新型含吲哚环酯类化合物的合成、抑藻活性及构效关系研究

Synthesis and QSAR Studies on Anti-algae Activities of Novel Ester Derivatives Containing Indole Ring

从苔藓虫Zoobotryon pellucidum中提取的2,5,6-三溴-1-甲基芦竹碱(TBG)能较好地抑制海洋生物藤壶的附着.为提高该类化合物在防污涂料中的复配性能,合成了4个新型的不同卤素取代和N-取代且具有较好亲脂性能的TBG类似物.通过1H NMR,13C NMR,IR和元素分析对目标化合物6a～6d进行了结构表征.生物实验结果表明,化合物5～6对海藻Nitzschia closterium均具有较好的生长抑制活性,其中以亲脂性较强的6b和6d抑制作用最为显著,LC50分别可达1.33μg/mL和1.06μg/mL.对化合物的定量构效关系进行了初步探讨.

2,5,6-Tribromo-1-methylgramine （TBG）, isolated from the bryozoan Zoobotryon pellucidum was shown to be very efficient in preventing recruitment of larval settlement. In order to improve the compatibility of these compounds with other ingredients in antifouling paints, structural modification of TBG was focused most on halogen substitution and N-substitution. Four novel TBG analogues with higher lipophilic activity were synthesized. The structures of 6a-6d were established by ^1H NMR, ^13C NMR, IR spectra and elemental analysis. The bioassay results showed that all compounds （5-6） possessed good anti-algae activities, and the LC50 value against Nitzschia closterium showed that 6b and 6d exhibited higher activities （6b： LC50= 1.33 μg/mL, 6d： LC50= 1.06 μg/mL） than others. The primary quantitative structure activity relationship was discussed.