N-(4-(N-取代氨磺酰基)苯基)-α-龙脑烯酸酰胺化合物
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TQ351

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国家自然科学基金项目(31260164);广西高校科学技术研究重点项目(ZD2014098)


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

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马献力,黄铎云,段文贵,林桂汕,陈智聪. N-(4-(N-取代氨磺酰基)苯基)-α-龙脑烯酸酰胺化合物[J].精细化工,2016,33(10):

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  • 收稿日期:2016-03-08
  • 最后修改日期:2016-05-27
  • 录用日期:2016-07-04
  • 在线发布日期: 2016-09-13
  • 出版日期: