title: Synthesis, antifeedant activity against Coleoptera and 3D QSAR study of alpha-asarone derivatives.
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.
authors.affiliation: a Institute of Plant Protection - National Research Institute , Bialystok , Poland.
authors.forename: B
authors.initials: B
authors.lastname: Łozowicka
authors.forename: P
authors.initials: P
authors.lastname: Kaczyński
authors.forename: T
authors.initials: T
authors.lastname: Magdziarz
authors.forename: A T
authors.initials: AT
authors.lastname: Dubis
mesh_terms: D000081248:Allylbenzene Derivatives; D000818:Animals; D000840:Anisoles / Q000138:chemical synthesis* / Q000494:pharmacology*; D001517:Coleoptera / Q000187:drug effects*; D007302:Insect Repellents / Q000138:chemical synthesis* / Q000494:pharmacology*; D021281:Quantitative Structure-Activity Relationship
chemical_list: D000081248:Allylbenzene Derivatives; D000840:Anisoles; D007302:Insect Repellents; C012195:asarone