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PORPHYRIN CHEMISTRY PERTAINING TO THE DESIGN OF ANTICANCER DRUGS .1. THE SYNTHESIS OF PORPHYRINS CONTAINING MESO-PYRIDYL AND MESO-SUBSTITUTED PHENYL FUNCTIONAL-GROUPS

TitlePORPHYRIN CHEMISTRY PERTAINING TO THE DESIGN OF ANTICANCER DRUGS .1. THE SYNTHESIS OF PORPHYRINS CONTAINING MESO-PYRIDYL AND MESO-SUBSTITUTED PHENYL FUNCTIONAL-GROUPS
Publication TypeJournal Article
Year of Publication1994
AuthorsMeng, GZG, James, BR, Skov, KA
JournalCanadian Journal of Chemistry-Revue Canadienne De Chimie
Volume72
Pagination1894-1909
Date PublishedSep
Type of ArticleArticle
ISBN Number0008-4042
KeywordsMETALLOPORPHYRINS, MODEL, NUCLEAR MAGNETIC-RESONANCE, OXYGEN, TETRAARYLPORPHYRINS, TUMORS
Abstract

Condensation of pyrrole with a benzaldehyde and 4-pyridinecarboxaldehyde mixture yields the six possible meso-substituted phenyl or pyridyl porphyrins. Nitration of four of these has yielded 13 other porphyrins containing one to four 4-nitrophenyl moieties, and SnCl2 reduction of eight of these nitrophenylporphyrins gives the corresponding 4-aminophenyl(phenyl)- or 4-aminophenyl(phenyl)(4-pyridyl)porphyrins. Twelve of the porphyrins are new, but all 27 are fully characterized by H-1 NMR; resonances for every proton within each of the phenyl, pyridyl, and pyrrole rings are assigned. Trends in UV-VIS data are discussed, while IR and mass spectral data are noted for selected porphyrins.

URL<Go to ISI>://A1994PJ99400002