具色素抑制作用的酰胺基香豆素的合成、构-效关系及作用机理研究

项目名称： 具色素抑制作用的酰胺基香豆素的合成、构-效关系及作用机理研究

项目编号： No.31471808

项目类型： 面上项目

立项/批准年度： 2015

项目学科： 农业科学

项目作者： 郝双红

作者单位： 青岛农业大学

项目金额： 85万元

中文摘要： 天然香豆素广泛存在于自然界，种类丰富，活性多样，是一类经典化感作用物质。酰胺类除草剂中吡氟酰草胺等与传统氯代乙酰胺类作用机理不同，为类胡萝卜素生物合成抑制剂，目前在应用中受到广泛关注。项目前期基于活性亚结构拼接思想，设计合成了一类酰氨基香豆素，筛选发现新化合物N-乙酰基及N-苯甲酰基取代的N-（间-氟-苯基甲基）-6-氨基香豆素（Ⅲe1及Ⅲe2）具显著除草活性，可导致马唐幼苗白化，作用不同于香豆素，与吡氟酰草胺类似，可显著降低马唐叶中类胡萝卜素及叶绿素含量。该课题拟在此基础上，进一步利用类同合成法用不同酰基对N-（间-氟-苯基甲基）-6-氨基香豆素（Ⅲe）上的氨基进行酰化衍生，并对其白化除草活性进行评价，建立构-效QSAR模型；依此推测高活性化合物结构，建立自主产权活性分子模板，以期发现具开发价值的新化合物；同时对该类化合物的白化除草作用靶标进行初步探索，为其研究开发奠定基础。

中文关键词： 酰胺基香豆素；合成；构-效关系；作用机理；色素抑制

英文摘要： Coumarin is a kind of widely dispersed naturally occurred compounds, which are rich variety, diverse bioactivity and especially strong allelopathy. Amide herbicide Diflufenican with action mechanism of inhibiting the biosynthesis of carotenoid which are different with the conventional herbicide chloro-acetamide received extensive attention nowady. A class of N-acyl (or alkyl) amino coumarins were designed and synthesized based on substructure combination in this project preparation by us. Bioassay screening revealed that new compounds N-acetyl-N-(m-fluoro-phenyl-methyl)-6-amino coumarin (Ⅲe1) and N-benzoyl-N-(m- fluoro-phenyl-methyl)-6-amino coumarin(Ⅲe2) were high herbicidal, which could inhibit the seedling of Digitaria sanguinalis become green. The action mode of the 2 herbicidal compounds (Ⅲe1 and Ⅲe2) who remarkably reduced the carotenoid and chlorophyll content of the leaf of exposed Digitaria sanguinalis was different with coumarin, while similar with Amide herbicide Diflufenican. Based on these knowledge, we plan to design and synthesize a class of compounds with different acyl group on N atom of N-(m-fluoro-phenyl-methyl)-6-amino coumarin, and the bleaching herbicidal activity of the target compounds will be evaluated. After that the quality structure-activity relationship (QSAR) of them will be built. Then the ideal potential compound structure may be predicted, and the self-property right active molecular template will be set up, the commercial herbicide candidate could be screened out as well. We also would like to study the bleaching mechanism of these compounds. The research would produce necessary information for study and development of this new kind compound.

英文关键词： Amide Coumarin;Synthesis;Structure-Activity Relationship;Action Mechanism;Pigment Inhibition