N-[p-(取代氨基磺酰基)苯基]-α-龙脑烯酸酰胺化合物的合成及其抑菌活性

Synthesis and Antifungal Activity of N-[p-(Substituted Sulfamoyl)Phenyl]-α-Campholenamide Compounds

以α-蒎烯为原料,经环氧化和催化异构得到α-龙脑烯醛,再经氧化反应得到α-龙脑烯酸,进一步反应制得α-龙脑烯酸酰氯,然后与磺胺类化合物发生N-酰化反应,以32.8%~78.1%的收率合成了8个N-[4-(N-取代氨磺酰基)苯基]-α-龙脑烯酸酰胺化合物Ⅵ(a^h)。采用FTIR、1HNMR、13CNMR和ESI-MS对目标产物进行了结构表征。抑菌活性测试结果表明:在质量浓度50μg/m L下,目标化合物均显示了一定的抑菌活性,其中,化合物N-[p-(噻唑-2-基)氨基磺酰基苯基]-α-龙脑烯酸酰胺(Ⅵe)对小麦赤霉病菌和黄瓜枯萎病菌的抑制率分别为71.3%和68.0%。

α-Campholenic aldehyde was prepared by epoxidation and catalytic isomerization reactions using α-pinene as starting materials,then it was oxidized to give α-campholenic acid,which was further converted into acyl chloride. Eight novel α-campholenic aldehyde-based amide-sulfonamide compoundsⅥ（a ~ h） were synthesized with the yeild of 32. 8% - 78. 1% by N-acylation reaction of the acylghloride with various sulfonamides. All the target compounds were characterized by FTIR,1HNMR,13 CNMR and ESI-MS. Antifungal activity tests showed that all the target compounds exhibited a certain antifungal activity at the concentration of 50 μg/m L. Compound N-[p-（thiazol-2-yl） aminosulfonyl]phenyl-α-campholenamide（Ⅵ e） had an inhibition ratio of 71. 3% and 68. 0%against Fusarium graminearum and Fusarium oxysporum f. cucumerinum,respectively.