Synthesis,algal inhibition activities and QSAR studies of novel gramine compounds containing ester functional groups  

作　　者：李霞 于良民 姜晓辉 夏树伟 赵海洲 

机构地区：[1]Education Ministry Key Laboratory of Marine Chemistry Theory and Technology,Ocean University of China

出　　处：《Chinese Journal of Oceanology and Limnology》2009年第2期309-316,共8页中国海洋湖沼学报（英文版）

基　　金：Supported by the National Natural Science Foundation of China (No. 50673085, 20060423017, A1420080191);National High-Technology Research Program of China (863 Program, No. 2006AA09Z224)

摘　　要：2,5,6-Tribromo-l-methylgramine （TBG）, isolated from bryozoan Zoobotryon pellucidum was shown to be very efficient in preventing recruitment of larval settlement. In order to improve the compatibility of TBG and its analogues with other ingredients in antifouling paints, structural modification of TBG was focused mainly on halogen substitution and N-substitution. Two halogen-substitute gramines and their derivatives which contain ester functional groups at N-position of gramines were synthesized. Algal inhibition activities of the synthesized compounds against algae Nitzschia cIosterium were evaluated and the Median Effective Concentration （EC50） range was 1.06-6.74 lag ml^-1. Compounds that had a long chain ester group exhibited extremely high antifouling activity. Quantitive Structure Activity Relationship （QSAR） studies with multiple linear regression analysis were applied to fred correlation between different calculated molecular descriptors and biological activity of the synthesized compounds. The results show that the toxicity （log （I/EC50）） is correlated well with the partition coefficient log P. Thus, these products have potential function as antifouling agents.2,5,6-Tribromo-1-methylgramine (TBG), isolated from bryozoan Zoobotryon pellucidum was shown to be very efficient in preventing recruitment of larval settlement. In order to improve the compatibility of TBG and its analogues with other ingredients in antifouling paints, structural modification of TBG was focused mainly on halogen substitution and N-substitution. Two halogen-substitute gramines and their derivatives which contain ester functional groups at N-position of gramines were synthesized. Algal inhibition activities of the synthesized compounds against algae Nitzschia closterium were evaluated and the Median Effective Concentration (EC50) range was 1.06–6.74 μg ml-1. Compounds that had a long chain ester group exhibited extremely high antifouling activity. Quantitive Structure Activity Relationship (QSAR) studies with multiple linear regression analysis were applied to find correlation between different calculated molecular descriptors and biological activity of the synthesized compounds. The results show that the toxicity (log (1/EC50)) is correlated well with the partition coefficient log P. Thus, these products have potential function as antifouling agents.

关 键 词：gramine derivative SYNTHESIS algal inhibition activity QSAR 

分 类 号：X55[环境科学与工程—环境工程]