Publicação
Photoactivatable prodrugs of butyric acid based on new coumarin fused oxazole heterocycles
| Resumo: | New coumarin fused oxazoles were investigated as photosensitive units for carboxylic acid groups using butyric acid as a model compound. 6-Oxo-6H-benzopyrano[6,7-d]oxazol-8-yl)methyl derivatives possessing various (hetero)aromatic substituents at position 2 of the heterocyclic system were used in the synthesis of ester conjugates of butyric acid. Photolysis at selected wavelengths in methanol/HEPES buffer (80:20) solutions, monitored by HPLC/UV and 1H NMR, produced the complete release of butyric acid. The shorter irradiation times for cleavage at longer wavelengths occurred for the conjugate with a 4-oxo-4H-benzopyran-2-yl substituent and thus (6-oxo-2-(4-oxo-4H-benzopyran-2-yl)-6H-benzopyrano[6,7-d]oxazol-8-yl)methyl has potential as a candidate photosensitive moiety for butyric acid prodrugs. |
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| Autores principais: | Soares, Ana M. S. |
| Outros Autores: | Hungerford, Graham; Costa, Susana P. G.; Gonçalves, M. Sameiro T. |
| Assunto: | Prodrugs Coumarins Oxazoles Butyric acid Photocleavable protecting groups Photolysis |
| Ano: | 2017 |
| País: | Portugal |
| Tipo de documento: | artigo |
| Tipo de acesso: | acesso aberto |
| Instituição associada: | Universidade do Minho |
| Idioma: | inglês |
| Origem: | RepositóriUM - Universidade do Minho |
| Resumo: | New coumarin fused oxazoles were investigated as photosensitive units for carboxylic acid groups using butyric acid as a model compound. 6-Oxo-6H-benzopyrano[6,7-d]oxazol-8-yl)methyl derivatives possessing various (hetero)aromatic substituents at position 2 of the heterocyclic system were used in the synthesis of ester conjugates of butyric acid. Photolysis at selected wavelengths in methanol/HEPES buffer (80:20) solutions, monitored by HPLC/UV and 1H NMR, produced the complete release of butyric acid. The shorter irradiation times for cleavage at longer wavelengths occurred for the conjugate with a 4-oxo-4H-benzopyran-2-yl substituent and thus (6-oxo-2-(4-oxo-4H-benzopyran-2-yl)-6H-benzopyrano[6,7-d]oxazol-8-yl)methyl has potential as a candidate photosensitive moiety for butyric acid prodrugs. |
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