吲哚衍生物的合成及其海洋防污性能

以吲哚和酰氯(苯甲酰氯及苯磺酰氯)为原料,合成了7个N-酰基取代吲哚类化合物(a^g),其结构经1H NMR和元素分析确证。研究了化合物对球等鞭金藻、亚心形扁藻和舟形藻以及藤壶幼虫的生长抑制活性。结果表明:当吲哚结构连接电负性较高的基团时,化合物对藻类和藤壶幼虫的生长抑制性较好,其中以连接苯磺酰基化合物的抑制效果最佳。目标化合物对藤壶幼虫12 h和24 h的半致死浓度(LC50)明显低于底物吲哚,其中以苯磺酰基取代的化合物最低。采用目标化合物制备的海洋防污涂料,浅海挂板90 d后,对海洋污损生物的附着表现出明显的抑制作用。

Synthesis and Antifouling Properties of Indole Derivatives

Seven N-acyl substituted indole compounds(a^g)were synthesized through the indole and acyl chloride(benzoyl chloride or benzene sulfochloride)as raw material.The structure were confirmed by 1H NMR and elemental analysis.The inhibitory activities of the target compounds against Isochrysisgalbana,Platymonassubcordiformis,Navicula and Barnacle larvae were tested.The results showed that the growth inhibition of algae and barnacle larvae was better than the precursor when the electronegative groups connected to N-position of indole ring.Among them,the inhibition effect of N-sulfonyl substituted compounds is the best.The half lethal concentration(LC50)of the target compounds for barnacle larvae at 12 h and 24 h was significantly lower than substrate indole.It is noteworthy that the LC50 of the target compounds substituted by sulfonyl group is lower.Consequently,the marine antifouling coating prepared by the target compound showed obvious inhibition on the adhesion of marine fouling organisms after 90 d of marine field test.