Multigram synthesis of a water-soluble porphyrazine and derived seco-porphyrazine labeling agents.
Porphyrazine III has been synthesized on a large scale (18.4 g), with minimal chromatographic purification by employing a novel one-pot, 3-step sequence. Two dinitrile precursors I and II, the latter of which consisted of a mixture of geometric isomers, were transformed, via the corresponding pyrroline diimines, into a mixture of III and the octa-Ar1-porphyrazine. Isolated macrocycle III was subsequently transformed into IV, a water-soluble seco-porphyrazine suitable for the labeling of biological vectors.
Guinchard
Xavier
X
Department of Chemistry, Imperial College London, London SW7 2AZ, England.
Fuchter
Matthew J
MJ
Ruggiero
Andrea
A
Duckworth
Brian J
BJ
Barrett
Anthony G M
AG
Hoffman
Brian M
BM
D008665:Metalloporphyrins / Q000737:chemistry*; D015394:Molecular Structure; D017319:Photosensitizing Agents / Q000737:chemistry; D012995:Solubility; D014867:Water / Q000737:chemistry*
D008665:Metalloporphyrins; D017319:Photosensitizing Agents; D014867:Water