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研究生:戴秀芳
研究生(外文):Hsiu-Fang Tai
論文名稱:3-取代9-芳基甲基咔唑類衍生物之合成與抗癌活性
論文名稱(外文):Synthesis and anticancer activity of 3-substituted 9-arylmethylcarbazole derivatives
指導教授:黃麗嬌黃麗嬌引用關係
學位類別:碩士
校院名稱:中國醫藥大學
系所名稱:藥物化學研究所碩士班
學門:醫藥衛生學門
學類:藥學學類
論文種類:學術論文
論文出版年:2009
畢業學年度:97
語文別:中文
論文頁數:153
中文關鍵詞:唑類衍生物抗癌
外文關鍵詞:carbazole derivativesanticancer
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為延續本實驗室一系列carbazole類衍生物之化學合成及其抗癌活性的探討,著者合成一系列3,6-substituted 9-trimethoxybenzylcarbazole,以及9-trimethoxybenzyl以不同芳基甲基取代的carbazole衍生物,並探討所合成的化合物之抗癌活性。
首先,合成方法以carbazole為起始物,與3,4,5-trimethoxybenzylchloride反應生成9-trimethoxybenzylcarbazole (1),接著將化合物1以POCl3/DMF進行Vielsmeir formylation得化合物1a,將化合物1a以NaBH4進行還原反應得到化合物1d。將化合物1在AlCl3與醋酸酐存在下進行乙醯化反應,得單乙醯化合物1b及雙乙醯化合物1c。
此外,另將carbazole與arylmethyl chloride反應,得到相對應的化合物9-arylmethyl carbazole (2-5),將化合物2-5以POCl3/DMF進行Vielsmeir formylation得化合物2a-5a,接著將化合物2a-5a以NaBH4進行還原反應得到相對應的化合物2d-5d。
將這些合成之化合物進行抗癌活性測試,結果顯示部分化合物具明顯的抗癌活性,其中化合物(9-(3,4,5-trimethoxybenzyl)-9H-carbazol-3-yl)methanol (1d)對血癌細胞HL-60及K562、肝癌細胞Hep3B、乳癌細胞MCF7、卵巢癌細胞2774及SKOV3、肺癌細胞H226、H460之抑制活性IC50皆可達10-7-10-9 M,因此化合物1d相當值得進一步探討其抗癌活性。
In order to continue our investigation of novel anticancer agents and their anticancer activities, we synthesized a series of 3,6-substituted 9-trimethoxy benzylcarbazole and 9-arylmethylcarbazole and evaluated for their anticancer activities.
Initially, reaction of carbazole and 3,4,5-trimethoxybenzylchloride yields 9-trimethoxybenzylcarbazole (1). Subsequently, compound 1 underwent Vielsmeir formylation by treating with POCl3/DMF to give compound 1a. Compound 1a underwent reduction by treating with NaBH4 to give compound 1d, and compound 1 was treated with AlCl3 /acetic anhydride yield monoacetyl product 1b and diacetyl product 1c.
Furthermore, reaction of carbazole and arylmethyl chloride yields corresponding 9-arylmethylcarbazoles (2-5). Compounds 2-5 underwent Vielsmeir formylation by treating with POCl3/DMF to give corresponding compounds 2a-5a. Compounds 2a-5a underwent reduction by treating with NaBH4 to give corresponding compounds 2d-5d.
These synthesized compounds were evaluated for their cytotoxicity. Some of these tested compounds were found to demonstrate significant cytotoxicity. The most potent compound (9-(3,4,5-trimethoxybenzyl)-9H-carbazol-3-yl)methanol (1d) demonstrated strong cytotoxic effect with IC50 values in 10-7 to 10-9 M against human leukemia cell HL-60, human hepatoma cell Hep3B, breast cancer cell MCF7, ovarian cancer cell 2774, SKOV3 and lung cancer cell H226, H460. Therefore compound 1d was selected for further investigation.
