Determination of analogs of sildenafil and vardenafil in foods by column liquid chromatography with a photodiode array detector, mass spectrometry, and nuclear magnetic resonance spectrometry

Abstract

Two analogs of sildenafil and vardenafil in food were detected by column liquid chromatography (LC) with a photodiode array detector. They were isolated by preparative LC; their structures were established by mass spectrometry and nuclear magnetic resonance spectrometry. One analog was found to be methisosildenafil (compound A), 5-(5-(3,5-dimethylpiperazin-1-ylsulfonyl)-2- ethoxyphenyl)-1 -methyl-3-propyl-1 H-pyrazolo[4,3-d]-pyrimidin-7(6H)-one. It is a sildenafil analog with a dimethylpiperazine ring substituted for the methylpiperazine group. The second analog, hydroxyvardenafil (compound B) is reported for the first time in this study. Hydroxyvardenafil's International Union of Pure and Applied Chemistry name is 2-(2-ethoxy-5-(4-(2-hydroxyethyl)- piperazin-1-ylsulfonyl)phenyl)-5-methyl-7-propylimidazo[1,5-f][1,2,4] triazin-4(3H)-one. The novel vardenafil analog has a hydroxyl group added to the ethylpiperazine group.