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The synthesis of two monosubstituted meso ‐tetraphenylporphine sulfonates
Author(s) -
Sun Yizhen,
Martell Arthur E.,
Chen Dian,
Macfarlane Ronald D.,
Mcneal Catherine J.
Publication year - 1986
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570230562
Subject(s) - chemistry , porphyrin , moiety , ethylenediamine , platinum , ring (chemistry) , molecule , derivatization , palladium , combinatorial chemistry , medicinal chemistry , stereochemistry , organic chemistry , catalysis , high performance liquid chromatography
This paper describes the synthesis and characterization of two novel meso ‐tetrakis(4‐sulfophenyl)‐21 H ,‐23 H ‐porphine (TPPS 4 ) derivatives in which one of the phenyl rings is substituted with an anticancer agent. Several advantages of monosubstitution are pointed out: the higher efficiency of synthetic steps involving the derivatization of one, rather than several, functional group per porphyrin molecule, and the greater solubility and ease of purification of monosubstituted tetraphenylporphines. The new compounds have 5‐fluorouracil and cis dichloroethylenediamineplatinum ( cis ‐platinum) substituted in the meta positions of one of the phenyl rings in TPPS 4 . The palladium analog of the cis ‐platinum dervative which contains two Pd(II) atoms per molecule ‐ one coordinated with the ethylenediamine moiety, and the other coordinated at the center of the porphyrin ring, was also prepared.