School of Pharmacy, Lanzhou University, Lanzhou 730000, People's Republic of China.
J Agric Food Chem. 2021 Oct 20;69(41):12156-12170. doi: 10.1021/acs.jafc.1c05677. Epub 2021 Oct 8.
Enlightened from our previous work of structural simplification of quinine and innovative application of natural products against phytopathogenic fungi, lead structure 2,8-bis(trifluoromethyl)-4-quinolinol () was selected to be a candidate and its diversified design, synthesis, and antifungal evaluation were carried out. All of the synthesized compounds were evaluated for their antifungal activity against four agriculturally important fungi, , , and . Results showed that compounds , , , , , , , , , . and exhibited a good antifungal effect, especially had the most potent activity with EC values of 0.52 and 0.50 μg/mL against and , respectively, which were more potent than those of the lead compound (1.72 and 1.89 μg/mL) and commercial fungicides azoxystrobin (both >30 μg/mL) and 8-hydroxyquinoline (2.12 and 5.28 μg/mL). Moreover, compound displayed excellent antifungal activity, which was comparable in activity to the commercial fungicide boscalid. The preliminary mechanism revealed that compound might cause an abnormal morphology of cell membranes, an increase in membrane permeability, and release of cellular contents. These results indicated that compound displayed superior and fungicidal activities and could be a potential fungicidal candidate against plant fungal diseases.
受我们之前简化奎宁结构和利用天然产物对抗植物病原真菌的创新应用的启发，选择先导化合物 2,8-双（三氟甲基）-4-喹啉醇（）作为候选物，并对其进行了多样化设计、合成和抗真菌评估。所有合成的化合物都针对四种重要的农业真菌、、、和进行了抗真菌活性评估。结果表明，化合物、、、、、、、、、和表现出良好的抗真菌效果，尤其是化合物具有最强的活性，对和的 EC 值分别为 0.52 和 0.50 μg/mL，优于先导化合物（1.72 和 1.89 μg/mL）和商业杀菌剂肟菌酯（均 >30 μg/mL）和 8-羟基喹啉（2.12 和 5.28 μg/mL）。此外，化合物对显示出优异的抗真菌活性，与商业杀菌剂烯酰吗啉相当。初步的机制表明，化合物可能导致细胞膜形态异常、膜通透性增加和细胞内容物释放。这些结果表明，化合物对和具有优异的杀菌活性，可能是防治植物真菌病害的潜在杀菌剂候选物。
