Synthesis of gold(I), silver(I) and copper(I) complexes containing substituted (2-aminophenyl)phosphines. Molecular structures of [AuI(2-H2NC6H4PPh2)], [AuI{(±)-2-H2NC6H4PMePh}] and (±)-[Cu(2-H2NC6H4PPh2)2];PF6

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Peter Papathanasiou, Geoffrey Salem, Paul Waring and Anthony C. Willis


Abstract

Linear gold(I) complexes of type [AuI(L)] and [AuL2]I (L = 2-H2NC6H4PPhR, R = Me or Ph) have been prepared by the reaction of the appropriate ligand with [NBun4][AuI2] in ethanol. The neutral ligand L is co-ordinated to the metal centre via the phosphorus donor atom. The structures of the complexes [AuI(2-H2NC6H4PPh2)] and [AuI{(±)-2-H2NC6H4PMePh}] have been confirmed by X-ray analyses with the latter, but not the former, complex exhibiting auriophilicity. Metathesis of these compounds with NH4PF6 gave the corresponding hexafluorophosphate salts [AuLn]PF6 (n = 1 or 2). Tetrahedral complexes of the type [MLn]PF6 (L = 2-H2NC6H4PPhR; R = Ph, M = Ag or Cu, n = 2 or 3; R = Me, M = Cu, n = 2 or 3; R = Me, M = Ag, n = 3) have also been prepared via reaction of the appropriate ligand with [Cu(NCMe)4]PF6 in acetonitrile or AgNO3 in ethanol followed by metathesis with NH4PF6. The molecular structure of (±)-[Cu(2-H2NC6H4PPh2)2]PF6 has been confirmed by X-ray crystallography. All of the complexes have been shown by NMR spectroscopy to undergo facile ligand-exchange reactions in solution. These complexes are seen as potential anticancer agents. Preliminary biological studies have shown them to be active against three mouse tumour cell lines in vitro with cytotoxicities of certain of these complexes being comparable to that of cis-diamminedichloroplatinum(II), cisplatin, and bis[1,2-bis(diphenylphosphino)ethane]gold(I) iodide.


