Chiral chromatography and multivariate quantitative structure-property relationships of benzimidazole sulphoxides

Patrick Camilleri, David J. Livingstone, José A. Murphy, David T. Manallack

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Abstract

Various benzimidazole sulphoxides were chirally resolved employing an amylase-based chiral stationary phase. The structure-property relationships of these compounds were investigated using calculated physico-chemical properties, molecular modelling and multivariate statistical techniques. A data set of 254 molecular descriptors was used to represent the series of compounds. Analysis of the data set using principal components analysis and non-linear mapping suggested that the separation factor of each enantiomeric pair was associated with nine molecular properties and, in particular, molar refractivity of the Z substituent and the partial charge of atom 6. The separation factor of a sulphoxide not used in the analysis was well predicted thus suggesting that these models may be used to generalize.

Original languageEnglish
Pages (from-to)61-69
Number of pages9
JournalJournal of Computer-Aided Molecular Design
Volume7
Issue number1
DOIs
Publication statusPublished - 1 Feb 1993
Externally publishedYes

Keywords

  • Computational chemistry
  • Non-linear mapping
  • Pattern recognition
  • Principal components analysis
  • Unsupervised learning

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