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1H and 13C NMR studies of some steroidal neuromuscular blocking drugs: solution conformations and dynamics

✍ Scribed by Lee Fielding

Publisher
John Wiley and Sons
Year
1998
Tongue
English
Weight
306 KB
Volume
36
Category
Article
ISSN
0749-1581

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✦ Synopsis

The 1H and 13C NMR spectra of the steroidal neuromuscular blocking drugs pancuronium bromide, vecuronium bromide, rocuronium bromide and Org. 9487 are presented. The 13C NMR spectra are fully assigned. NOE data and variable-temperature studies show that there is considerable conformational freedom in both the ring A substituents and the sterically more crowded ring D substituents. The barrier to nitrogen-ring inversion in the non-quaternized piperidine ring is ca. 10È11 kcal mol~1. The quaternized ring D piperidine (or (*GE) pyrollidine) rings are free to rotate with respect to the steroid. The vicinal couplings 13COÈOÈCÈ1H, ca. 4 Hz, suggest that the ester moieties have similar rotational freedom to simple esters.

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