View PDF Version
 
DOI: 10.1039/A805228J (Paper) Reference Section for: Chem. Commun., 1998, 1907-1908

The synthesis of water soluble isoindoline nitroxides and a pronitroxide hydroxylamine hydrochloride UV–VIS probe for free radicals

(Note: The full text of this document is currently only available in the PDF Version )

Damien A. Reid and Steven E. Bottle

Abstract

The novel water soluble nitroxides 5-trimethylammonio-1,1,3,3-tetramethylisoindolin-2-yloxyl iodide 8 and 5-carboxy-1,1,3,3-tetramethylisoindolin-2-yloxyl 10 are prepared by nitration of the parent nitroxide 2 and bromination of its amine precursor 1; the stable (t1/2 > 580 h in MeOH; ca 72 h in physiological saline) pronitroxide 2-hydroxy-1,1,3,3-tetramethylisoindoline hydrochloride 6 was synthesised by treatment of 2 with HCl gas in dry EtOH and reacts with radicals to form 2; the transformation can be followed by UV–VIS spectroscopy.

References

  1. Free Radicals in Diagnostic Medicine, ed. D. Armstrong, Plenum, New York, 1994, p. 241 Search PubMed.
  2. Oxygen Free Radicals and Scavengers in the Natural Sciences, ed. G. Mozsik, I. Emerit, J. Feher, B. Matkovics and A. Vincze, Akademiai Kindo, Budapest, 1993, p. 63 Search PubMed.
  3. S. M. Hahn, C. M. Krishna, A. Samuni, W. DeGraff, D. O. Cuscela, P. Johnstone and J. B. Mitchell, Cancer Res. (Suppl.), 1994, 54, 2006s Search PubMed.
  4. A. Samuni, D. Godinger, J. Aronovitch, A. Russo and J. B. Mitchell, Biochemistry, 1991, 30, 555 CrossRef CAS.
  5. W. K. Busfield, K. Heiland and I. D. Jenkins, Tetrahedron Lett., 1994, 35, 6541 CrossRef CAS.
  6. W. K. Busfield, I. D. Jenkins and P. Van Le, Polym. Bull., 1996, 36, 435 CrossRef CAS.
  7. D. G. Gillies, L. H. Sutcliffe and X. Wu, J. Chem. Soc., Faraday Trans., 1994, 90, 2345 RSC.
  8. D. G. Gillies, L. H. Sutcliffe, X. Wu and P. S. Belton, Food Chem., 1996, 55, 349 CrossRef CAS Full synthetic details for this species, including yield and characterisation, have not as yet been published.
  9. P. G. Griffiths, G. Moad, E. Rizzardo and D. H. Solomon, Aust. J. Chem., 1983, 36, 397 CAS.
  10. A. S. Micallef and S. E. Bottle, unpublished work.
  11. R. Bolton, D. G. Gillies, L. H. Sutcliffe and X. Wu, J. Chem. Soc., Perkin Trans. 2, 1993, 2049 RSC.
  12. A. M. Giroud and A. Rassat, Bull. Soc. Chem. Fr., 1979, 1–2, II-48.
  13. P. E. James, S. K. Jackson, C. C. Rowlands and B. J. Mile, J. Chem. Soc., Perkin Trans. 2, 1992, 1503 RSC.
  14. J. F. Glockner, H.-C. Chan and H. M. Swartz, Magn. Reson. Med., 1991, 20, 123 CAS.
  15. P. D. Morse, II and A. I. Smirnov, Magn. Reson. Chem., 1995, 33, S46 CAS.
  16. F. Desmar, M. Kueder, S. Rugeli, A. Blinc, M. Sentjure and S. Pecar, J. Magn. Reson., 1991, 95, 281.
  17. S. Dikalov, M. Skatchkov and E. Bassenge, Biochem. Biophys. Res. Commun., 1997, 230, 54 CrossRef CAS.