萘并[2,3-d]咪唑-4,9-二酮衍生物之合成與抗增生活性評估

Synthesis and Antiproliferative Evaluation of Naphtho[2,3-d]imidazole-4,9-dione Derivatives

謝皓宇(Hao-Yu Hsieh)

指導教授 ： 曾誠齊

高雄醫學大學/生命科學院/醫藥暨應用化學研究所/碩士(2010年)

https://doi.org/10.6832/KMU.2010.00134

摘要

本研究為描述萘并[2,3-b]呋喃-4,9-二酮衍生物之合成以及抗增生活性評估。我們合成了一系列在N-1，C-2，C-4位置上有取代的衍生物，並研究此衍生物抗增生活性結構活性和衍生物之取代機種類與取代基位置之關聯性。最初的結果顯示，(E)-1-cyclopropyl-4,9-dioxo-4,9-dihydro-naphtho[2,3-d] imidazole-2-carbaldehyde O-2-(piperidin-1-yl)ethyl oxime (20), (Z)-N-(4-(1-ethyl-2-methyl-9-oxo-naphtho[2,3-d]imidazol-ylideneamino-phenyl)acetamide (21d), (Z)-4-(1-cyclopropyl-2-methyl-9-oxo-naphtho[2,3-d]imidazol- ylideneamino)-N-(2-(diethylamino)ethyl)benzamide (21e)與及1-(3-(Dimethylamino)propyl)-2-(furan-2-yl)-1H-naphtho[2,3-d]imidazole-4,9- dione (25e)，並展現出對於A549細胞株具有選擇性抑制活性，其GI50值為6.40，6.93和6.48μM。(25e)對CE81T細胞株的GI50值為4.78μM。

關鍵字

合成 ； 咪唑 ； 抗增生活性

並列摘要

This thesis describes synthesis and antiproliferative evaluation of naphtho[2,3-b]furan-4,9-dione derivatives. A number of substituents have been introduced on the N-1, C-2, or C-4 position to investigate the antiproliferative structure activity relationship with respect to the kind of substituents and the position of substitution. Preliminary results indicated that (E)-1-cyclopropyl-4,9-dioxo-4,9-dihydro-naphtho[2,3-d]imidazole- 2-carbaldehyde O-2-(piperidin-1-yl)ethyl oxime (20), (Z)-N-(4-(1-ethyl-2-methyl-9-oxo-naphtho[2,3-d]imidazol-ylideneamino- phenyl)acetamide (21d), and (Z)-4-(1-cyclopropyl-2-methyl-9-oxo- naphtho[2,3-d]imidazol-ylideneamino)-N-(2-(diethylamino)ethyl)benzamide (21e) , 1-(3-(Dimethylamino)propyl)-2-(furan-2-yl)-1H-naphtho[2,3-d]imidazole -4,9- dione (25e) exhibited selective inhibitory activity against the growth of A549 cancer cell line with GI50 value of 6.40, 6.93, and 6.48 ?嵱 respectively. Compound (25e) of the CE81T cell lines GI50 value is 4.78μM

並列關鍵字

imidazole ； synthesis ； antiproliferative

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