The structure of azaprophen, which was originally assigned by 1H NMR analysis, was confirmed by X-ray crystallography. A comparison of 13C NMR isotropic chemical shift data for azaprophen in the solid state and in CDCl3 and DMSO-d6 solution was used to correlate solution and solid-state conformation as determined by the X-ray data. The data suggested that the solid-state and solution conformation of azaprophen were similar. The observed solid-state structure was also compared to low-energy conformations identified by molecular-mechanics calculations. A comparison of azaprophen and atropine radioligand binding in guinea pig ileum, rat heart, rat brain, and in CHO cells expressing transfected m1 and m3 receptors was conducted. Azaprophen is more active than atropine in all preparations except the m3 receptor expressed in CHO cells. However, like atropine, it does not provide major discrimination among the muscarinic receptor subtypes
Crystal, solution, and molecular modeling structural properties and muscarinic antagonist activity of azaprophen
Carroll, F., Abraham, P., Mascarella, S., Singh, P., Moreland, CG., Sankar, SS., Kwon, YW., & Triggle, DJ. (1991). Crystal, solution, and molecular modeling structural properties and muscarinic antagonist activity of azaprophen. Journal of Medicinal Chemistry, 34(4), 1436-1440.