High impact information on iodosylbenzene

• We conclude that the P450 systems utilizing NADPH-P450 reductase, cumene hydroperoxide, and iodosylbenzene use similar but distinct chemical mechanisms [1].
• Oxidation of 9-alkylanthracenes by cytochrome P450 2B1, horseradish peroxidase, and iron tetraphenylporphine/iodosylbenzene systems: anaerobic and aerobic mechanisms [2].
• Hydrogen peroxide, cumene hydroperoxide, and iodosobenzene were able to support hydrocarbon production from [3H]24:1 aldehyde in place of O2 and NADPH for short incubation times [3].
• Evidence for cytochrome P-450 involvement in iodosylbenzene-sustained androstenedione hydroxylation included inhibition by substrates and modifiers of cytochrome P-450 [4].
• The mechanism of cytochrome P-450 catalyzed steroid hydroxylations in rat liver microsomes has been investigated by employing derivatives of iodosylbenzene as oxygen donors [4].

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

• Cumene hydroperoxide, sodium periodate and iodosobenzene were not able to support aromatization by placental microsomes in the absence of NADPH or molecular oxygen [8].

Associations of iodosylbenzene with other chemical compounds

• [reaction: see text] Glucal 3-carbamates 1 and 7 underwent oxidative cyclization with iodobenzene diacetate or iodosobenzene in the presence of Rh2(OAc)4, providing mannosamine 2-N,3-O-oxazolidinones [9].
• Hydroxylation at C-21 was effected with iodosobenzene (from phenyliodosodiacetate and methanolic potassium hydroxide) on a 20-ketopregnane [10].
• The C-C bond of the lignin model compound 1,2-bis(4-ethoxy-3-methoxyphenyl) propane-1,3-diol was oxidatively cleaved by catalysis of iron-porphyrins in the presence of tert-butylhydroperoxide or iodosylbenzene at a room temperature [11].
• Thromboxane synthase catalyses hydroxylations of prostaglandin H2 analogs in the presence of iodosylbenzene [12].
• Finally, possibilities for the extrapolation from rat to other species, of the MO-QSAR for the rate of in vitro C4 hydroxylation of a series of aniline derivatives converted in an iodosobenzene-supported microsomal cytochrome P450 system, were investigated [13].

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].

References