Synthesis, Chiral Resolution and Enantiomers Absolute Configuration of 4-Nitropropranolol and 7-Nitropropranolol

We recently identified 6-nitrodopamine and other nitro-catecholamines (6-nitrodopa, 6-nitroadrenaline), indicating that the endothelium has the ability to nitrate the classical catecholamines (dopamine, noradrenaline, and adrenaline). In order to investigate whether drugs could be subject to the same nitration process, we synthesized 4-nitro- and 7-nitropropranolol as probes to evaluate the possible nitration of the propranolol by the endothelium. The separation of the enantiomers in very high yields and excellent enantiopurity was achieved by chiral HPLC. Finally, we used Riguera's method to determine the absolute configuration of the enantiomers, through double derivatization with MPA and NMR studies.

Automated summary

Researchers have discovered that the endothelium is capable of nitration of classical catecholamines (dopamine, noradrenaline, and adrenaline) and synthesized 4-nitro- and 7-nitropropranolol as probes to investigate the nitration of propranolol by the endothelium. Chiral HPLC was used to separate the enantiomers with high yields and excellent enantiopurity. Riguera's method, through double derivatization with MPA and NMR studies, was employed to determine the absolute configuration of the enantiomers.