Chiral chromatography and multivariate quantitative structure-property relationships of benzimidazole sulphoxides.
Various benzimidazole sulphoxides were chirally resolved employing an amylase-based chiral stationary phase. The structure-property relationships of these compounds were investigated using calculated physicochemical 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.
Camilleri
P
P
SmithKline Beecham Pharmaceuticals, The Frythe, Welwyn, Herts, U.K.
Livingstone
D J
DJ
Murphy
J A
JA
Manallack
D T
DT
D000897:Anti-Ulcer Agents / Q000737:chemistry / Q000302:isolation & purification; D001562:Benzimidazoles / Q000737:chemistry* / Q000302:isolation & purification; D002851:Chromatography, High Pressure Liquid; D004563:Electrochemistry; D015394:Molecular Structure; D015999:Multivariate Analysis; D012984:Software; D013237:Stereoisomerism
D000897:Anti-Ulcer Agents; D001562:Benzimidazoles