Studies of the degradation mechanism of pyrrolo[3,4-c] pyridine-1,3(2H)-dione derivatives with analgesic activity: isolation and identification of products and summary.
Within the framework of the studies concerning the decomposition of N-substituted derivatives of 4-alkoxy-6-methyl-1H-pyrrolo[3,4-c]pyridine-1,3(2H)-dione, the isolation of the alkaline hydrolysis product was performed (pH 10.5, room temperature). Subsequently, based on NMR spectra and two-dimensional spectra, the chemical structure of the isolated compounds was established. The interpretation of COSY, HSQC and HMBC spectra proved that the C1-N2 bond of the pyrrolopyridinedione ring undergoes cleavage under the influence of OH ions and generates a product which is an isonicotinic acid derivative. Owing to the analysis of previous studies, including results presented in this paper, the decomposition mechanism of the compounds studied could be determined.
Department of Pharmaceutical Chemistry, Poznań University of Medical Sciences, Grunwaldzka 6, 60-780 Poznań, Poland. imuszals@ump.edu.pl
Izabela
I
Muszalska
D000700:Analgesics / Q000737:chemistry*; D015195:Drug Design; D004355:Drug Stability; D006863:Hydrogen-Ion Concentration; D006868:Hydrolysis; D017665:Hydroxyl Radical / Q000737:chemistry; D007539:Isonicotinic Acids / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D011758:Pyrroles / Q000737:chemistry*; D013678:Technology, Pharmaceutical / Q000379:methods
D000700:Analgesics; D007539:Isonicotinic Acids; D011758:Pyrroles; D017665:Hydroxyl Radical