Design, Synthesis, and Structure–Activity Relationship of New 2-Aryl-3,4-dihydro-β-carbolin-2-ium Salts as Antifungal Agents

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• 作者：Zhe Hou ; Li-Fei Zhu ; Xin-chi Yu ; Ma-Qiang Sun ; Fang Miao ; Le Zhou
• 刊名：Journal of Agricultural and Food Chemistry
• 出版年：2016
• 出版时间：April 13, 2016
• 年：2016
• 卷：64
• 期：14
• 页码：2847-2854
• 全文大小：374K
• 年卷期：0
• ISSN：1520-5118

文摘

Twenty-two 2-aryl-9-methyl-3,4-dihydro-β-carbolin-2-ium bromides along with four 9-demethylated derivatives were synthesized and characterized by spectroscopic analysis. By using the mycelium growth rate method, the compounds were evaluated for antifungal activities in vitro against six plant pathogenic fungi, and structure–activity relationships (SAR) were derived. Almost all of the compounds showed obvious inhibition activity on each of the fungi at 150 μM. For all of the fungi, 10 of the compounds showed average inhibition rates of >80% at 150 μM, and most of their EC₅₀ values were in the range of 2.0–30.0 μM. SAR analysis showed that the substitution pattern of the N-aryl ring significantly influences the activity; N₉-alkylation improves the activity, whereas aromatization of ring-C reduces the activity. It was concluded that the present research provided a series of new 2-aryl-9-alkyl-3,4-dihydro-β-carbolin-2-iums with excellent antifungal potency and structure optimization design for the development of new carboline antifungal agents.