薑黃素苯并呋喃衍生物之合成

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题名:	薑黃素苯并呋喃衍生物之合成 Synthesis of Benzofuran Derivatives of Curcumin
作者:	許文耀
贡献者:	化學系應用化學碩士班
关键词:	薑黃素 curcumin
日期:	2017
上传时间:	2017-08-10 13:45:12 (UTC+8)
摘要:	好幾個世紀以來薑黃一直被用於中藥之治療作用上，其根莖之成分為主要生物活性之一。薑黃素是從薑黃之根莖中提取得到的一種酚類化合物，具有廣泛的藥理活性，包含抗發炎、抗氧化和清除自由基等作用，奕有一些研究顯示其可用在治療阿茲海默氏症上。本論文中我們合成兩種系列之苯并呋喃環衍生物，其中一系列薑黃素苯并呋喃衍生物是以vanillin為起始物，當中利用Sonogashira方法進行末端炔與碘化苯環之cross-coupling反應，以Pd與Cu為催化劑，再經由環化反應，得到苯并呋喃環。另一系列衍生物是以o-vanillin為起始物，使用Rap-Stoermer方法與ethyl bromoacetate進行縮合反應，合成出苯并呋喃環。再藉由Vilsmeier 方法，進行甲醯化形成醛類化合物。最後含苯并呋喃環之芳香醛類化合物藉由Claisen-Schmidt condensation，分別與2,4-pentanedione和cyclohexanone進行縮合反應，製備出六種薑黃素苯并呋喃衍生物。 Turmeric has been used for centuries for the treatment of different pathologies in the traditional Chinese medicine. Curcumin is one of the phenolic compounds derived from rhizome of turmeric plant (Curcumin longa) and is one of the principal bioactive components of rhizomes. Several studies have reported that curcumin possesses a wide range of pharmacological properties including antioxidant, anti-inflammatory and free radical scavenging activities. Some research evidences indicated that curcumin can be used for the treatment of Alzheimer’s disease. In this thesis, we synthesized two series of the benzofuran derivatives. One series of derivatives started form vanillin. Sonogashira cross-coupling reaction was used. It employed palladium and copper catalysts to form a carbon–carbon bond between a terminal alkyne and an aryl iodide, which was followed by cyclization to give a benzofuran. The other series of derivatives starting form o-vanillin. The synthesis of benzofuran derivatives was accomplished by the Rap-Stoermer reaction between substituted salicylaldehydes and ethyl bromoacetate, which were folloued by Vilsmeier formylation to give a benzofurancarbadlehyde. Benzofurancarbadlehydes reacted with 2,4-pentanedione or cyclohexan- one via Claisen-Schmidt condensation to afford six curcumin benzofuran derivatives.
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