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Stereoselectivity in β‐cyclodextrin complexation of 1,4‐dihydropyridine derivatives
Author(s) -
FerčejTemeljotov Darja,
Kmet Matevž,
Kocjan Darko,
Kotnik Sonja,
Resman Aleksander,
Urleb Uroš,
Verhnjak Katarina,
Zver Igor,
Žmitek Janko
Publication year - 1993
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.530050419
Subject(s) - chemistry , enantiomer , solubility , stereoselectivity , differential scanning calorimetry , cyclodextrin , nuclear magnetic resonance spectroscopy , molecule , inclusion compound , organic chemistry , stereochemistry , physics , thermodynamics , catalysis
Structure–interaction relationships, stereoselectivity, and solubility enhancement in inclusion compexation of β‐cyclodextrins (CDs) with some racemic and enantiomerically pure 1,4‐dihydropyridine derivatives (DHPs) were investigated. 1:1 and 1:2 (mole ratio) complexes were prepared and characterized by X‐ray powder diffraction, differential scanning calorimetry (DSC), MS‐FAB spectrometry, 1 H‐NMR spectroscopy, water and phase solubility. The solubility studies have revealed different complexation equilibria for optically pure DHP enantiomers, and corresponding racemic mixtures in water solutions. By means of 1 H‐NMR chemical shift measurements, the inclusion of aromatic fragments of racemic and enantiomerically pure DHP molecules within the cavities of different CDs was elucidated. Considerable stereoselectivity in complexation interactions was observed. The results indicate the potential use of cyclodextrins as chiral selectors for enantiomeric resolution of 1,4‐DHP calcium antagonists. © 1993 Wiley‐Liss, Inc.