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

Xia Li; Liangmin Yu; Xiaohui Jiang; Shuwei Xia; Haizhou Zhao

doi:10.1007/s00343-009-9212-1

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

OriginalPaper | Updated：2023-05-16

- Synthesis, algal inhibition activities and QSAR studies of novel gramine compounds containing ester functional groups
- Synthesis, algal inhibition activities and QSAR studies of novel gramine compounds containing ester functional groups
- 海洋湖沼学报（英文） 2009年27卷第2期页码：309-316
- Affiliations：
  
  Education Ministry Key Laboratory of Marine Chemistry Theory and Technology Ocean University of China
- Author bio：
- Funds：
  
  Supported by the National Natural Science Foundation of China (No. 50673085, 20060423017, A1420080191);National High-Technology Research Program of China (863 Program, No. 2006AA09Z224)
- DOI：10.1007/s00343-009-9212-1
  中图分类号：
- 网络首发：2009-07-12，
  
  纸质出版：2009
- Accepted：
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Synthesis, algal inhibition activities and QSAR studies of novel gramine compounds containing ester functional groups[J]. 海洋湖沼学报（英文）, 2009,27(2):309-316.

Li, X., Yu, L., Jiang, X. et al. Synthesis, algal inhibition activities and QSAR studies of novel gramine compounds containing ester functional groups., Chin. J. Ocean. Limnol. 27, 309–316 (2009). https://doi.org/10.1007/s00343-009-9212-1
Synthesis, algal inhibition activities and QSAR studies of novel gramine compounds containing ester functional groups[J]. 海洋湖沼学报（英文）, 2009,27(2):309-316. DOI： 10.1007/s00343-009-9212-1.

Li, X., Yu, L., Jiang, X. et al. Synthesis, algal inhibition activities and QSAR studies of novel gramine compounds containing ester functional groups., Chin. J. Ocean. Limnol. 27, 309–316 (2009). https://doi.org/10.1007/s00343-009-9212-1 DOI：

摘要

Abstract

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.

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references

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