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Conformational structure of propranolol: A β‐adrenergic blocking drug studied by NMR and PCILO methods
Author(s) -
Kulkarni Vithal M.,
Vasanthkumar N.,
Saran Anil,
Govil Girjesh
Publication year - 2009
Publication title -
international journal of quantum chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.484
H-Index - 105
eISSN - 1097-461X
pISSN - 0020-7608
DOI - 10.1002/qua.560160711
Subject(s) - chemistry , moiety , propranolol , stereochemistry , proton , proton nmr , molecule , bicyclic molecule , blocking (statistics) , resonance (particle physics) , computational chemistry , crystallography , organic chemistry , medicine , physics , statistics , mathematics , particle physics , quantum mechanics
The conformational structure of propranolol, a β‐adrenergic blocking drug, has been investigated by pcilo calculations and 270‐MHz proton nuclear magnetic resonance in D 2 O solution. The molecules coexist in at least two conformational states in solution with a low energy barrier. Both preferred conformations have extended structures which allow a three‐point drug‐receptor binding involving the aromatic moiety, the β‐hydroxyl group, and ‐NH + 2 groups of propranolol. The previously postulated “rigid” bicyclic structure does not exist to an appreciable extent in D 2 O solution.