Application of Trihydroxyindole Reaction to Methanesulfonanilides: Fluorometric Analysis for Soterenol and Mesuprine
| Autor: | Donna M. Walker, Terry T. Kensler, Dana Brooke |
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| Rok vydání: | 1976 |
| Předmět: |
Mesylates
Sulfonamides Indoles Time Factors Stereochemistry Reaction scheme Pharmaceutical Science Ascorbic Acid Hydrogen-Ion Concentration Fluorometric Analysis Medicinal chemistry Fluorescence chemistry.chemical_compound chemistry Ethanolamines Phenethylamines Methods Potassium Anilides Fluorometry Oxidation-Reduction Fluorescence response Iodine Methyl group |
| Zdroj: | Journal of Pharmaceutical Sciences. 65:763-765 |
| ISSN: | 0022-3549 |
| DOI: | 10.1002/jps.2600650540 |
| Popis: | Methanesulfonanilides, like soterenol and mesuprine, which are bioisosteric with adrenergic catecholamines, form fluorescent species when subjected to the trihydroxyindole reaction. Presumably, the fluorescence is due to adrenolutin‐like species formed from aminochrome intermediates. Fluorescence was not induced in a relative of soterenol where a methyl group was added to the sulfonamido nitrogen, a fact that suggests the presence of a quinoid intermediate in the reaction scheme of soterenol. A ring isomer of soterenol, where the methanesulfonamido and hydroxyl groups were interchanged, produced only about 5% as much fluorescence response as soterenol. The soterenol counterparts to isoproterenol and isoproterenolsulfonic acid did not produce fluorescence when treated like soterenol. This finding and the fact that response was linear with concentration for soterenol and mesuprine suggest that a fluorometric analysis could be developed for these methanesulfonanilides. |
| Databáze: | OpenAIRE |
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