萘醌(Naphthoquinone)的結構常見於許多天然藥物以及有療效的藥物中,鑒於其衍生物優異的生物活性,我們在本篇論文中以2-羥基-1,4-萘醌(2-Hydroxy-[1,4]naphthoquinone)、萘酚(Naphthol)做為起始物與疊氮化合物(Azide)形成三唑(Triazole)的雜環化合物,以高效率、低毒性、溫和的條件,經由環化加成並脫水的方式,以獲得高產率的Naphtho [2,3-d] [1,2,3] triazole-4,9-dione產物,此方法有別於傳統的CuAAC (Copper Catalyzed Azide-Alkyne Cycloadditions),其合成路徑簡單且具有經濟效益及環境保護性。 另一方面,在初步的體外細胞活性測試中(in vitro),發現對A375(皮膚癌細胞)、A2058(皮膚癌細胞)、B16(老鼠皮膚癌細胞,黑色素瘤)以及H1299(肺腺癌細胞),表現出相當不錯的抗癌活性。
Napthaquinones are important class of biologically active compounds found in natural and pharmaceutical drugs. In this thesis, the novel synthetic strategy to construct naphtho[2,3-d][1,2,3]triazole-4,9-dione derivatives via a cycloaddition derived from versatile starting material such as 2-hydroxy -1,4-napthaquinone and Naphthol was reported. This synthetic approach differs from traditional CuAAC (Copper Catalyzed Azide-Alkyne Cycloadditions) chemistry and has several key features such as metal free, atom economy, and eco-friendly process. On the other hand, the new products of our synthesis was assay by MTT assay (in vitro), which NP-4ME show the best antitumor activity against melanoma.