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Chiroptical properties and absolute configuration of pyrroloisoquinoline antidepressants
Author(s) -
Maryanoff Bruce E.,
McComsey David F.,
Craig J. Cymerman
Publication year - 1998
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.26
Subject(s) - chemistry , enantiomer , absolute configuration , circular dichroism , chirality (physics) , cotton effect , sign (mathematics) , stereochemistry , spectral line , crystallography , analytical chemistry (journal) , organic chemistry , chiral symmetry , mathematics , quantum mechanics , astronomy , nambu–jona lasinio model , quark , mathematical analysis , physics
Abstract Circular dichroism (CD) spectra were determined for the bioactive (+)‐enantiomers of 1 · HCl, 3 · HCl, and 4 · HBr to characterize the chiroptical properties of these pyrroloisoquinoline antidepressants. The compounds showed a low‐intensity negative CD band with much fine structure between 252 and 272 nm, a medium negative CD band with fine structure between 215 and 225 nm, and a high‐intensity negative CD maximum between 198 and 203 nm. Except for amplitude variation, the three CD spectra were essentially superimposable in sign and position of the bands. The CD curves for the (−)‐enantiomers of 1 · HCl and 4 · HBr were opposite in sign and comparable within 5% to the (+)‐enantiomers. The results are consistent with the previously assigned (Maryanoff et al. J. Med. Chem. 30:1433–1454, 1987) absolute configurations of (6 S, 10b R ) for 1 and 3 , and (6 R, 10b R ) for 4 . Chirality 10:169–172, 1998. © 1998 Wiley‐Liss, Inc.