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Enantiomers of C 5 ‐chiral 1‐acetyl‐3,5‐diphenyl‐4,5‐dihydro‐(1 H )‐pyrazole derivatives: Analytical and semipreparative HPLC separation, chiroptical properties, absolute configuration, and inhibitory activity against monoamine oxidase
Author(s) -
Cirilli Roberto,
Ferretti Rosella,
Gallinella Bruno,
Turchetto Luciana,
Bolasco Adriana,
Secci Daniela,
Chimenti Paola,
Pierini Marco,
Fares Vincenzo,
Befani Olivia,
La Torre Francesco
Publication year - 2004
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.20085
Subject(s) - chemistry , enantiomer , absolute configuration , high performance liquid chromatography , chromatography , chiral column chromatography , pyrazole , stereochemistry
The HPLC enantiomer separation of a novel series of C 5 ‐chiral 1‐acetyl‐3‐(4‐hydroxy‐ and 2,4‐dihydroxyphenyl)‐5‐phenyl‐4,5‐dihydro‐(1 H )‐pyrazole derivatives, with inhibitory activity against monoamine oxidases (MAO) type A and B, was accomplished using polysaccharide‐based chiral stationary phases (CSPs: Chiralpak AD, Chiralcel OD, and Chiralcel OJ). Pure alcohols, such as ethanol and 2‐propanol, and typical normal‐phase binary mixtures, such as n ‐hexane and alcohol modifier, were used as mobile phases. Single enantiomers of several analytes examinated were isolated on a semipreparative scale, and their chiroptical properties were measured. The assignment of the absolute configuration was established for one compound by single‐crystal X‐ray diffraction method and for the other three by CD spectroscopy. The inhibitory activity against MAO of racemic samples and single enantiomers were evaluated in vitro. Chirality 16:625–636, 2004. © 2004 Wiley‐Liss, Inc.