中文摘要…………………………………………………………………1
英文摘要…………………………………………………………………2
第一章 緒論…………………………………………………………3
第一節 Carbazole類化合物之研究概況…………………………..3
第二節 Carbazole類化合物之合成方法…………………………..5
第三節 Carbazole類化合物之抗癌活性………………………….13
第四節 細胞週期之生命機制…………………………………….16
第二章 研究動機與目的…………………………………………..18
第三章 結果與討論 ………………………………………………21
第一節 化學合成概述………………………………………………21
第二節 藥理試驗結果………………………………………………33
第四章 結論…………………………………………………………41
第五章 實驗部分…………………………………………..………..42
第一節 試藥與溶媒…………………………………………...…….42
第二節 重要儀器與實驗材料…………………..…………………..44
第三節 化合物之合成………………………………………………46
第四節 藥理試驗方法………………………………………………86
參考文獻………………………………………………………………..88
附圖……………………………………………………………………..94
圖目錄
圖1-1 化合物1之MS圖譜………………………………………………...……….94
圖1-2 化合物1之IR圖譜………………………………………………….……….94
圖1-3 化合物1之1H-NMR圖譜 (DMSO-d6,200 MHz)……………………………95
圖1-4 化合物1之13C-NMR圖譜 (DMSO-d6,200 MHz)...........................................95
圖1a-1 化合物1a之MS圖譜……………………………………............................96
圖1a-2 化合物1a之IR圖譜…………………………………………..........…...….96
圖1a-3 化合物 1a之1H-NMR圖譜 (DMSO-d6,200 MHz)......................................97
圖1a-4 化合物 1a之13C-NMR圖譜 (DMSO-d6,200 MHz).....................................97
圖1a-5 化合物 1a之DEPT135圖譜 (DMSO-d6,200 MHz).........…….………......98
圖1a-6-1 化合物 1a之HMQC圖譜 (DMSO-d6,200 MHz)...................…………..98
圖1a-6-2 化合物 1a之HMQC圖譜 (DMSO-d6,200 MHz)....................………….99
圖1a’-1 化合物1a’之MS圖譜………………………………………......................99
圖1a’-2 化合物1a’之IR圖譜…………………………………………………….100
圖1a’-3 化合物 1a’之1H-NMR圖譜 (DMSO-d6,200 MHz)…………………….100
圖1a’-4 化合物 1a’之13C-NMR圖譜 (DMSO-d6,200 MHz)……………………101
圖1b-1 化合物1b之MS圖譜…………………………………………………….101
圖1b-2 化合物1b之IR圖譜………………………………………...…………….102
圖1b-3 化合物 1b之1H-NMR圖譜 (DMSO-d6,200 MHz)………...…………....102
圖1b-4 化合物 1b之13C-NMR圖譜 (DMSO-d6,200 MHz)……….....………….103
圖1c-1 化合物1c之MS圖譜……………………………………………………...103
圖1c-2 化合物1c之IR圖譜…………………………………………………….…104
圖1c-3 化合物 1c之1H-NMR圖譜 (DMSO-d6,200 MHz)…………………...….104
圖1c-4 化合物 1c之13C-NMR圖譜 (DMSO-d6,200 MHz)………………...……105
圖1d-1 化合物1d之MS圖譜……………………………………………………..105
圖1d-2 化合物1d之IR圖譜……………………………………………………..106
圖1d-3 化合物 1d之1H-NMR圖譜 (DMSO-d6,200 MHz)…………………...…106
圖1d-4 化合物 1d之13C-NMR圖譜 (DMSO-d6,200 MHz)…………………….107
圖1e-1 化合物1e之MS圖譜……………………………………………………..107
圖1e-2 化合物1e之IR圖譜………………………………………………………108
圖1e-3 化合物 1e之1H-NMR圖譜 (DMSO-d6,200 MHz)…………………...….108
圖1e-4 化合物 1e之13C-NMR圖譜 (DMSO-d6,200 MHz)……………………..109
圖1f-1 化合物1f之MS圖譜………………………………………………………109
圖1f-2 化合物1f之IR圖譜……………………………………………………….110
圖1f-3 化合物 1f之1H-NMR圖譜 (DMSO-d6,200 MHz)……………………….110
圖1f-4 化合物 1f之13C-NMR圖譜 (DMSO-d6,200 MHz)………………………111
圖1g-1 化合物1g之MS圖譜…………………………………………………….111
圖1g-2 化合物1g之IR圖譜………………………………………………………112
圖1g-3 化合物 1g之1H-NMR圖譜 (DMSO-d6,200 MHz)………………………112
圖1g-4 化合物 1g之13C-NMR圖譜 (DMSO-d6,200 MHz)………. …………….113
圖2-1 化合物2之MS圖譜………………………………………………….…….113
圖2-2 化合物2之IR圖譜…………………………………………………………114
圖2-3 化合物 2之1H-NMR圖譜 (DMSO-d6,200 MHz)…………………………114
圖2-4 化合物 2之13C-NMR圖譜 (DMSO-d6,200 MHz)…….………………..…115
圖2a-1 化合物2a之MS圖譜…………………………………………………….115
圖2a-2 化合物2a之IR圖譜………………………………………………………116
