Abstract
The X-ray crystal structures of threeβ-blockers of the phenylethanolamine (PEA) class have been determined by single crystal techniques. They are (I): (±)-2-(2-bromo-3,4-dimethoxyphenyl)-2-hydroxy-N-isopropylethylamine hydrochloride; (II): (±)-2-(3-bromo-4,5-dimethoxyphenyl)-2-hydroxy-N-isopropylethylamine methylsulphonate; (III): (±)-2-(2-bromo-4,5-dimethoxyphenyl)-2-hydroxy-N-isopropylethylamine hydrogen oxalate. A conformational energy map of a partially hydrated model cation as a function of the principal torsion angles τ1 and τ2 shows the “transperpendicular” conformer (τ1≈90°, τ2≈180°) to be the most stable. This conformation is adopted by cations of (II) and (III) in their crystals, but for (I), τ1=52.3(6)° is observed. Non-bonded pharmacophoric distances lie within the expected ranges.
Similar content being viewed by others
References
Caillet, J., Claverie, P., and Pullman, B. (1976)Acta Cryst. B32, 2740–2745.
Carpy, A., Leger, J. M., and Colleter, J. C. (1980)Acta Cryst. B36, 2837–2840.
CRC Handbook of Chemistry and Physics (1976–1977) R. C., Weast (ed.) (CRC Press, Cleveland, Ohio).
Diner, S., Malrieu, J. P., and Claverie, P. (1969a)Theoret. Chim. Acta 13, 1–17.
Diner, S., Malrieu, J. P. Jordan, F., and Gilbert, M. (1969b)Theoret. Chim. Acta 15, 100–110.
Duax, W. L. (1979) InMolecular Structure by Diffraction Methods., Vol. 6 (Chapter 11, Pharmacologically Active Small Molecules, (The Chemical Society, London).
Gadret, M., Goursolle, M., Leger, M. M., and Colleter, J. C. (1975)Acta Cryst. B31, 1942–1946.
Hebert, H. (1979) InStudies on the Molecular Structure of α- andβ-Adrenergic Agents (Tryckeri Balder AB, Stockholm).
Howe, R., and Rao, B. S. (1968)J. Med. Chem. 11, 1118–1121.
Jordan, F., Gilbert, M., Malrieu, J. P., and Princelli, U. (1969)Theoret. Chim. Acta 15, 211–224.
Kaufman, J. J. (1977)Int. J. Quantum. Chem. Quantum Biol. Symp. 4, 375–412.
Koorts, J., and Caira, M. (1985a)Acta Cryst. C41, 552–554.
Koorts, J., and Caira, M. (1985b)Acta Cryst. C41, 1372–1374.
Koorts, J. Caira, M., and Venter, D. P. (1986)Acta Cryst. C42, 693–695.
Koorts, J. (1988) Ph.D. thesis, University of Port Elizabeth, Port Elizabeth, South Africa.
Malrieu, J. P., Claverie, P., and Diner, S. (1969)Theoret. Chim. Acta 13, 18–45.
Motherwell, S. (1979)Pluto,A Program for plotting molecular and crystal structures (University of Cambridge, England).
Murray-Rust, P., Murray-Rust, J., Hartley, D., Hallet, P., and Clifton, J. (1984)Acta Cryst. C40, 825–828.
Nardelli, M. (1983)Comput. Chem. 7(3), 95–98.
North, A. C. T., Philips, D. C., and Scott Mathews, F. (1968)Acta Cryst. A24, 351–359.
Port, G. N. J., and Pullman, A. (1973)Theoret. Chim. Acta 31, 231–237.
Pullman, B., Coubeils, J. L., Courriere, Ph., and Gervois, J. P. (1972)J. Med. Chem. 15, 17–23.
Sheldrick, G. M. (1976)Shelx,A System of Computer Programs for X-Ray Structure Determination (University of Cambridge, England).
Structure Determination Package (1982) Frenz, B. A. and Associates Inc., College Station, Texas 77840.
Tollenaere, J. P., Moereels, H., and Raymaekers, L. A. InDrug Design. Vol. X, E. J. Ariens (ed.) (Academic Press, New York), p. 89).
Tollenaere, J. P. (1989) (Janssen Pharmaceutica, Beerse, Belgium), Personal communication.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Le Roux, C., Caira, M.R., Koorts, J. et al. Structures of three isomeric ring-brominated PEA β-blockers: [C13H21BrNO3]+·Cl−, [C13H21BrNO3]+·[CH3SO3]−, and [C13H21BrNO3]+·[C2HO4]− . Journal of Crystallographic and Spectroscopic Research 20, 69–77 (1990). https://doi.org/10.1007/BF01181677
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF01181677