Photoactivatable prodrugs of butyric acid based on new coumarin fused oxazole heterocycles

• Main Author: Soares, Ana M. S.
• Publication Date: 2017
• Other Authors: Hungerford, Graham, Costa, Susana P. G., Gonçalves, M. Sameiro T.
• Format: Article
• Language: eng
• Source: Repositórios Científicos de Acesso Aberto de Portugal (RCAAP)
• Download full: https://hdl.handle.net/1822/44064
• topic: Prodrugs; Coumarins; Oxazoles; Butyric acid; Photocleavable protecting groups; Photolysis; Ciências Naturais::Ciências Químicas; Science & Technology

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.