Synthesis and structural analysis of novel meso-glycosyarylprophyrins for application to oncological phototherapy

The synthesis of 13 novel meso-glycosylarylporphyrins where the carbohydrate moiety is separated from the aryl substituent by a spacer arm is described. These compounds were synthesized by different methods, either by direct glycosylation of the ortho- or para-hydroxyalkoxyarylporphyrin or by condensation of glycosylated aldehyde with pyrrole or meso-(p-tolyl)dipyrromethane. In all cases, a beta configuration was observed. Deprotection of the sugar then followed in a basic medium. The compounds were characterized by a variety of means. A detailed H-1 and C-13 NMR study allowed complete structural determination. The UV-visible and laser desorption mass spectra are presented. Due to their sensitizing abilities, these resultant compounds are of considerable interest for photodynamic therapy.