圖2a-3 化合物 2a之1H-NMR圖譜 (DMSO-d6,200 MHz)...............…………….116
圖2a-4 化合物 2a之13C-NMR圖譜 (DMSO-d6,200 MHz).............……………..117
圖2d-1 化合物2d之MS圖譜……………………………………………………..117
圖2d-2 化合物2d之IR圖譜………………………………………………………118
圖2d-3 化合物 2d之1H-NMR圖譜 (DMSO-d6,200 MHz)...................………….118
圖2d-4 化合物 2d之13C-NMR圖譜 (DMSO-d6,200 MHz)................…………..119
圖2d-5 化合物 2d之DEPT135圖譜 (DMSO-d6,200 MHz)…………………..…119
圖3-1 化合物3之MS圖譜………………………………………………………..120
圖3-2 化合物3之IR圖譜…………………………………………………………120
圖3-3 化合物 3之1H-NMR圖譜 (DMSO-d6,200 MHz)…………………………121
圖3-4 化合物 3之13C-NMR圖譜 (DMSO-d6,200 MHz).................……………..121
圖3a-1 化合物3a之MS圖譜…………………………………………………….122
圖3a-2 化合物3a之IR圖譜………………………………………………………122
圖3a-3 化合物 3a之1H-NMR圖譜 (DMSO-d6,200 MHz)...............…………….123
圖3a-4 化合物 3a之13C-NMR圖譜 (DMSO-d6,200 MHz).........………………..123
圖3a-5 化合物 3a之DEPT135圖譜 (DMSO-d6,200 MHz)..………………........124
圖3a-6-1 化合物 3a之HMQC圖譜 (DMSO-d6,200 MHz).……………..............124
圖3a-6-2 化合物 3a之HMQC圖譜 (DMSO-d6,200 MHz)………………...........125
圖3a-7-1 化合物 3a之HMBC圖譜 (DMSO-d6,200 MHz).....………………......125
圖3a-7-2 化合物 3a之HMBC圖譜 (DMSO-d6,200 MHz)………………...........126
圖3d-1 化合物3d之MS圖譜…………….……………………………………….126
圖3d-2 化合物3d之IR圖譜………………………………………………………127
圖3d-3 化合物 3d之1H-NMR圖譜 (DMSO-d6,200 MHz)……………...………127
圖3d-4 化合物 3d之13C-NMR圖譜 (DMSO-d6,200 MHz)………………..……128
圖4-1 化合物4之MS圖譜……………………………………………………….128
圖4-2 化合物4之IR圖譜…………………………………………...…………….129
圖4-3 化合物 4之1H-NMR圖譜 (DMSO-d6,200 MHz)…………………………129
圖4-4 化合物 4之13C-NMR圖譜 (DMSO-d6,200 MHz)..............……………….130
圖4-5 化合物 4之DEPT135圖譜 (DMSO-d6,200 MHz).........……………….....130
圖4a-1 化合物4a之MS圖譜………………………………………………...…...131
圖4a-2 化合物4a之IR圖譜……………………………………………………..131
圖4a-3 化合物 4a之1H-NMR圖譜 (DMSO-d6,200 MHz)...........……………….132
圖4a-4 化合物 4a之13C-NMR圖譜 (DMSO-d6,200 MHz).....………………......132
圖4a-5 化合物 4a之DEPT135圖譜 (DMSO-d6,200 MHz)……………..............133
圖4a-6-1 化合物 4a之HMQC圖譜 (DMSO-d6,200 MHz).......…………...........133
圖4a-6-2 化合物 4a之HMQC圖譜 (DMSO-d6,200 MHz).........…………..........134
圖4d-1 化合物4d之MS圖譜……………………………………………………..134
圖4d-2 化合物4d之IR圖譜……………………………………………………....135
圖4d-3 化合物 4d之1H-NMR圖譜 (DMSO-d6,200 MHz)..............…………….135
圖4d-4 化合物 4d之13C-NMR圖譜 (DMSO-d6,200 MHz)..........……………....136
圖4d-5 化合物 4d之DEPT135圖譜 (DMSO-d6,200 MHz).......…………….......136
圖5-1 化合物5之MS圖譜……………………………………………….……….137
圖5-2 化合物5之IR圖譜………………………………………………….……...137
圖5-3 化合物 5之1H-NMR圖譜 (DMSO-d6,200 MHz)…………………………138
圖5-4 化合物 5之13C-NMR圖譜 (DMSO-d6,200 MHz)……………………….138
圖5a-1 化合物5a之MS圖譜………………………………………………….….139
圖5a-2 化合物5a之IR圖譜………………………………………………………139
圖5a-3 化合物 5a之1H-NMR圖譜 (DMSO-d6,200 MHz)...............…………….140
圖5a-4 化合物 5a之13C-NMR圖譜 (DMSO-d6,200 MHz).............……………..140
圖5d-1 化合物5d之MS圖譜……………………………………………………..141
圖5d-2 化合物5d之IR圖譜………………………………………...…………….141
圖5d-3 化合物 5d之1H-NMR圖譜 (DMSO-d6,200 MHz).............……………..142
圖5d-4 化合物 5d之13C-NMR圖譜 (DMSO-d6,200 MHz)............……………..142
圖5d-5 化合物 5d之DEPT135圖譜 (DMSO-d6,200 MHz).........…………….....143
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