Research & Teaching Faculty

Default Header Image

Chemical modification of chlorophyll a: Synthesis of new regiochemically pure benzoporphyrin and dibenzoporphyrin derivatives

TitleChemical modification of chlorophyll a: Synthesis of new regiochemically pure benzoporphyrin and dibenzoporphyrin derivatives
Publication TypeJournal Article
Year of Publication1997
AuthorsMa, LF, Dolphin, D
JournalCanadian Journal of Chemistry-Revue Canadienne De Chimie
Volume75
Pagination262-275
Date PublishedMar
Type of ArticleArticle
ISBN Number0008-4042
Keywords(di)benzoporphyrins, (di)vinylporphyrins, chlorins, CHLOROPHYLL, CONVERSION, Diels-Alder, ESTERS, photodynamic, PHOTODYNAMIC THERAPY, ROUTE, therapy
Abstract

Starting from pheophorbide a methyl ester (5), a degradation product of chlorophyll a, routes for the preparation of 3-vinylporphyrins 6 and 9 and of an [A,C]-divinylporphyrin 16 are described. These porphyrins were obtained as a result of chemical modification of 5 on ring D and the exocyclic ring E. Diels-Alder reactions of these (di)vinylporphyrins with dimethyl acetylenedicarboxylate, to afford new regiochemically pure benzoporphyrin derivatives 29 and 30 and dibenzoporphyrin derivative 33 for potential use as sensitizers in photodynamic therapy of tumors, were also investigated.

URL<Go to ISI>://A1997XD81300003