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Conformational Analysis of the Anti‐obesity Drug Lorcaserin in Water: How To Take Advantage of Long‐Range Residual Dipolar Couplings
Author(s) -
TrigoMouriño Pablo,
de la Fuente M. Carmen,
Gil Roberto R.,
SánchezPedregal Víctor M.,
NavarroVázquez Armando
Publication year - 2013
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201202509
Subject(s) - residual dipolar coupling , chemistry , residual , hydrogen bond , computational chemistry , dipole , stereochemistry , organic chemistry , molecule , mathematics , algorithm
The conformational state of 8‐chloro‐1‐methyl‐2,3,4,5‐tetrahydro‐1 H ‐3‐benzazepine hydrochloride (lorcaserin) in water has been determined on the basis of one‐bond and long‐range CH residual dipolar coupling (RDC) data along with DFT computations and 3 J HH coupling‐constant analysis. According to this analysis, lorcaserin exists as a conformational equilibrium of two crown‐chair forms, of which the preferred conformation has the methyl group in an equatorial orientation.