Synthesis, antifeedant activity against Coleoptera and 3D QSAR study of alpha-asarone derivatives

SAR QSAR Environ Res. 2014;25(3):173-88. doi: 10.1080/1062936X.2013.875061. Epub 2014 Mar 7.

Abstract

For the first time, a set of 56 compounds representing structural derivatives of naturally occurring alpha-asarone as an antifeedants against stored product pests Sitophilus granarius L., Trogoderma granarium Ev., and Tribolium confusum Duv., were subjected to the 3D QSAR studies. Three-dimensional quantitative structure-activity relationships (3D-QSAR) for 56 compounds, including 15 newly synthesized, were performed using comparative molecular field analysis s-CoMFA and SOM-CoMSA techniques. QSAR was conducted based on a combination of biological activity (against Coleoptera larvae and beetles) and various geometrical, topological, quantum-mechanical, electronic, and chromatographic descriptors. The CoMSA formalism coupled with IVE (CoMSA-IVE) allowed us to obtain highly predictive models for Trogoderma granarium Ev. larvae. We have found that this novel method indicates a clear molecular basis for activity and lipophilicity. This investigation will facilitate optimization of the design of new potential antifeedants.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Allylbenzene Derivatives
  • Animals
  • Anisoles / chemical synthesis*
  • Anisoles / pharmacology*
  • Coleoptera / drug effects*
  • Insect Repellents / chemical synthesis*
  • Insect Repellents / pharmacology*
  • Quantitative Structure-Activity Relationship*

Substances

  • Allylbenzene Derivatives
  • Anisoles
  • Insect Repellents
  • asarone