Efficient Use of the Iron Ortho‐Nitrophenylporphyrin Chloride to Mimic Biological Oxidations of Dimethylaminoantipyrine

Major metabolites of dimethylaminoantipyrine have been synthesized using iron ortho‐nitrophenylporphyrin chloride as biomimetic catalyst. Reactivity of iron tetrakis‐ortho‐nitrophenylporphyrin chloride [Fe(TNO2PP)Cl] has been compared with iron tetrakis‐pentafluorophenylporphyrin chloride and iron tetrakis‐2,6‐dichlorophenylporphyrin chloride using various oxidants such as hydrogen peroxide, iodosobenzene, and cumene hydroperoxide in either protic or aprotic solvent. Effect of imidazole has been showed on the reactivity of Fe(TNO2PP)Cl/cumene hydroperoxide system.

[1]  Jinheung Kim,et al.  Oxidative N-dealkylation reactions by oxoiron(IV) complexes of nonheme and heme ligands. , 2007, Inorganic chemistry.

[2]  J. Groves,et al.  High-valent iron in chemical and biological oxidations. , 2006, Journal of inorganic biochemistry.

[3]  B. Meunier,et al.  Biomimetic Chemical Catalysts in the Oxidative Activation of Drugs , 2004 .

[4]  P. Vérité,et al.  Improvement of a biomimetic porphyrin catalytic system by addition of acids. , 2002, Chemical & pharmaceutical bulletin.

[5]  O. R. Nascimento,et al.  Catalytic activity of nitro- and carboxy-substituted iron porphyrins in hydrocarbon oxidation: Homogeneous solution and supported systems , 2001 .

[6]  F. Guengerich,et al.  Evidence for a 1-Electron Oxidation Mechanism in N-Dealkylation of N,N-Dialkylanilines by Cytochrome P450 2B1 , 1996, The Journal of Biological Chemistry.

[7]  J. Benítez,et al.  Metabolism of aminopyrine and derivatives in man: in vivo study of monomorphic and polymorphic metabolic pathways. , 1995, Xenobiotica; the fate of foreign compounds in biological systems.

[8]  Y. Iamamoto,et al.  Study of catalytic activity of nitro substituted ironporphyrins , 1995 .

[9]  R. McClelland,et al.  Oxidation of aminopyrine by hypochlorite to a reactive dication: possible implications for aminopyrine-induced agranulocytosis. , 1995, Chemical Research in Toxicology.

[10]  Y. Iamamoto,et al.  Study of catalytic activity of nitro substituted iron porphyrins , 1993 .

[11]  T. Traylor,et al.  Alkene epoxidations catalyzed by iron(III), manganese(III), and chromium(III) porphyrins. Effects of metal and porphyrin substituents on selectivity and regiochemistry of epoxidation , 1989 .

[12]  H. Duchstein,et al.  Die Reaktion von Singulett‐Sauerstoff mit 4‐Amino‐3‐pyrazolin‐5‐onen , 1988 .

[13]  W. Robinson,et al.  "Picket fence porphyrins." Synthetic models for oxygen binding hemoproteins. , 1975, Journal of the American Chemical Society.