References

  1. J. A. L. Palmer and S. B. Wild, Inorg. Chem., 1983, 22, 4054 CrossRef CAS.
  2. G. Salem, A. Schier and S. B. Wild, Inorg. Chem., 1988, 27, 3029 CrossRef CAS.
  3. S. J. Berners-Price, M. A. Mazid and P. J. Sadler, J. Chem. Soc., Dalton Trans., 1984, 969 RSC.
  4. S. J. Berners-Price, C. Brevard, A. Pagelot and P. J. Sadler, Inorg. Chem., 1985, 24, 4287.
  5. S. J. Berners-Price, C. Brevard, A. Pagelot and P. J. Sadler, Inorg. Chem., 1986, 25, 596 CrossRef.
  6. S. J. Berners-Price and P. J. Sadler, Inorg. Chem., 1986, 25, 3822 CrossRef CAS.
  7. S. J. Berners-Price, R. K. Johnson, C. K. Mirabelli, L. F. Faucette, F. L. McCabe and P. J. Sadler, Inorg. Chem., 1987, 26, 3383 CrossRef CAS.
  8. A. Del Zotto, G. Nardin and P. J. Rigo, J. Chem. Soc., Dalton Trans., 1995, 3343 RSC.
  9. S. J. Berners-Price and P. J. Sadler, Struct. Bonding (Berlin), 1988, 70, 27 CAS.
  10. T. W. Hambley, Chem. Aust., 1991, 58, 154 Search PubMed.
  11. G. D. Hoke, G. F. Rush, G. E. Bossard, J. V. McArdle, B. D. Jensen and C. K. Mirabelli, J. Biol. Chem., 1988, 263, 11 203 CAS.
  12. P. F. Smith, G. D. Hoke, D. W. Alberts, P. J. Bugelski, S. Lupo, C. K. Mirabelli and G. F. Rush, J. Pharmacol. Exp. Ther., 1989, 249, 944 Search PubMed.
  13. H. Schmidbauer, Chem. Ber., 1997, 130, 647 CAS.
  14. M. K. Cooper, J. M. Downes, P. A. Duckworth, M. C. Kerby, R. J. Powell and M. D. Soucek, Inorg. Synth., 1989, 25, 129 CAS.
  15. C. E. Barclay, G. Deeble, R. J. Doyle, S. A. Elix, G. Salem, T. L. Jones, S. B. Wild and A. C. Willis, J. Chem. Soc., Dalton Trans., 1995, 57 RSC.
  16. L. Baker, R. C. Bott, G. A. Bowmaker, P. C. Healy, B. W. Skelton, P. Schwerdtfeger and A. H. White, J. Chem. Soc., Dalton Trans., 1995, 1341 RSC.
  17. G. J. Kubas, Inorg. Synth., 1979, 19, 90 CAS.
  18. L. Hudson and F. C. Hay, Practical Immunology, 3rd edn., Blackwell Scientific Publications, London, 1989, p. 430 Search PubMed.
  19. SIR 92, A. Altomare, M. Cascarano and C. Guagliardi, J. Appl. Crystallogr., 1993, 26, 343 Search PubMed.
  20. SHELXS 86, G. M. Sheldrick, Crystallographic Computing 3, eds. G. M. Sheldrick, C. Kruger and R. Goddard, Oxford University Press, 1985, pp. 175–189 Search PubMed.
  21. DIRDIF 94, P. T. Beurskens, G. Admiraal, G. Beurskens, W. P. Bosman, R. de Gelder, R. Israel and J. M. M. Smits, DIRDIF program system, Technical Report of the Crystallography Laboratory, University of Nijmegen, 1994.
  22. D. T. Cromer and J. T. Waber, International Tables for X-Ray Crysallography, Kynoch Press, Birmingham, 1974, vol. 4, Table 2.2A Search PubMed.
  23. J. A. Ibers and W. C. Hamilton, Acta Crystallogr., 1964, 17, 781 CrossRef.
  24. D. C. Creagh and W. J. McAuley, International Tables for Crystallography, ed. A. J. C. Wilson, Kluwer Academic Publishers, Boston, 1992, vol. C Search PubMed.
  25. D. C. Creagh and J. H. Hubbell, International Tables for Crystallography, ed. A. J. C. Wilson, Kluwer Academic Publishers, Boston, 1992, vol. C, Table 4.2.4.3, pp. 200–206 Search PubMed.
  26. TEXSAN, Crystal Structure Analysis Package, Molecular Structure Corporation, The Woodlands, TX, 1985 and 1992.
  27. W. J. Geary, Coord. Chem. Rev., 1971, 7, 81 CrossRef CAS.
  28. H. Schmidbauer, Chem. Soc. Rev., 1995, 24, 391 RSC.
  29. S. J. Berners-Price, P. J. Sadler and C. Brevard, Magn. Reson. Chem., 1990, 28, 1990.
  30. S. J. Berners-Price, C. K. Mirabelli, R. K. Johnson, M. R. Mattern, F. L. McCabe, L. F. Faucette, C. M. Sung, S. M. Mong, P. J. Sadler and S. T. Crooke, Cancer Res., 1986, 46, 5486 CAS.
  31. R. M. Snyder, C. K. Mirabelli, R. K. Johnson, C. M. Sung, L. F. Faucette, F. L. McCabe, J. P. Zimmerman, M. Whitman, J. C. Hempel and S. T. Crooke, Cancer Res., 1986, 46, 5054 CAS.
  32. C. K. Mirabelli, D. T. Hill, L. F. Faucette, F. L. McCabe, G. R. Girard, D. B. Bryan, B. M. Sutton, J. O. Bartus, S. T. Crooke and R. K. Johnson, J. Med. Chem., 1987, 30, 2181 CrossRef CAS.
  33. S. J. Berners-Price, R. E. Norman and P. J. Sadler, J. Inorg. Biochem., 1988, 33, 285 CrossRef CAS.
  34. C. K. Mirabelli, R. K. Johnson, C. M. Sung, L. F. Faucette, K. Muirhead and S. T. Crooke, Cancer Res., 1985, 45, 32 CAS.
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