College of Materials, Chemistry and Chemical Engineering, Chengdu University of Technology, Chengdu, 610059, P. R. China.
College of Ecological Environment, Chengdu University of Technology, Chengdu, 610059, P. R. China.
Chem Biodivers. 2021 May;18(5):e2100106. doi: 10.1002/cbdv.202100106. Epub 2021 Apr 15.
In search of new environmentally friendly and effective antifungal agents, a series of 4-aminoquinolines bearing a 1,3-benzodioxole moiety were prepared and their structures were fully elucidated by spectroscopic analyses. The antifungal activities of all the target compounds against five phytopathogenic fungi were evaluated in vitro. The results revealed that most of the newly synthesized compounds exhibited obvious inhibitory activities at the concentration of 50 μg/mL. Among them, 6-(furan-2-yl)-N-(4-methylphenyl)-2H-[1,3]dioxolo[4,5-g]quinolin-8-amine hydrochloride (7m) displayed more promising antifungal potency with EC values of 10.3 and 14.0 μg/mL against C. lunata and A. alternate, respectively. Particularly, the EC value of 7m against C. lunata was 7.3-fold as potent as the standard azoxystrobin. There were some significant morphological alterations in the mycelia of C. lunata when treated with 7m at 50 μg/mL. Additionally, the preliminary structure-activity relationships (SARs) were also discussed. Thus, this study suggests that 4-aminoquinolines bearing a 1,3-benzodioxole moiety are interesting scaffolds for the development of novel antifungal agents.
为了寻找新的环保且有效的抗真菌剂，我们合成了一系列带有 1,3-苯并二恶茂部分的 4-氨基喹啉，并通过光谱分析充分阐明了它们的结构。所有目标化合物对五种植物病原真菌的体外抗真菌活性进行了评估。结果表明，大多数新合成的化合物在 50μg/mL 的浓度下表现出明显的抑制活性。其中，6-(呋喃-2-基)-N-(4-甲基苯基)-2H-[1,3]二氧杂环[4,5-g]喹啉-8-胺盐酸盐（7m）对 C. lunata 和 A. alternate 的 EC 值分别为 10.3 和 14.0μg/mL，显示出更有希望的抗真菌活性。特别是，7m 对 C. lunata 的 EC 值比标准药剂唑菌酯的活性高 7.3 倍。当用 7m 在 50μg/mL 处理 C. lunata 的菌丝时，会出现一些明显的形态改变。此外，还讨论了初步的构效关系（SARs）。因此，本研究表明，带有 1,3-苯并二恶茂部分的 4-氨基喹啉是开发新型抗真菌剂的有趣支架。
