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1 H and 13 C NMR characteristics of β‐blockers
Author(s) -
ZielińskaPisklak Monika Agnieszka,
Pisklak Dariusz Maciej,
Wawer Iwona
Publication year - 2011
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/mrc.2742
Subject(s) - chemistry , pindolol , acebutolol , atenolol , nuclear magnetic resonance spectroscopy , nmr spectra database , proton nmr , carbon 13 nmr , timolol , stereochemistry , propranolol , spectral line , medicine , astronomy , blood pressure , ophthalmology , biochemistry , receptor , intraocular pressure , physics
The β‐blockers are important drugs and decades of clinical experience proved their high medical status. However, to the best of our knowledge, there is no complete assignment of 1 H and 13 C NMR resonances of popular representatives: acebutolol, alpenolol, pindolol, timolol and propranolol and the published NMR data on carvedilol and atenolol are incorrect. Therefore, 1 H and 13 C NMR spectroscopy was applied for the characterization of a series of β‐adrenolytics: carvedilol (1), pindolol (2), alprenolol (3), acebutolol (4), atenolol (5), propranolol (6) and timolol (7). Two‐dimensional NMR experiments (COSY, HMQC, HMBC, NOESY) allowed the unequivocal assignment of 1 H and 13 C spectra for solution (DMSO‐ d 6 ). Salts and bases can be easily distinguished based on 13 C chemical shifts which are within 65.0–65.5 ppm (OC2) and 46.9–47.0 (NC3) for hydrochlorides and larger, ca. 68.4 ppm (OC2) and 50.3–52.6 (NC3) for bases. NMR data of 1–7 should be included in pharmacopoeias. Copyright © 2011 John Wiley & Sons, Ltd.