Laboratory of Pesticidal Design & Synthesis, Department of Plant Protection, College of Horticulture and Plant Protection, Henan University of Science and Technology, Luoyang, 471023, P. R. China.
College of Plant Protection, Henan Agricultural University, Zhengzhou, 450002, China.
Chem Biodivers. 2023 Jul;20(7):e202300607. doi: 10.1002/cbdv.202300607. Epub 2023 Jun 21.
Using cinchona alkaloid as the lead compound, twenty-four cinchona alkaloid sulfonate derivatives (1 a-l, 2 a-c, 3 a-c, 4 a-c, and 5 a-c) were designed and prepared by modifying their C9 position, and structurally confirmed by H-NMR, C-NMR, HR-MS and melting points. Moreover, the stereochemical configurations of compounds 1 f and 1 l were unambiguously confirmed by single-crystal X-ray diffraction. Furthermore, we determined the anti-oomycete and anti-fungal activities of these target compounds against Phytophthora capsici and Fusarium graminearum in vitro. The results showed that two compounds 4 b and 4 c exhibited prominent anti-oomycete activity, and the median effective concentration (EC ) values of 4 b and 4 c against P. capsici were 22.55 and 16.32 mg/L, respectively. This study suggested that when the C9 position of cinchona alkaloid sulfonate derivatives is in the S configuration and the 6'-position methoxy group is not present, the anti-oomycete activity is superior. In addition, five compounds 1 e, 1 f, 1 k, 3 c and 4 c displayed significant anti-fungal activity, with EC values of 43.64, 45.07, 80.18, 48.58 and 41.88 mg/L against F. graminearum, respectively. This result indicates that only when a specific substituent is introduced into the structural framework of the target compound, the corresponding compound exhibits significant inhibitory activity against fungi.
以金鸡纳生物碱为先导化合物，通过修饰其 C9 位，设计并合成了 24 个金鸡纳生物碱磺酸盐衍生物（1a-l、2a-c、3a-c、4a-c 和 5a-c），通过 1H-NMR、13C-NMR、HR-MS 和熔点等方法对其结构进行了确证。此外，通过单晶 X 射线衍射实验，明确了化合物 1f 和 1l 的立体化学构型。进一步测定了目标化合物对辣椒疫霉和禾谷镰刀菌的抗真菌和抗卵菌活性。结果表明，两个化合物 4b 和 4c 表现出显著的抗卵菌活性，化合物 4b 和 4c 对辣椒疫霉的半数有效浓度（EC50）分别为 22.55 和 16.32mg/L。研究表明，当金鸡纳生物碱磺酸盐衍生物 C9 位为 S 构型且 6′-位无甲氧基取代时，抗卵菌活性较强。此外，化合物 1e、1f、1k、3c 和 4c 对禾谷镰刀菌具有显著的抗真菌活性，其 EC50 值分别为 43.64、45.07、80.18、48.58 和 41.88mg/L。这一结果表明，只有当特定的取代基被引入目标化合物的结构框架中时，相应的化合物才会对真菌表现出显著的抑制活性。
