Synthesis of 10, 11-Dihydroxydihydroquinidine N-oxide, a New Metabolite of Quinidine. Preparation and 1H-nmr Spectroscopy of the Metabolites of Quinine and Quinidine and Conformational Analysis via 2D COSY NMR Spectroscopy
| Autor: | James M. Cook, Hernando Diaz-Arauzo, Douglas J. Christie |
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| Rok vydání: | 1990 |
| Předmět: |
Pharmacology
Quinidine Quinine Stereochemistry Chemistry Spectrum Analysis Metabolite Organic Chemistry Molecular Conformation Oxide Pharmaceutical Science Chemical synthesis Analytical Chemistry chemistry.chemical_compound Complementary and alternative medicine Drug Discovery medicine Molecular Medicine Molecule Spectroscopy Two-dimensional nuclear magnetic resonance spectroscopy medicine.drug |
| Zdroj: | Journal of Natural Products. 53:112-124 |
| ISSN: | 1520-6025 0163-3864 |
| DOI: | 10.1021/np50067a015 |
| Popis: | The first synthesis of 10,11-dihydroxydihydroquinidine N-oxide [7b], a recently isolated metabolite of quinidine, was accomplished in three steps from 1b. The related congener 7a in the quinine series was also prepared, as well as two other analogues 3a and 4a. In addition, the previously reported human metabolites 2a, 5a, and 6a of quinine [1a] and those 2b, 3b, 4b, 5b, and 6b of quinidine [1b] were synthesized. The chemical shift and coupling constants for all of the metabolites of quinine and quinidine were assigned via 2D COSY 1H-nmr spectroscopy. Moreover, the conformations of these metabolites in solution were found to parallel those of the parent alkaloids, quinine [1a] and quinidine [1b], respectively. |
| Databáze: | OpenAIRE |
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