單芽與三芽氮異環碳烯之銀配位化合物

Monodentate and Tridentate N-heterocyclic Carbene Complexes of Silver

林宏儒(Hong-Ru Lin)

指導教授 ： 邱靜雯

國立臺灣大學/理學院/化學研究所/碩士(2012年)

https://doi.org/10.6342/NTU.2012.00432

摘要

氮異環碳烯金屬配位化合物有優異催化性質，近幾十年來一直是熱門的研究方向，而許多此類分子也被證實具有良好的生物可耐受性及抑制細菌生長等效用，分子與生物體作用機轉研究也開始展開，因此在生醫領域運用上，抗微生物及抗癌藥物發展可能性，吸引了各地化學家的研究興趣。
本論文設計與合成一系列氮異環碳烯之銀配位化合物分子，由5,6-diamino-N-alkyl-benzimidazoles為起始物，除了環分子氮上可以靈活的修飾取代基，其兩個氨基團可與酮基團合成成環的分子。我們將其與含雙酮基之乙二醛、acenaphthylene-dione、phenanthroline-dione合成出單芽氮異環碳烯之銀配位化合物。其中與phenanthroline-dione進行合成的分子10，雙吡啶(bipyridine)可與釕金屬配位形成三芽的配基(ligand)。此外與hexaketocyclohexane合成分子也可形成三芽配基。與之前其他研究單純修飾氮異環氮上取代基不同，藉著延伸芳香基本體的單芽氮異環碳烯之銀配位化合物，增加其脂溶性及特殊分子構型，能提供與以往不同的分子模型運用於生醫研究。而三芽的配基也可與金屬形成高分子聚合物的設計，擁有潛在的新穎生醫分子材料特性。

關鍵字

氮異環碳烯金屬配位化合物 ； 抗微生物性 ； 抗癌藥 ； 氮異環碳烯 ； 生醫

並列摘要

Due to their profound catalytic activity, N-heterocyclic carbene (NHC) metal complexes have been the focal point of intense research studies in recent years. Many metal NHCs have been identified as low-toxicity chemicals in humans, and their medical effects have been examined as well. Several carbene-metal complexes are found to be effective for biomedical applications. For example, NHC complexes of gold, ruthenium, and silver are active chemical components that can be discovered in commercial antitumor drugs or antimicrobial agents. In this work, several silver-NHC complexes possessing extended pi-systems have been prepared. We also demonstrated a versatile synthesis strategy for the annulation of aromatic moieties to 5,6-diamino-N-alkyl-benzimidazoles, precursors to NHCs, via condensation with designated diketo derivatives. By choosing the proper diketo species, we synthesized not only monomeric Ag NHCs, but also poly-NHC ligands that serve as potential candidates for the polymeric silver networks. These polymeric silver-carbene networks are envisioned to possess dual biomedical functions, namely, drug delivery carrier as porous host materials and active antibacterial agent after polymer degradation.

並列關鍵字

N-heterocyclic carbenes ； NHC silver complexes ； biomedical application ； drug ； antimicrobial

參考文獻

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