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研究生:侯曼貞
研究生(外文):Mann-Jen Hour
論文名稱:6,7,2',3',4',5'-取代-2-苯基-4-■唑■酮類衍生物之合成、細胞致毒活性及抗血小板活性
論文名稱(外文):Synthesis, Cytotoxicity and Antiplatelet Activity of 6,7,2',3',4',5'-Substituted 2-phenyl-4-quinazolinone Derivatives
指導教授:郭盛助郭盛助引用關係黃麗嬌黃麗嬌引用關係
指導教授(外文):Sheng-Chu KuoLi-Jiau Huang
學位類別:博士
校院名稱:中國醫藥學院
系所名稱:藥物化學研究所
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:2000
畢業學年度:88
語文別:中文
論文頁數:218
中文關鍵詞:2-苯基-4-■唑■酮類衍生物細胞致毒活性抗血小板活性合成
外文關鍵詞:2-phenyl-4-quinazolinone DerivativesCytotoxicityAntiplatelet ActivitySynthesis
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在繼續找尋2-苯基-4-■唑■酮及2-苯基-4-■■酮類中具有抗癌開發潛能化合物的過程中,本研究合成了一系列6,7,2',3',4',5'-取代-2-苯基-4-■唑■酮及6,2',3',4',5'-取代-2,3-雙氫-2-苯基-4-■唑■酮類衍生物,並進行對抗人類腫瘤細胞之致毒活性及抑制微管蛋白聚合作用的評估,經由這些生物活性的篩選試驗,建立了初步的結構與活性關係,並發現在細胞致毒活性與抑制微管蛋白聚合活性這兩者之間大都具有關連性。其中,6-雜環-2-苯基-4-■唑■酮類衍生物 (56-60) 具有優越的細胞致毒活性,其半數致效濃度 (EC50) 在微莫耳 (mM) 至微毫莫耳 (nM) 濃度之間。尤以2-(3'-甲氧苯基)-6-(■咯啶基)-4-■唑■酮 (57) 之細胞致毒活性最為優越,同時,化合物57也是強效的微管蛋白聚合抑制劑,其活性幾乎與秋水仙鹼、普多非倫毒及combretastatin A-4等天然抗癌物質相當。6,7,2',3',4',5'-取代-2-苯基-4-■唑■酮及6,2',3',4',5'-取代-2,3-雙氫-2-苯基-4-■唑■酮類衍生物對於卵巢癌 (1A9) 及對於vincristine產生抗藥性之鼻咽表皮樣癌 (KB-VIN) 也具有高度選擇性的細胞致毒活性。
另一方面,將2-苯基-4-■唑■酮及2-苯基-4-■■酮類化合物進行烷基化反應,合成一系列4-烷氧基-2-苯基■唑■及4-烷氧基-2-苯基■■類衍生物,並進行抗血小板活性評估。其中,4-乙氧基-2-苯基■唑■(71)、4-甲氧基-2-苯基■■(92)、4-乙氧基-2-苯基■■(93) 及7-氟-4-甲氧基-2-苯基■■(98) 對花生四烯酸所誘導之血小板凝集具有相當強的抑制作用,其活性約為阿司匹靈的10-13倍。
因此,我們將細胞致毒活性特別優越的化合物57及抗血小板活性特別優越的化合物71提供做進一步的藥理機轉研究。

As part of our continuing search for potential anticancer candidates of 2-phenyl-4-quinazolinones and 2-phenyl-4-quinolones, two series of 6,7,2',3',4',5'-substituted 2-phenyl-4-quinazolinones and 6,2',3',4',5'-substituted 2,3-dihydro-2-phenyl-4-quinazolinones have been synthesized and evaluated for cytotoxicity and inhibition of tubulin polymerization. Through these biological screening, a preliminary structure-activity relationship has been established. On the whole, a good correlation was found between the two activities. Among them, 6-N,N-dimethylamino and 6-heterocyclic 2-phenyl-4-quinazolinones (56-60) showed potent cytotoxicity against a panel of human tumor cell lines with EC50 values in the low micromolar to nanomolar concentration ranges. 2-(3'-Methoxyphenyl)-6-(pyrrolidinyl)-4-quinazolinone (57) was especially the most potent. Moreover, compound 57 was also a potent inhibitor of tubulin polymerization with activity comparable to that of the antimitotic natural products such as colchicine, podophyllotoxin, and combretastatin A-4. Substituted 2-phenyl-4-quinazolinones and 2,3-dihydro-2-phenyl-4-quinazolinones also displayed highly selective cytotoxicity against the ovarian cancer (1A9) and vincristine-resistant epidermoid carcinoma of the nasopharynx (KB-VIN).
On the other hand, a series of 4-alkoxy-2-phenylquinazolines and 4-alkoxy-2-phenylquinolines were synthesized respectively via alkylation of 2-phenyl-4-quinazolinones and 2-phenyl-4-quinolones, and their antiplatelet activities were evaluated. Among them, 4-ethoxy-2-phenylquinazoline (71), 4-methoxy-2-phenylquinoline (92), 4-ethoxy-2-phenylquinoline (93) and 7-fluoro-4-methoxy-2-phenylquinoline (98) showed very potent inhibitory effects on the platelet aggregation induced by arachidonic acid. Their activities were about ten to thirteen times more potent than aspirin.
Compound 57 and 71, which exhibited strong cytotoxicity and antiplatelet activity respectively, were thus selected for further investigation of pharmaceutical mechanism.

封面
謝辭
目錄
中文摘要
英文摘要
第一章 緒論
第一節 Quinazolinone類緣化合物之研究概況
第二節 抗癌藥物之概述
第三節 抗血小板藥物之概述
第四節 研究動機與目的
第二章 結果與討論
第一節 化學合成
I. 原料製備
I-1. 2-Amino-5-fluorobenzamide (3) 之合成
I-2. 2-Amino-4,5-substituted benzamides (10, 11, 16) 之合成
I-3. 2-Amino-5-alkylaminobenzamides (25-29) 之合成
II. 標的化合物之合成
II-1. 6,7,2',3',4',5'-Substituted 2-phenyl-4-quinazolinones (41-60)之合成
II-2. 6,2',3',4',5'-Substituted 2,3-dihydro-2-phenyl-4- quinazolinones (61-69) 之合成
II-3. 4-Alkoxy-2-phenylquinazolines (70-79) 及N-alkyl-2-phenylquinazolinones ( 80-86) 之合成
II-4. 4-Alkoxy-2-phenylquinolines (92-99) 及N-alkyl-2-phenylquinolones (100- 104)之合成
第二節 細胞致毒活性
第三節 抑制微管蛋白聚合活性
第四節 抗血小板活性
第三章 結論
第四章 實驗部分
第一節 試藥、溶媒與材料
第二節 重要儀器
第三節 化學合成方法
第四節 藥理試驗方法
參考文獻
已投稿論文
專利申請
圖次

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