López Génesis, Mellado Marco, Werner Enrique, Said Bastián, Godoy Patricio, Caro Nelson, Besoain Ximena, Montenegro Iván, Madrid Alejandro
Laboratorio de Productos Naturales y Síntesis Orgánica (LPNSO), Departamento de Química, Facultad de Ciencias Naturales y Exactas, Universidad de Playa Ancha, Avda. Leopoldo Carvallo 270, Playa Ancha, Valparaíso 2340000, Chile.
Instituto de Química, Facultad de Ciencias, Pontificia Universidad Católica de Valparaíso, Av. Universidad #330, Curauma, Valparaíso 2340000, Chile.
Antibiotics (Basel). 2020 Sep 4;9(9):576. doi: 10.3390/antibiotics9090576.
This work reports on the synthesis of eight new 2'-hydroxy-chalcones with potential anti-phytopathogenic applications in agroindustry, among others, via Claisen-Schmidt condensation and ultrasound assisted reaction. Assays showed three chalcones with allyl moieties strongly inhibited growth of phytopathogenic oomycete ; moreover, compound had a half maximal effective concentration (EC) value (32.5 µg/mL) similar to that of metalaxyl (28.6 µg/mL). A software-aided quantitative structure-activity relationship (QSAR) analysis of the whole series suggests that the structural features of these new chalcones-namely, the fluoride, hydroxyl, and amine groups over the carbon 3' of the chalcone skeleton-increase anti-oomycete activity.
本研究报道了通过克莱森-施密特缩合反应和超声辅助反应合成了八种新型2'-羟基查耳酮,这些查耳酮在农业工业等领域具有潜在的抗植物病原菌应用。试验表明,三种含有烯丙基部分的查耳酮强烈抑制植物病原卵菌的生长;此外,化合物的半数有效浓度(EC)值(32.5μg/mL)与甲霜灵(28.6μg/mL)相似。对整个系列进行的软件辅助定量构效关系(QSAR)分析表明,这些新型查耳酮的结构特征,即查耳酮骨架3'位碳上的氟、羟基和胺基,增强了抗卵菌活性。