6-苄氧基吲哚-2-甲酸糠醇酯衍生物的合成及其抗稻瘟霉菌活性  

Synthesis and Pyricularia oryzae inhibitory activities of furfuryl 6-benzyloxy-1H-indole-2-carboxylate derivatives

作　　者：李林[1] 赵玲玲[1] 董肖椿[1] 郑剑斌[1] 闻韧[1] 

机构地区：[1]复旦大学药学院,上海200032

出　　处：《中国药物化学杂志》2007年第3期129-134,共6页Chinese Journal of Medicinal Chemistry

基　　金：上海市科委重大攻关项目(03DZ19201)

摘　　要：目的设计合成一系列6-苄氧基吲哚-2-甲酸糠醇酯衍生物,并测试其抗稻瘟霉菌活性。方法以4-羟基苯甲醛为原料,经O-苄基化、Knoevenagel反应、重排和水解反应得到6-苄氧基吲哚-2-甲酸(6),6与5-氯甲基糠醛反应得到6-苄氧基吲哚-2-甲酸-(5-甲酰基糠醇)酯(1),1分别经过还原、还原胺化和Knoevenagel反应得到相应的目标化合物。体外活性采用稻瘟霉菌筛选模型进行评价。结果与结论合成了13个新化合物,其结构经核磁共振氢谱、质谱确证,其中化合物1、8e、8f、8g的活性优于阳性对照灰黄霉素(griseofulvin)。Aim To design and synthesize furfuryl 6-benzyloxy-1H-indole-2-carboxylate derivatives and to evaluate their Pyricularia oryzae inhibitory activities. Methods Starting from 4-hydroxybenzaldehyde, after O-benzylation, Knoevenagel condensation, rearrangement, and hydrolysis, 6-benzyloxy-1H-indole-2-carboxylic acid （6） was obtained, which then was reacted with 5-chloromethylfurfuraldehyde to give 5-formylfurfuryl 6-benzyloxy-1H-indole-2-carboxylate（1）. 1 was subsequently converted to the target compounds via reduction, reductive amination, and Knoevenagel condensation respectively. The in vitro biological activities were evaluated with conidia of Pyricularia oryzae. Results and conclusion Thirteen new target compounds were synthesized with structures confirmed by ^1H-NMR and MS. The Pyricularia oryzae inhibitory activities of compounds 1,8e, 8f, and 8g were more potent than that of griseofulvin.

关 键 词：4-羟基苯甲醛 6-苄氧基吲哚-2-甲酸糠醇酯衍生物 稻瘟霉菌抑制活性 

分 类 号：R914.5[医药卫生—药物化学]