含肟酯/醚结构的枯茗醛衍生物合成及抑菌活性

Synthesis and antibacterial activity of cuminaldehyde derivatives containing oxime ester/ether fragments

以孜然精油的主要成分枯茗醛为原料,设计合成了系列含肟酯/醚结构的枯茗醛衍生物18个,并通过^(1)H NMR、^(13)C NMR和HRMS进行了结构表征;以地毯草黄单胞柑橘致病变种和水稻黄单胞菌为对象,采用浑浊度法对目标化合物的抑菌活性进行了评估。抑菌活性测试结果表明:化合物(Z)-4-异丙基苯甲醛-O-(3-甲氧基苯甲酰基)肟(4i)在质量浓度50μg·mL^(-1)下对地毯草黄单胞柑橘致病变种的抑制率为3280%,优于对照药剂叶枯唑(1688%);目标化合物(Z)-4-异丙基苯甲醛-O-(苯甲酰基)肟(4d)、(Z)-4-异丙基苯甲醛-O-(4-三氟甲基苯甲酰基)肟(4h)和(Z)-4-异丙基苯甲醛-O-(3-甲氧基苯甲酰基)肟(4i)在质量浓度100μg·mL-1下对地毯草黄单胞柑橘致病变种的抑制率分别为60.3%、31.37%和33.30%,优于对照药剂叶枯唑的抑制率(45.82%)。

A series of 18 cuminal derivatives containing oxime ester/ether structure fragments were designed and synthesized by u-sing the main component of cumin essential oil cuminaldehyde as material,and their structures were characterized by^(1)H NMR,^(13)C NMR and HRMS.The antibacterial activity of the target compounds against Xanthomonas axonopodis pv.citri and Xanthomonas oryzae pv.oryzae were evaluated by the turbidity method.The inhibitory activity results declared that(E)-4-isopropylbenzaldehyde-O-(3-methoxybenzyl)oxime(4i)had an inhibitory activity of 32.80%toward Xanthomonas axonopodis pv.citri at 50μg·mL^(-1),which was higher than that of the control agent bismerthiazol(16.88%);(E)-4-isopropylbenzaldehyde-O-benzyl oxime(4d),(E)-4-isopropylbenzaldehyde-O-(4-(trifluoromethyl)benzyl)oxime(4h),(E)-4-isopropylbenzaldehyde-O-(3-methoxybenzyl)oxime(4i)had an inhibitory activity of 60.3%,31.37%and 33.30%toward Xanthomonas axonopodis pv.citri at 100μg·mL^(-1),respec-tively,which was higher than that of the control agent bismerthiazol(45.82%).