N-(4-(N-取代氨磺酰基)苯基)-α-龙脑烯酸酰胺化合物

Synthesis and Antifungal Activity of N-(4-(N-Substituted Sulfamoyl) Phenyl)-α-Campholenamide Compounds

摘要:

为了寻找天然产物基抑菌剂，以α-蒎烯(I)为原料，经环氧化和催化异构得到α-龙脑烯醛(III)，进一步转化为α-龙脑烯酸(IV)和α-龙脑烯酸酰氯(V)，然后与4-(N-取代氨磺酰基)苯胺类化合物发生N-酰化反应，以32.8~78.1%的收率合成得到8个N-(4-(N-取代氨磺酰基)苯基)-α-龙脑烯酸酰胺化合物VIa～VIh。采用FTIR、1HNMR、13CNMR和ESI-MS对目标产物进行结构表征。抑菌活性测试表明，在50 µg/mL质量浓度下，目标化合物显示一定的抑菌活性，其中化合物N-[4-(N-(噻唑-2-基)氨磺酰基)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%（活性级别为B级）和68.0%（活性级别为C级）。

Abstract:

In an attempt to search for natural product-based antifungal agents, α-campholenic aldehyde (III) was prepared by epoxidation and catalytic isomerization of α-pinene (I), and then converted into -campholenic (IV) acid and its acylchloride (V). Eight novel N-(4-(N-substituted sulfamoyl) phenyl)-α-campholenamide Ⅵa～Ⅵh were synthesized by N-acylation reaction of the acylchloride with various 4-amino-N-substituted benzenesulfonamide in 32.8~78.1% yield. All the target compounds were characterized by FTIR, 1HNMR, 13CNMR and ESI-MS. Antifungal activity test showed that, at the concentration of 50 µg/mL, all the target compounds exhibited a certain antifungal activity, in which compound N-[4-(N-(thiazol-2-yl)sulfamoyl)phenyl]-α-campholenamide(VIe) had inhibition ratio of 71.3% (B-class activity level) and 68.0% (C-class activity level) against Fusarium graminearum and Fusarium oxysporum f. cucumerinum, respectively.