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| ???org.dspace.app.webui.jsptag.ItemTag.dcfield??? | Value | Language |
|---|---|---|
| dc.contributor.advisor | 陳基旺 | |
| dc.contributor.author | Yin-Ling Wei | en |
| dc.contributor.author | 魏吟玲 | zh_TW |
| dc.date.accessioned | 2021-06-08T05:23:05Z | - |
| dc.date.copyright | 2005-08-18 | |
| dc.date.issued | 2005 | |
| dc.date.submitted | 2005-07-25 | |
| dc.identifier.citation | Information received from the Internet Homepages of the Department of Health, Taiwan, R.O.C.(http://www.doh.gov.tw).
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| dc.identifier.uri | http://tdr.lib.ntu.edu.tw/jspui/handle/123456789/24357 | - |
| dc.description.abstract | 本論文主旨為設計與合成喹啉（quinoline）衍生物作為潛能癌細胞毒殺劑，主要內容為合成3-phenylquinolines（7-10）與2-phenylquinolines（11-14、17與18）兩系列目標化合物，並評估其癌細胞毒殺活性。3-Phenylquinolines 7-10的製備，先由8-nitroquinoline與N-bromosuccinimide（NBS）在第3位進行溴化反應後，經Suzuki耦合反應可得到中間物8-nitro-3-phenylquinoline（1a）與3-(4-methoxyphenyl)- 8-nitroquinoline（1b）。將中間物1a,b使用鐵粉還原後，再與不同取代的benzenesulfonyl chloride、benzoyl chloride或phenyl isocyanate進行反應可得到目標化合物7-10。為了製備第8位取代之2-phenylquinoline 11-14，首先由o-nitroaniline與不同取代的桂皮醛於酸性條件下進行Doebner-Miller環化反應得到中間物8-nitro-2-phenylquinoline（2a）與2-(4-methoxyphenyl)-8-nitroquinoline（2b）。此外，第6位取代2-phenylquinoline 17與18的製備，先取不同取代的acetophenones與Vilsmeier-Haack試劑（POCl3/DMF）反應，接著與兩當量p-nitroaniline作用，最後在220-250 ℃下進行環化反應得到中間物6-nitro-2-phenylquinoline（3a）與2-(4-methoxyphenyl)-6-nitroquinoline（3b）。利用1a,b之相同序列反應，取中間物2a,b與3a,b製備目標化合物11-14、17與18。所有目標化合物經使用MTT分析法對胃癌細胞株（AGS）、肺癌細胞株（A549）、肝癌細胞株（HepG2）、大腸直腸癌細胞株（HT-29）與前列腺癌細胞株（PC-3）進行體外（in vitro）癌細胞毒性測試，結果顯示化合物7a-c、8a,b、10a,b、11b,c、12b、13a,b及14a,b對某些癌細胞株呈現有意義的抑制活性，其GI50（PC-3為IC50）在low micromolar與submicromolar濃度層級之間。其中活性呈現較強的化合物，在肝癌細胞中，7a、7c、8a與8b之GI50分別為0.12、0.18、0.11及0.20 μM；在胃癌細胞中，7a與8a之GI50分別為0.73及1.03 μM；在大腸直腸癌細胞中，11b之GI50為0.55 μM。進一步經流式細胞儀分析，發現7a與8a會使胃癌與肝癌細胞停滯在S與G2/M期；7c與8b會使肝癌細胞停滯在S與G2/M期，並誘導癌細胞走向細胞凋亡；11b會使得大腸直腸癌細胞停滯在G2/M期，且誘導癌細胞走向細胞凋亡。依據生物活性分析結果顯示此類具第8位苯磺醯胺基取代之3-苯基與2-苯基喹啉衍生物可作為發展新型抗癌藥物之先導化合物。 | zh_TW |
| dc.description.abstract | The aim of this thesis is to design and synthesize quinoline derivatives as potential cytotoxic agents. Two series of target compounds, 3-phenylquinolines (7-10) and 2-phenylquinolines (11-14, 17 and 18), were prepared and evaluated for their cytotoxicity. In the preparation of 3-phenylquinolines 7-10, the required intermediates 8-nitro-3-phenylquinoline (1a) and 3-(4-methoxyphenyl)-8-nitroquinoline (1b) were obtained from 8-nitroquinoline by bromination with N-bromosuccinimide (NBS) followed by Suzuki coupling reaction. Reduction of the nitro compounds 1a,b with iron powder and subsequent reaction with appropriate benzenesulfonyl chloride, benzoyl chloride or phenyl isocyanate provided target compounds 7-10. To prepare target 8-substituted 2-phenylquinolines 11-14, o-nitroaniline was reacted with appropriate cinnamaldehyde under acidic conditions via Doebner-Miller cyclization to give the intermediates 8-nitro-2-phenylquinoline (2a) and 2-(4-methoxyphenyl)-8-nitroquinoline (2b). The intermediates 6-nitro-2-phenylquinoline (3a) and 2-(4-methoxyphenyl)-6-nitroquinoline (3b) for the synthesis of target 6-substituted 2-phenylquinolines 17 and 18 were prepared from appropriate