Bis(N,N-dimethylamino)methane has been shown to be a convenient reagent for the aminomethylation of chlorophyll a derivatives. Methylpheophorbide a (in enol form) and chlorin e 6 13-amides were aminomethylated with bis(N,N-dimethylamino)methane. Reactivity of methylpheophorbide a exo-ring and chlorin e 6 13-amides vinyl group were shown to be different. Selective methylpheophorbide a exo-ring aminomethylation was realized and isomerization of the exo-ring aminomethylation product with rhodochlorin 15-acrylic derivative formation was studied. The action of bis(N,N-dimethylamino)-methane in the presence of weak acid has been shown to be a simple and effective synthetic procedure to obtain a new chlorin e 6 derivative with two N,N-dimethylaminomethyl substituents in the vinyl group. The aminomethylation products' high yields, the simplicity of the procedure, the use of metal-free chlorines and the possible synthesis of new compounds, were found to be the main advantages of using bis(N,N-dimethylamino)methane as an aminomethylation reagent in chlorophyll a derivatives' chemistry.
It has been shown that aminomethylation of the vinyl group in Zn complexes of chlorophyll a phorbine derivatives can be accomplished under the action of bis (N,N-dimethylamino
A series of terpenophenol-chlorin conjugates where terpenophenolic fragment has amide bond with macrocycle of methylpheophorbide a, formed by amidation of 13(2)-ester group were obtained by interaction of methylpheophorbide a and ortho-aminomethyl derivatives of 2-isobornyl-4-methylphenol. The substances investigated ability to interact with the cell membrane was shown in blood erythrocytes surface structure with scanning electron microscope. The conjugates studied were established to have antioxidant and membrane protective properties resulted from inhibiting H2O2-induced erythrocytes hemolysis and decrease of lipid peroxidation secondary product accumulation.
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