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

Updated：2023-05-16

- Synthesis, algal inhibition activities and QSAR studies of novel gramine compounds containing ester functional groups
- Journal of Oceanology and Limnology Vol. 27, Issue 2, Pages: 309-316(2009)
- Affiliations：
  
  Education Ministry Key Laboratory of Marine Chemistry Theory and Technology Ocean University of China
- Author bio：
- Funds：
- DOI：10.1007/s00343-009-9212-1
  CLC：
- Online First：12 July 2009，
  
  Published：2009
- Accepted：
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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：

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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