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

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

doi:10.1007/BF00141575

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

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

Research output: Contribution to journal › Article › Research › peer-review

24 Citations (Scopus)

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 language	English
Pages (from-to)	61-69
Number of pages	9
Journal	Journal of Computer-Aided Molecular Design
Volume	7
Issue number	1
DOIs	https://doi.org/10.1007/BF00141575
Publication status	Published - 1 Feb 1993
Externally published	Yes

Keywords

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

Access to Document

10.1007/BF00141575

Link to publication in Scopus

Cite this

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title = "Chiral chromatography and multivariate quantitative structure-property relationships of benzimidazole sulphoxides",

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.",

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year = "1993",

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AU - Manallack, David T.

PY - 1993/2/1

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AB - 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.

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