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Enantiomers of 2‐[(Acylamino)ethyl]‐1,4‐benzodiazepines, Potent ligands of κ‐opioid receptor: Chiral chromatographic resolution, configurational assignment, and biological activity
Author(s) -
Azzolina O.,
Collina S.,
Linati L.,
Anzini M.,
Cappelli A.,
Scheideler M.A.,
Sbacchi M.
Publication year - 2001
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.1185
Subject(s) - chemistry , enantiomer , chiral column chromatography , chirality (physics) , resolution (logic) , absolute configuration , stereochemistry , selectivity , opioid receptor , stereoselectivity , chiral derivatizing agent , stereoisomerism , chiral stationary phase , opioid , chromatography , receptor , organic chemistry , molecule , chiral symmetry breaking , physics , biochemistry , quantum mechanics , artificial intelligence , computer science , nambu–jona lasinio model , quark , catalysis
Compounds 2a and 3a–e are racemic 2‐[(acylamino)ethyl]‐1,4‐benzodiazepines, tifluadom analogs, with high affinity and selectivity towards the κ‐opioid receptor. We describe the enantiomeric separation of all compounds through liquid chromatography with chiral stationary phases, as well as the resolution of the enantiomers of the most interesting compounds, 2a and 3a , by the semipreparative column Chiralpak AD. The configuration of the resolved enantiomers was investigated: the comparative study of CD and 1 H NMR spectra shows that compounds (−)‐ 2a and (−)‐ 3a have the same absolute configuration of (+)‐(S)‐tifluadom. A study on the stereoselective interaction with opiate receptors is reported. Chirality 13:606–612, 2001. © 2001 Wiley‐Liss, Inc.