合成特殊的氨黃酮化合物及探討單吲哚馬來醯亞胺類化合物的合成方法

Syntheses of Unique Aminoflavones and Asymmetric Indolymaleimide Frameworks

周祺恩(Chi-En Chou)

指導教授 ： 施增廉

淡江大學/理學院/化學學系碩士班/碩士(2013年)

https://doi.org/10.6846/TKU.2013.00022

摘要

類黃酮化合物 (flavonoids) 具有良好的生物活性，如:自由基清除劑、金屬離子螯合劑、氧化酶抑制劑，甚至可做為抗癌藥物而倍受關注。
本論文選擇以黃酮類為主要結構並合成氨黃酮為目標。天然或合成的氨黃酮類非常稀少，而傳統製備氨黃酮的方式，是先合成硝基後再還原成氨基。然而我選用具鹵素之苯環起始物，所需合成步驟為耦合反應、貝克-文卡塔拉曼重排反應、酸催化合環反應可順利製備黃酮化合物的主體結構，再將其鹵素官能基經由 Cu金屬催化置換成氨基，成功發展出新的氨黃酮製備方法。
另外，單吲哚馬來醯亞胺化合物已被研究證明具有抑制蛋白激酶C的活性，此激酶與癌症的控制有很大的關係，因此學術界與業界希望將單吲哚馬來醯亞胺化合物發展成有效的抗癌藥物。
先利用文獻方式架構單邊的吲哚馬來醯亞胺化合物，再利用Pd金屬催化耦合反應，並比較微波與傳統加熱方式對產率的影響。我們所合成的單吲哚馬來醯亞胺化合物結構目前還未被報導過，未來可望有更好的生物活性。

關鍵字

氨黃酮 ； 單吲哚馬來醯亞胺

並列摘要

Flavonoids possess various kinds of biological activities. They are commonly used for reactive oxygen species scavengers, metal chelators, oxidase inhibitors, and anticancer drugs, etc.
We employed flavones as the main framework to synthesize aminoflavones. The conventional method in preparation of aminoflavones were derived from the reduction of nitroflavones or deacetylation of amides. In this article, we applied via coupling reaction, Baker-Venkataraman rearrangement, and acid-catalyzed cyclization to synthesize the framework of flavones. Subsequently, we replaced the halogen group with amino group medidated by copper powder.
In addition, indolymaleimides have been reported that they could inhibited protein kinase C activity. These isoenzymes are believed to control the cancer growth and proliferations. Therefore, we wish to synthesize more effective anticancer drugs.
Asymmetric indolymaleimide compounds were synthesized from monosubstituted indolymaleimide with benzoxazoles, and we compared yields between microwave and conventional heating. These indolymaleimides have not yet been reported.

並列關鍵字

Aminoflavone ； Indolymaleimide

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