On the Amazing Reactivity of the Ranelate Ion: New Applications of an Old Antiosporotic Drug

Ranelate ion, the major component of an old antiosporotic drug, exhibits a unusual chemical structure encompassing a thiophene ring with two carboxylic groups, a cyanonitrile substituent, and a nitrile diacetate group; it undergoes decarboxylation at the thiophene carbon‐5 position in acidic solutio...

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Veröffentlicht in:ChemistrySelect (Weinheim) 2019-12, Vol.4 (47), p.13926-13931
Hauptverfasser: Rocha, Julio C., Sihn, Luca M., Uchiyama, Mayara K., Ribeiro, Marcos A., Franco, Maurício P., Braga, Ataualpa A. C., Silveira, Alceu T., Toma, Henrique E.
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Sprache:eng
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Zusammenfassung:Ranelate ion, the major component of an old antiosporotic drug, exhibits a unusual chemical structure encompassing a thiophene ring with two carboxylic groups, a cyanonitrile substituent, and a nitrile diacetate group; it undergoes decarboxylation at the thiophene carbon‐5 position in acidic solutions, yielding a photoreactive (H5Ran) species which converts into a remarkably stable blue dithiophene dye in the presence of UV light and air. Ranelic acid exhibits a unusual chemical structure encompassing a thiophene ring with two carboxylic groups, a cyanonitrile substituent, and a nitrile diacetate group; in acidic solutions it undergoes decarboxylation at the thiophene carbon‐5 position, releasing carbon dioxyde and generating a photoreactive (H5Ran) species which converts, in the presence of UV light and air, into a remarkably stable blue dithiophene dye, keeping the several substituents in a rather symmetric arrangement.
ISSN:2365-6549
2365-6549
DOI:10.1002/slct.201904149