Photochemical Transformations of Chalcone-Vitamin E Hybrids
PHOTOCHEMICAL TRANSFORMATIONS
DOI:
https://doi.org/10.29356/jmcs.v66i1.1670Keywords:
Photoisomerization, substituent effects, solvent effects, aggregation, deoxyanthocyanidinAbstract
Abstract. Chalcone-vitamin E hybrids 6’-O-tosyl-3,4,5-trimethoxy-δ-tocopherol-chalcone (1), 3,4,5-trimethoxy-δ-tocopherol-chalcone (2), 6’-O-tosyl-3,4,5-trimethoxy-δ-tocopherol-retrochalcone (3) and 3,4,5-trimethoxy-δ-tocopherol-retrochalcone (4) were synthesized as part of a search for new biological activities in these types of derivatives. We report herein on the photoisomerization products of hybrids 1-4, and the effects of the solvent and substitution patterns in producing secondary products such as flavanone 6, 3-deoxyanthocyanidin 8, and hemiketal 10. Photochemically-induced changes are considered important since structural modifications and/or the presence of additional products can affect the biological activity of this type of semisynthetic hybrids.
Resumen. Los híbridos de chalcona-vitamina E, 6’-O-tosil-3,4,5-trimetoxi-δ-tocoferol-chalcona (1), 3,4,5-trimetoxi-δ-tocoferol-chalcona (2), 6’-O-tosil-3,4,5-trimetoxi-δ-tocoferol-retrochalcona (3) y 3,4,5-trimetoxi-δ-tocoferol-retrochalcona (4), fueron sintetizados como parte de la búsqueda de nuevos perfiles de actividad biológica para este tipo de derivados. En este trabajo reportamos los productos de fotoisomerización de los híbridos 1-4, y los efectos del disolvente, así como de distintos patrones de sustitución en la generación de productos secundarios como la flavanona 6, la 3-deoxiantocianidina 8, y el hemicetal 10. Los cambios fotoinducidos son considerados de gran importancia debido a que la modificación en la estructura y/o la presencia de productos adicionales puede afectar la actividad biológica de este tipo de híbridos semisintéticos.
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