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

Condensation of pyrrole with a benzaldehyde and 4-pyridinecarboxaldehy de 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-aminop henyl(phenyl)- or 4-aminophenyl(phenyl)(4-pyridyl)porphyrins. Twelve o f the porphyrins are new, but all 27 are fully characterized by H-1 NM R; resonances for every proton within each of the phenyl, pyridyl, and pyrrole rings are assigned. Trends in UV-VIS data are discussed, whil e IR and mass spectral data are noted for selected porphyrins.