BOX A-type monopyrrolic heterocycles modified via the Suzuki-Miyaura cross-coupling reaction

Abstract

The in vivo oxidation of heme yields bilirubin which is further degraded to the bilirubin oxidation end products (BOXes) that are biologically highly active. To study the mode of action and fate of (Z)-2-(4-methyl-5-oxo-3-vinyl-1,5-dihydro-2H-pyrrol-2-ylidene)acetamide (BOX A), the Suzuki-Miyaura cross-coupling reaction allows to introduce various alkenyl- and aryl-substituents in 3-position of the (Z)-2-(4-methyl-5-oxo-1,5-dihydro-2H-pyrrol-2-ylidene)acetamides (BOX A-type monopyrroles). The influence of these groups on structural and NMR-spectroscopic parameters of the central monopyrrolic system is negligible. Special focus has been given to derivatives with 3-positioned aryl substituents carrying trifluoromethyl groups for future in vivo19F NMR studies.