184775-11-9Relevant academic research and scientific papers
Synthesis of a fluorine analog of hematoporphyrin by ring closure
Omote, Masaaki,Ando, Akira,Takagi, Toshiyuki,Koyama, Mayumi,Kumadaki, Itsumaro
, p. 89 - 93 (2007/10/03)
Benzyl 3,5-dimethyl-2-pyrrolecarboxylate (1) was converted to 4-(2,2,2-trifluoro-1-hydroxyethyl) derivative (2) on treatment with trifluoro-acetaldehyde ethyl hemiacetal in the presence of zinc chloride. After protection of the hydroxy group, 2 was converted to benzyl 4-methyl-3-(2,2,2-trifluoro-1-methoxyethyl)2-pyrrolecarboxylate (9) and benzyl 5-acetoxymethyl-3-methyl-4-(2,2,2-trifluoro-1-methoxyethyl)-2-pyrrolecarboxylate (10). Both esters were condensed to a dipyrrolomethane compound (11), which was debenzylated, decarboxylated, and condensed with a bottom half of the porphyrin to give a hexafluorohematoporphyrin derivative (14), potentially useful for photodynamic therapy of cancer.
Synthesis of a fluorine analog of hematoporphyrin by ring closure
Omote, Masaaki,Ando, Akira,Takagi, Toshiyuki,Koyama, Mayumi,Kumadaki, Itsumaro
, p. 13961 - 13970 (2007/10/03)
Benzyl 3,5-dimethyl-2-pyrrolecarboxylate (1) was converted to 4-(2,2,2-trifluoro-1-hydroxyethyl) derivative (2) on treatment with trifluoroacetaldehyde ethyl hemiacetal in the presence of zinc chloride. After protection of the hydroxyl group with a methyl group, 2 was converted to benzyl 4-methyl-3-(2,2,2-trifluoro-1-methoxyethyl)-2-pyrrolecarboxylate (9) and benzyl 5-acetoxymethyl-3-methyl-4-(2,2,2-trifluoro-1-methoxyethyl)-2-pyrrolec arboxylate (10). Both esters were condensed to dipyrylmethane compound 11, which was debenzylated, decarboxylated, and condensed with a bottom half of the porphyrin to give hexafluorohematoporphyrin derivative 14, potentially useful for photodynamic therapy of cancer.