acetophenone by treatment with Vilsmeier-Haack reagent (POCl3/DMF), followed by reaction with 2 equivalents of p-nitroaniline and subsequent cyclization at 220-250 ℃. The intermediates 2a,b and 3a,b were subjected to the same sequence of reactions as performed on 1a,b to provide target compounds 11-14, 17 and 18. All target compounds were evaluated for in vitro antiproliferative activity against five human tumor cell lines (AGS, A549, HepG2, HT-29 and PC-3) by MTT assay. Among the tested compounds, 7a-c, 8a,b, 10a,b, 11b,c, 12b, 13a,b and 14a,b demonstrated significant cytotoxicity against certain cell lines with GI50 (IC50 for PC-3) values in the low micromolar to submicromolar concentration range. The present investigation has led to the discovery of some promising cytotoxic compounds with good potency as follows: 7a, 7c, 8a and 8b (for HepG2 cell line, GI50 = 0.12, 0.18, 0.11 and 0.20 μM, respectively); 7a and 8a (for AGS cell line, GI50 = 0.73 and 1.03 μM, respectively); 11b (for HT-29 cell line, GI50 = 0.55 μM). Furthermore, as revealed from the results obtained in flow cytometry analyses, compounds 7a and 8a caused S and G2/M arrests in AGS and HepG2 cells; compounds 7c and 8b caused S and G2/M arrests and induced apoptosis in HepG2 cells; and compound 11b caused G2/M arrest and induced apoptosis in HT-29 cells. These results suggest that the designed 8-benzenesulfonamido substituted 3-phenylquinolines and 2-phenylquinolines may serve as useful lead compounds for the development of new antitumor agents. | en |
| dc.description.provenance | Made available in DSpace on 2021-06-08T05:23:05Z (GMT). No. of bitstreams: 1 ntu-94-R92423004-1.pdf: 1086913 bytes, checksum: aec3c14d9e4d1f3b4c8f0a962affa75c (MD5) Previous issue date: 2005 | en |
| dc.description.tableofcontents | 壹、緒論 1
貳、實驗目的與設計 14 叁、結果與討論 17 3.1 目標化合物之合成策略 17 3.2 目標化合物之合成 19 3.2.1 8-Substituted 3-phenylquinolines 7-10之合成 19 3.2.2 8-Substituted 2-phenylquinolines 11-14之合成 25 3.2.3 6-Substituted 2-phenylquinolines 17與18之合成 27 3.3 生物活性測試 29 3.3.1 硝基化合物1-3之體外活性測試 29 3.3.2 8-Substituted 3-phenylquinolines之體外活性測試 30 3.3.3 8-Substituted 2-phenylquinolines之體外活性測試 32 3.3.4 6-Substituted 2-phenylquinolines之體外活性測試 33 3.4 作用機制探討 34 肆、結論 39 伍、實驗部分 40 5.1 實驗儀器與檢驗方法 40 5.2 試藥、溶劑 40 5.3 合成步驟 41 5.4 生物活性評估 59 陸、參考文獻 63 | |
| dc.language.iso | zh-TW | |
| dc.subject | 苯磺醯胺 | zh_TW |
| dc.subject | 苯基喹 | zh_TW |
| dc.subject | 衍生物 | zh_TW |
| dc.subject | 癌細胞毒殺劑 | zh_TW |
| dc.subject | phenylquinoline | en |
| dc.subject | cytotoxic agent | en |
| dc.subject | benzenesulfonamide | en |
| dc.title | 喹啉衍生物作為癌細胞毒殺劑之設計與合成 | zh_TW |
| dc.title | Design and Synthesis of Quinoline Derivatives as Potential Cytotoxic Agents | en |
| dc.type | Thesis | |
| dc.date.schoolyear | 93-2 | |
| dc.description.degree | 碩士 | |
| dc.contributor.oralexamcommittee | 王光昭,顧記華,孔繁璐,陳香惠 | |
| dc.subject.keyword | 苯基喹,啉,衍生物,癌細胞毒殺劑,苯磺醯胺, | zh_TW |
| dc.subject.keyword | phenylquinoline,cytotoxic agent,benzenesulfonamide, | en |
| dc.relation.page | 69 | |
| dc.rights.note | 未授權 | |
| dc.date.accepted | 2005-07-26 | |
| dc.contributor.author-college | 醫學院 | zh_TW |
| dc.contributor.author-dept | 藥學研究所 | zh_TW |
| Appears in Collections: | 藥學系 | |
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