新型去氢枞酸基磺酰胺类化合物的合成及其生物活性  

Synthesis and Biological Activities of Novel Dehydroabietic Acid-based Sulfamide Compounds

作　　者：闵方倩 段文贵[1] 林桂汕[1] 石贤春 谭洪兵 杨章旗[2] 

机构地区：[1]广西大学化学化工学院,广西南宁530004 [2]广西林业科学研究院,广西南宁530002

出　　处：《合成化学》2014年第3期281-287,共7页Chinese Journal of Synthetic Chemistry

基　　金：国家自然科学基金资助项目(31060100);广西自然科学基金重点资助项目(2010GXNSFD013013);八桂学者专项资助项目(松树资源培育及产业化关键技术创新)

摘　　要：去氢枞酸与SOCl2反应制得去氢枞酸酰氯(2);芳磺酰氯与乙二胺经N-酰化反应制得N-芳磺酰基乙二胺(4a^4k);在DMAP催化下,2分别与4a^4k经N-酰化反应合成了11个新型的去氢枞酸基磺酰胺类化合物(5a^5k),其结构经1H NMR,13C NMR,IR和ESI-MS表征。生物活性测试结果表明,在用药量为50μg·mL-1时,5a^5k对黄瓜枯萎病菌、苹果轮纹病菌、番茄早疫病菌、花生褐斑病菌和小麦赤霉病菌有一定的抑菌活性,其中去氢枞酸基间甲基苯磺酰胺(5c)对番茄早疫病菌的杀菌活性最佳,抑制率为73.6%;在用药量为100μg·mL-1时,大部分化合物对油菜的胚根生长有一定抑制作用,其中去氢枞酸基对甲氧基苯磺酰胺(5d)的抑菌活性最佳,抑菌率为57.1%。Dehydroabietic acid acyl chloride （2） was prepared by the reaction of dehydroabietic acid with thionyl chloride.N-aryl sulfonyl ethylenediamines（4a ～ 4k） was prepared by the N-acylation of aryl sulfonyl chloride with ethylenediamine.Eleven novel dehydroabietic acid-based sulfonamide compounds（5a ～ 5k） were synthesized by N-acylation reaction of 2 with 4a ～ 4k,respectively,using DMAP as the catalyst.The structures were characterized by 1H NMR,13C NMR,IR and ESIMS.The preliminary bioassay showed that 5a ～ 5k exhibited certain fungicidal activities against Fusarium oxysporum f.sp.cucumerinum,Physalospora piricola,Alternaria solani,Cercospora Rachidicola and Fusarium graminearum.Inhibition rate against Alternaria solani of dehydroabietic acid-based mmethyl-benzenesulfonamide（5c） was 73.6% at 50μg · mL-1.Most of 5a ～ 5k exhibited certain growth inhibition activities against rape root （Brassica campestris）,inhibition rate of dehydroabietic acid-based p-methoxyl-benzenesulfonamide（5d） was 57.1% at 100μg · mL-1.

关 键 词：去氢枞酸 磺酰胺 合成 杀菌活性 除草活性 

分 类 号：O621.3[理学—有机化学]