 24
第二章 設計具有吡嗪基[2,1-B]喹唑啉-3,6-雙酮和四氫異喹啉結構之抗癌藥物 26
2.1 前言: 26
2.2 藥物設計概念-LIGAND FRAGMENT LINK 26
2.3動機 27
2.4 具有喹唑酮(QUINAZOLINONE)結構之化合物 29
2.5 合成策略之逆合成分析 32
2.6合成步驟與結果討論 33
2.7生物活性 39
2.7.1 Sulforhodamine(SRB)腫瘤細胞生長測定法 39
2.8結論 43
2.9 參考資料 44
2.10實驗部份 46
2.11 實驗數據 47
第三章:合成與設計抗癌藥物吳茱萸鹼及增加水溶性 57
3.1摘要: 57
3.2緒論: 57
3.3吳茱萸鹼在藥理學與臨床醫學的潛力 58
3.4化學合成與文獻回顧 60
3.5合成動機 62
3.6吳茱萸鹼(EVODIAMINE)的合成與修飾 63
3.6.1逆合成分析 63
3.6.2 Carboline的合成 64
3.6.3 7-Aza-carboline的合成 65
3.6.4 Isatoic anhydride之合成 66
3.6.5合環反應 67
3.7 生物活性與溶水實驗結果 68
3.8結論 69
3.9參考資料: 70
3.10 實驗數據 72
第二部份:利用高價碘試劑氧化偶合反應建立3-羥基吡啶類似物之合成與發展 76
第四章:文獻回顧-無過渡金屬氧化偶合反應 76
4.1 簡介 76
4.2 第一個反應途徑:自由基途徑(RADICAL PATHWAY): 78
4.3 第二個反應途徑: 自由基陽離子反應(RADICAL CATION PATHWAY)之高價碘試劑應用 90
4.3.1 高價碘試劑 90
4.3.2 高價碘試劑進行碳-碳鍵自身偶合反應 91
4.4 結論 102
4.5 參考資料 102
第五章 利用高價碘試劑氧化偶合反應建立3-羥基類似物之合成與發展 108
5.1 前言 108
5.2 動機 109
5.3 合成 110
5.4 實驗數據 120
5.5 參考資料: 129
表格
表格1.1 SAITO團隊對RENIERAMYCIN G之結構與抗癌活性關係 11
表格1.2 CRIBROSTATIN IV (31)對抗多種癌細胞活性測試 12
表格2.1 PICTET-SPENGLER環化反應 34
表格 2.2 AZA-WITTIG CYCLIZATION OF 36
表格2.3 CWO化合物之細胞毒性 40
表格2.4 確認活性中心癌細胞活性測試 41
表格3.1 EVODIAMINE的擴散效應(THE ANTIPROLIFERATIVE EFFECTS) 59
表格4.1 PHENYLATION OF PYRAZINE 79
表格4.2 KOTBU促使雜原子芳香環與ARYL IODIDES偶合反應 80
表格4.3 COBALT催化及意外發現非過渡金屬催化反應 81
表格4.4 不同的催化劑進行催化反應產率 83
表格4.5 KWONG和LEI利用自由基補捉劑中止反應實驗 84
表格4.6 SHIRAKAWA和HAYASHI團隊發表之非質子型催化偶合反應 85
表格4.7 MOF催化進行不同芳香環ARYLATION 89
表格4.8 PIFA促使分子間偶合反應 92
表格4.9 PREFERENTIAL H−T DIMER FORMATION OF 3- ALKYLTHIOPHENES 94
表格4.10 多電子雜原子芳香環與不同親核性芳香環進行氧化偶合反應 97
表格4.11 雜環化合物與IODONIUM BROMIDE鹽類在IPSO位進行取代反應 99
表格5.1 合成BIPYRIDINE優化條件 112
表格5.3 氮與氧之反應機構調查 116
表格5.4 BIPYRIDINE催化反應 119
流程
流程1.1 胺烷基化與醯胺烷基化 2
流程1.2 KUBO的(±)-SAFRAMYCIN B全合成研究 4
流程1.3 FUKUYAMA的(±)-SAFRAMYCIN B全合成研究 5
流程1.4 FUKUYAMA的(±)-SAFRAMYCIN A全合成研究 5
流程1.5 一般合成四氫異喹啉化合物之關鍵步驟 12
流程 1.6 PICTET-SPENGLER對於四氫異喹啉生物鹼的合成分析 13
流程 1.7 FUKUYAMA的(±)-RENIERAMYCIN A合成研究 16
流程 1.8 DANISHEFSKY的CRIBROSTATIN IV全合成研究 17
流程1.9 MAGNUS的RENIERAMYCIN G全合成研究 19
流程1.10 WILLIAMS的(-)-RENIERAMYCIN H全合成研究 21
流程1.11 ZHU的(-)-RENIERAMYCIN H全合成研究 22
流程2.1 本實驗開發之PICTECT-SPENGLER反應 26
流程2.2 設計新型具生物活性複合化合物 28
流程2.3 具生物活性之喹唑酮化合物 31
流程2.4逆合成分析 32
流程2.5 三環化合物合成 33
流程2.6 合成三重氮醯氯化合物 35
流程2.7 AZA-WITTIG 反應機構 37
流程2.8 比較天然物RENIERAMYCIN H與合成設計 38
流程2.9 合成僅具QUINAZOLINONE結構之化合物與新的合成途徑設計 39
流程3.1吳茱萸鹼(EVODIAMINE) 1之逆合成分析 62
流程3.2 逆合成分析法 63
流程3.3 合成CARBOLINE化合物 64
流程3.4 7-AZA-CARBOLINE 65
流程3.5合成ISATOIC ANHYDRIDE化合物 66
流程3.6合成EVODIAMINE ANALOGUES 67
流程4.1 非過渡金屬催化反應之典型六種反應途徑 77
流程4.2 HOMOLYTIC AROMATIC SUBSTITUTION (HAS)反應 78
流程4.3 HAYASHI團隊提出之可能催化偶合反應途徑 85
流程4.4 YONG團隊發表ZWITTERIONIC RADICAL促使催化偶合反應 86
流程4.5 穩定之ZWITTERIONIC RADICAL經由HAS途徑之可能反應機構 87
流程4.6 MOF促使非勻相催化反應 88
流程4.7 一般三價碘試劑進行氧化偶合反應過程 92
流程4.8 ALKYLTHIOPHENES在PIFA下進行氧化偶合反應 93
流程4.9 3,4-DISUBSTITUTED PYRROLES在PIFA下直接氧化偶合反應 95
流程4.10 氮上具取代基之Α,Β’-BIPYRROLE合成方法 96
流程4.11 HTIB與多電子芳香環反應 96
流程4.12 3號位取代之THIOPHENES在KOSER試劑下反應 98
流程4.13 IODONIUM(III) BROMIDE鹽類扮演重要的氧化偶合中間產物 98
流程4.14 IPSO位置之取代反應性不佳 98
流程4.15 經由CHARGE TRANSFER複合物進行SET偶合反應 100
流程4.16 高價碘鹽類下進行DIARYL ETHER合成 101
流程4.17高價碘鹽類下進行INDOLE環之ARYLATION反應 101
流程4.18高價碘鹽類下進行PYRROLE環之ARYLATION反應 102
流程 5.1 酚類化合物進行去芳香化反應 108
流程5.2 根據文獻之合成動機 109
流程5.3 我們提出的合成重要中間體概念 109
流程5.4 試圖合成關鍵中間體途徑 111
流程5.5 假設之兩種可能反應機制 114
流程5.6 BIPYRIDINE具有位向選擇最可能之反應機構 117
流程5.7 HOMOCOUPLING與CROSSCOUPLING之競爭反應 117
流程5.8 2號位取代與高價碘反應 118

圖1.1 N-ACYLIMINIUM ION反應之代表生物鹼 2
圖1.2 PICTET-SPENGLER反應應用在天然物合成文獻 3
圖1.3 MONO-TETRAHYDROISOQUINOLINE ALKALOIDS 7
圖1.4 BIS- AND TRIS-TETRAHYDROISOQUINOLINE ALKALOIDS 8
圖1.5 THE RENIERAMYCINS 9
圖1.6 RENIERAMYCINS結構 15
圖1.7 RENIERAMYCIN H (CRIBROSTATIN IV)結構 16
圖2.1 本實驗室合成之直線型化合物 26
圖 2.2具喹唑酮骨架之生物鹼 30
圖 2.3具喹唑酮骨架之生物鹼II 31
圖2.4 化合物128引起MDA-MB-231乳癌細胞凋亡 42
圖3.1具QUINAZOLINOCARBOLINE結構之生物鹼 58
圖3.2文獻回顧吳茱萸次鹼 (RUTAECARPINE 2)之逆合成分析 61
圖3.3 EVODIAMINE之官能基修飾 63
圖3.4 EVODIAMINE類似物之生物活性與溶水性實驗 68
圖4.1 SHI提出可能之作用中間體以進行催化偶合反應 82
圖 4.2 常見的三價及五價碘試劑 90
圖5.1 (A)半小時及(B)一小時後反應進行中之LC-MS光譜 115
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