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.
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Department of Pharmaceutical Chemistry, Poznań University of Medical Sciences, Grunwaldzka 6, 60-780 Poznań, Poland. imuszals@ump.edu.pl
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