| 摘要: |
| 【目的】寻找具有高抑菌活性的新型化合物。【方法】以 3-吲哚乙腈为原料，经过1-位烷基化、2-位氧化和3-位烷基化反应，合成1,3-二取代-2-氧代-3-吲哚乙腈类衍生物，对合成的化合物进行核磁共振谱(1H NMR、13C NMR)和低分辨质谱(LC-ESI-MS)分析，并分别测定合成衍生物对-5-种供试病原真菌(小麦赤霉病菌、茄子黄萎病菌、烟草赤星病菌、番茄灰霉病菌、苹果炭疽病菌) 的抑菌活性。【结果】经1H NMR、13C NMR和LC-ESI-MS分析确认，成功合成了6个1,3-二取代-2-氧代-3-吲哚乙腈类衍生物 (3a~3f)。抑菌活性试验结果表明，6个目标化合物对5种供试病原真菌均有一定的抑菌活性；结构与活性相关分析说明，此类化合物骨架中芳香苄基对抑菌活性的贡献优于脂肪烃基异戊烯基，且芳香苄基中氟原子对化合物的抑菌活性有一定的促进作用，其中1-位和3-位同为对氟苄基的化合物3f(1,3-二对氟苄基-2-氧代-3-吲哚乙腈)，对番茄灰霉病菌和烟草赤星病菌均具有较高的抑菌活性，有效中浓(EC50)分别为28.06和31.36 μg/mL。【结论】本研究的合成方法简单、高效，合成的化合物3e和3f对5种供试病原真菌的抑菌活性均高于其他化合物，具有进一步研究和开发的价值。 |
| 关键词: 3-吲哚乙腈 1,3-二取代-2-氧代-3-吲哚乙腈衍生物 抑菌活性 |
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| 基金项目:国家自然科学基金项目 (31201549)； 陕西省自然科学基金项目 (2016JM3035) |
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| Synthesis and antifungal activity of 1,3-disubstitued-2-oxo-3-indolylacetonitrile derivatives |
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MA Miaofeng,WANG Dezhi,XIA Xianhua,et al
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| Abstract: |
| 【Objective】The purpose of this study was to synthesize novel compounds with fungicidal activities. 【Method】 Six 1,3-disubstitued-2-oxo-3-indolylacetonitrile derivatives were synthesized using 3-indolylacetonitrile as starting material through 1-alkylation,2-oxidation and 3-alkylation reactions.All synthesized compounds were confirmed by 1H NMR、13C NMR and LC-ESI MS.Their in vitro antifungal activities were evaluated against five phytopathogenic fungi using the mycelium growth rate method.【Result】 Six 1,3-disubstitued-2-oxo-3-indolylacetonitrile derivatives were successfully synthesized,and the target compounds were found to have antifungal activities against all the five tested phytopathogenic fungi.Analysis of the structure activity revealed that benzyl group on the scaffold had more contribution to fungicidal activity than prenyl group.Especially,compound 3f with p fluoro benzyl at C-1 and C-3 positions showed high antifungal activities against Botrytis cinerea and Alternaria alternata with EC50 values of 28.06 and 31.36 μg/mL,respectively. 【Conclusion】 This synthetic approach was simple and efficient with high yields.Compounds 3e and 3f displayed higher activities against the five tested phytopathogenic fungal than other synthesized compounds,and could be further explored to develop potent antifungal agents. |
| Key words: 3-indolylacetonitrile 1,3-disubstitued-2-oxo-3-indolylacetonitrile derivatives antifungal activity |
