螺靛红呋喃衍生物的合成及活性研究

Synthesis and antifungal activities of spiro [furan-3,3'-indoline] derivatives

为了合成同时具有呋喃和靛红骨架的化合物,通过三乙胺催化羟醛缩合/环化/质子迁移串联反应,提供了一种高效、温和及方便合成螺靛红呋喃衍生物的方法.在优化的条件下,以中等到良好的收率获得了一系列螺靛红呋喃衍生物.同时,对该类化合物进行了抑菌活性的初步研究,结果表明:5-氨基-2-[(E)-4-氯苯乙烯基]-2-氧代-螺靛红呋喃4ac能很好地抑制供试菌番茄早疫病菌菌丝生长,而5-氨基-2-[(E)-4-三氟甲基苯乙烯基]-2-氧代-螺靛红呋喃4ag也能强烈抑制供试菌小麦赤霉病菌菌丝生长,它们的抑制率分别为65.0%,85.9%.

In order to synthesize compounds which contained both furan and 2-oxoindole units,an efficient,mild,and convenient method for preparation of spirooxindole furan derivatives via a domino Aldol/cyclization/proton shift reaction catalyzed by triethylamine was developed. A series of spirooxindole furan derivatives were obtained with moderate to good yields when the domino reactions were carried out in the optimized conditions.In addition,preliminary antifungal activities of all compounds were investigated. The results indicated that5-amino-2-((E)-4-chlorostyryl)-2'-oxo-2 H-spiro[furan-3,3'-indoline]-4-carbonitrile 4 ac displayed higher antifungal activity against Alternaria solani and 5-amino-2'-oxo-2-((E)-4-(trifluoromethyl) styryl)-2 H-spiro[furan-3,3'-indoline]-4-carbonitrile 4 ag also exhibited strong antifungal properties with relatively higher selectivity against Fusarium graminearum with inhibition rate of 65. 0%,85. 9%,respectively.