Open AccessSynthèse et analyse structurale de nouvelles méso-arylporphyrines glycosylées en vue de l'application en photothérapie des cancers
Author(s) -
Olivier Gaud,
Robert Granet,
Mourad Kaouadji,
Pierre Krausz,
JeanClaude Blais,
G. Bolbach
Publication year - 1996
Publication title -
canadian journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.323
H-Index - 68
eISSN - 1480-3291
pISSN - 0008-4042
DOI - 10.1139/v96-053
Subject(s) - chemistry , glycosylation , glycosyl , substituent , pyrrole , aldehyde , stereochemistry , moiety , proton nmr , organic chemistry , biochemistry , catalysis
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 β configuration was observed. Deprotection of the sugar then followed in a basic medium. The compounds were characterized by a variety of means. A detailed 1 H and 13 C 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. Key words: porphyrins, glycosylations, phototherapy, cancer.