3-D-QSAR CoMFA and CoMSIA studies on tetrahydrofuroyl-L-phenylalanine derivatives as VLA-4 antagonists

Bioorg Med Chem. 2003 Sep 15;11(19):4235-44. doi: 10.1016/s0968-0896(03)00408-5.

Abstract

Comparative molecular field analysis (CoMFA) and comparative molecular similarity indices analysis (CoMSIA) were performed on tetrahydrofuroyl-L-phenylalanine derivatives as VLA-4 antagonists. The best CoMFA and CoMSIA models that were generated using atom based alignment from a training set of twenty five tetrahydrofuroyl-L-phenylalanine derivatives, are six-component models with good statistics; CoMFA: r(2)(cv)=0.366, r(2)=0.983, s=0.099, F=172.661 and PRESS=4.435; CoMSIA: r(2)(cv)=0.528, r(2)=0.995, s=0.054, F=577.87 and PRESS=3.563. Both of these 3-D-QSAR models were validated using a test set of eleven compounds, whose predicted pIC(50) values fall within one log unit of the actual pIC(50). The contour diagrams obtained for the various CoMFA and CoMSIA field contributions can be mapped back onto structural features to explain the activity trends of the molecules analysed. Based on the spatial arrangement of the various field contributions, novel molecules with improved activity can be designed.

Publication types

  • Comparative Study

MeSH terms

  • Binding Sites
  • Computer Simulation
  • Enzyme Inhibitors / chemistry*
  • Enzyme Inhibitors / pharmacology
  • Furans / chemistry*
  • Furans / pharmacology
  • Hydrogen Bonding
  • Inhibitory Concentration 50
  • Integrin alpha4beta1 / antagonists & inhibitors*
  • Molecular Conformation
  • Phenylalanine / analogs & derivatives*
  • Phenylalanine / pharmacology
  • Quantitative Structure-Activity Relationship
  • Static Electricity
  • Stereoisomerism

Substances

  • Enzyme Inhibitors
  • Furans
  • Integrin alpha4beta1
  • Phenylalanine