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Chemical Compound Review

Iodosobenzene     iodosylbenzene

Synonyms: Iodosylbenzene, AG-F-84760, WLN: O-I-R, ACMC-209l9l, ANW-31831, ...
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High impact information on iodosylbenzene


Biological context of iodosylbenzene

  • [1-(15)N]-Labeled 4,6-dimethyl-4H-[1,2,5]oxadiazolo[3,4-d]pyrimidine-5,7-dione 1-oxide (1-(15)N1) was easily prepared by nitration of commercially available 6-amino-1,3-dimethyl-1H-pyrimidine-2,4-dione using 15N-enriched nitric acid followed by an intramolecular oxidative cyclization with iodosylbenzene diacetate under mild conditions [5].
  • Regioselective biomimetic oxidation of etodolac with iodosylbenzene catalyzed by halogenated and perhalogenated metalloporphyrins in dichloromethane [6].
  • In the chemical system using meso-tetrakis(pentafluorophenyl)porphyrin iron chloride [Fe(TPFPP)Cl] with iodosylbenzene (PhIO), alpha-arylcarboxylic acids and alpha,alpha,alpha-trisubstituted acetic acids are converted to the corresponding one-carbon-reduced alcohol (I) and carbonyl derivatives (II) via oxidative decarboxylation [7].

Anatomical context of iodosylbenzene


Associations of iodosylbenzene with other chemical compounds


Gene context of iodosylbenzene

  • The patterns of AFB1 oxidation to the two products were modified considerably in systems in which NADPH-P450 reductase was replaced with a flavodoxin or ferredoxin system, iodosylbenzene, or cumene hydroperoxide [14].
  • Oxidation of 3-hydroxypiperidines with iodosylbenzene in water: tandem oxidative Grob fragmentation-cyclization reaction [15].


  1. Diversity in mechanisms of substrate oxidation by cytochrome P450 2D6. Lack of an allosteric role of NADPH-cytochrome P450 reductase in catalytic regioselectivity. Hanna, I.H., Krauser, J.A., Cai, H., Kim, M.S., Guengerich, F.P. J. Biol. Chem. (2001) [Pubmed]
  2. Oxidation of 9-alkylanthracenes by cytochrome P450 2B1, horseradish peroxidase, and iron tetraphenylporphine/iodosylbenzene systems: anaerobic and aerobic mechanisms. Anzenbacher, P., Niwa, T., Tolbert, L.M., Sirimanne, S.R., Guengerich, F.P. Biochemistry (1996) [Pubmed]
  3. Proposed mechanism for the cytochrome P450-catalyzed conversion of aldehydes to hydrocarbons in the house fly, Musca domestica. Reed, J.R., Quilici, D.R., Blomquist, G.J., Reitz, R.C. Biochemistry (1995) [Pubmed]
  4. Iodosylbenzene derivatives as oxygen donors in cytochrome P-450 catalyzed steroid hydroxylations. Gustafsson, J.A., Rondahl, L., Bergman, J. Biochemistry (1979) [Pubmed]
  5. Synthesis and applications of [1-(15)N]-labeled 4,6-dimethyl-4H-[1,2,5]oxadiazolo[3,4-d]pyrimidine-5,7-dione 1-oxide as a useful tool for mechanistic investigations. Sako, M., Yaekura, I., Oda, S., Hirota, K. J. Org. Chem. (2000) [Pubmed]
  6. Regioselective biomimetic oxidation of etodolac with iodosylbenzene catalyzed by halogenated and perhalogenated metalloporphyrins in dichloromethane. Chauhan, S.M., Kandadai, S.A., Sahoo, B. Chem. Pharm. Bull. (2001) [Pubmed]
  7. Application of chemical cytochrome P-450 model systems to studies on drug metabolism--VIII. Novel metabolism of carboxylic acids via oxidative decarboxylation. Komuro, M., Higuchi, T., Hirobe, M. Bioorg. Med. Chem. (1995) [Pubmed]
  8. Stabilization of placental aromatase by dithiothreitol in the presence of oxidizing agents. Kelly, W.G., Stolee, A.H. Steroids (1978) [Pubmed]
  9. Alpha-N-acetylmannosamine (ManNAc) synthesis via rhodium(II)-catalyzed oxidative cyclization of glucal 3-carbamates. Bodner, R., Marcellino, B.K., Severino, A., Smenton, A.L., Rojas, C.M. J. Org. Chem. (2005) [Pubmed]
  10. Synthesis of 21-hydroxy-11,19-oxidopregn-4-ene-3,20-dione and 21-hydroxy-6,19-oxidopregn-4-ene-3,20-dione. Veleiro, A.S., Nevado, M.V., Monteserín, M.C., Burton, G. Steroids (1995) [Pubmed]
  11. The C-C bond cleavage of a lignin model compound, 1,2-diarylpropane-1,3-diol, with a heme-enzyme model catalyst tetraphenylporphyrinatoiron(III)chloride in the presence of tert-butylhydroperoxide. Shimada, M., Habe, T., Umezawa, T., Higuchi, T., Okamoto, T. Biochem. Biophys. Res. Commun. (1984) [Pubmed]
  12. Thromboxane synthase catalyses hydroxylations of prostaglandin H2 analogs in the presence of iodosylbenzene. Hecker, M., Baader, W.J., Weber, P., Ullrich, V. Eur. J. Biochem. (1987) [Pubmed]
  13. Comparative MO-QSAR studies in various species including man. Tyrakowska, B., Cnubben, N.H., Soffers, A.E., Wobbes, T., Rietjens, I.M. Chem. Biol. Interact. (1996) [Pubmed]
  14. Cooperativity in oxidations catalyzed by cytochrome P450 3A4. Ueng, Y.F., Kuwabara, T., Chun, Y.J., Guengerich, F.P. Biochemistry (1997) [Pubmed]
  15. Oxidation of 3-hydroxypiperidines with iodosylbenzene in water: tandem oxidative Grob fragmentation-cyclization reaction. Tada, N., Miyamoto, K., Ochiai, M. Chem. Pharm. Bull. (2004) [Pubmed]
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