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Chemical Compound Review

IDOBENZENE     iodobenzene

Synonyms: IODOPHENYL, IODOBENZENE, Iodinebenzol, PHENYLIODIDE, iodanylbenzene, ...
 
 
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Disease relevance of iodobenzene

 

High impact information on iodobenzene

 

Biological context of iodobenzene

  • The synthesis was accomplished via Sonogashira coupling of propargyl 2-O-acetyl-5-O-benzyl-3-O-(3, 4-di-O-acetyl-2, 6-di-O-benzyl-alpha-D-glucopyranosyl)-beta-D-ribofuranoside (16) with iodobenzene 18, 22, or 25, followed by deacetylation, phosphorylation, and deprotection [7].
  • Membrane potential dependent binding of scorpion toxin to the action potential sodium ionophore. Studies with a 3-(4-hydroxy 3-[125I] iodophenyl) propionyl derivative [8].
  • The key step of the synthesis of these natural products is a novel type of dimerization of 5 into 4 with iodobenzene diacetate [9].
  • The two spirocentres were constructed via iterative radical oxidative cyclization of hydroxyalkyl dihydropyran 14 and hydroxyalkyl spiroacetal 13 using iodobenzene diacetate and iodine [10].
 

Anatomical context of iodobenzene

  • At least in these cells the inhibitory effect might reflect the action of iodobenzene on a general site, e.g. the lipid matrix of the plasma membrane of the receptor cells [11].
 

Associations of iodobenzene with other chemical compounds

 

Gene context of iodobenzene

  • The addition of the iodophenyl radical impairs both the FA storage and its oxidation, leading to a very high level of free FA [15].
 

Analytical, diagnostic and therapeutic context of iodobenzene

  • Finally, we demonstrate that two of the peptides (L9G and L9A) bind the small molecule iodobenzene when present during crystallization, leaving the general peptide quaternary structure intact but altering the local peptide conformation and certain superhelical parameters [16].
  • Results have been correlated with a concurrent study of remote functionalization reactions induced by iodobenzene diacetate/iodine under ultrasonic irradiation [17].

References

  1. Effect of iodobenzene therapy on mitochondrial activity in 2-thiouracil-induced hypothyroidism in weanling rats. Visvanathan, A., Narayanan, U., Shanmugasundaram, K.R. Res. Commun. Chem. Pathol. Pharmacol. (1983) [Pubmed]
  2. Constitutive regulation of cardiac fatty acid metabolism through peroxisome proliferator-activated receptor alpha associated with age-dependent cardiac toxicity. Watanabe, K., Fujii, H., Takahashi, T., Kodama, M., Aizawa, Y., Ohta, Y., Ono, T., Hasegawa, G., Naito, M., Nakajima, T., Kamijo, Y., Gonzalez, F.J., Aoyama, T. J. Biol. Chem. (2000) [Pubmed]
  3. On the mechanism of action of cytochrome P-450. Spectral intermediates in the reaction with iodosobenzene and its derivatives. Blake, R.C., Coon, M.J. J. Biol. Chem. (1989) [Pubmed]
  4. Thyroid hormonogenesis. Identification of a sequence containing iodophenyl donor site(s) in calf thyroglobulin. Palumbo, G. J. Biol. Chem. (1987) [Pubmed]
  5. Liver glutathione depletion induced by bromobenzene, iodobenzene, and diethylmaleate poisoning and its relation to lipid peroxidation and necrosis. Casini, A.F., Pompella, A., Comporti, M. Am. J. Pathol. (1985) [Pubmed]
  6. Ruthenium-catalyzed Heck-type olefination and Suzuki coupling reactions: studies on the nature of catalytic species. Na, Y., Park, S., Han, S.B., Han, H., Ko, S., Chang, S. J. Am. Chem. Soc. (2004) [Pubmed]
  7. Synthesis of potent agonists of the D-myo-inositol 1,4, 5-trisphosphate receptor based on clustered disaccharide polyphosphate analogues of adenophostin A. de Kort, M., Correa, V., Valentijn, A.R., van der Marel, G.A., Potter, B.V., Taylor, C.W., van Boom, J.H. J. Med. Chem. (2000) [Pubmed]
  8. Membrane potential dependent binding of scorpion toxin to the action potential sodium ionophore. Studies with a 3-(4-hydroxy 3-[125I] iodophenyl) propionyl derivative. Ray, R., Catterall, W.A. J. Neurochem. (1978) [Pubmed]
  9. Simple synthesis of benzofuranoid neolignans from Myristica fragrans. Juhász, L., Kürti, L., Antus, S. J. Nat. Prod. (2000) [Pubmed]
  10. Synthesis of the 1,6,8-trioxadispiro[4.1.5.2]tetradec-11-ene ring system present in the spirolide family of shellfish toxins and its conversion into a 1,6,8-trioxadispiro[4.1.5.2]-tetradec-9-en-12-ol via base-induced rearrangement of an epoxide. Brimble, M.A., Furkert, D.P. Org. Biomol. Chem. (2004) [Pubmed]
  11. Inhibitory and excitatory effects of iodobenzene on the antennal benzoic acid receptor cells of the female silk moth Bombyx mori L. de Brito Sanchez, M.G., Kaissling, K.E. Chem. Senses (2005) [Pubmed]
  12. Effect of catalysis on the stability of metallic nanoparticles: Suzuki reaction catalyzed by PVP-palladium nanoparticles. Narayanan, R., El-Sayed, M.A. J. Am. Chem. Soc. (2003) [Pubmed]
  13. Significance of myocardial uptake of iodine 123-labeled beta-methyl iodophenyl pentadecanoic acid: comparison with kinetics of carbon 11-labeled palmitate in positron emission tomography. Kawamoto, M., Tamaki, N., Yonekura, Y., Magata, Y., Tadamura, E., Nohara, R., Matsumori, A., Sasayama, S., Konishi, J. Journal of nuclear cardiology : official publication of the American Society of Nuclear Cardiology. (1994) [Pubmed]
  14. Pantopaque (ethyl iodophenyl undecylate) intravasation during myelography. Schächter, I., Peyser, E., Guilburd, J.N. Acta neurochirurgica. (1981) [Pubmed]
  15. The intramyocardial fate of [1-14C] palmitate, iodopalmitate and iodophenylpentadecanoate in isolated rat hearts. A contribution to the choice of an iodinated fatty acid as a tracer of myocardial metabolism. Keriel, C.M., Humbert, T.G., Berard, C.R., Marti Batlle, D.S., Le Bars, D., Mathieu, J.P., Luu-Duc, C., Comet, M., Cuchet, P.J. J. Mol. Cell. Cardiol. (1990) [Pubmed]
  16. Structure-based engineering of internal cavities in coiled-coil peptides. Yadav, M.K., Redman, J.E., Leman, L.J., Alvarez-Gutiérrez, J.M., Zhang, Y., Stout, C.D., Ghadiri, M.R. Biochemistry (2005) [Pubmed]
  17. Laurenanes: fenestranes with a twist. Weavers, R.T. J. Org. Chem. (2001) [Pubmed]
 
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