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Synthesis and antimicrobial activity of novel gold(I) N-heterocyclic carbene complexes

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Abstract

Benzimidazolium salts and six anionic gold–NHC complexes (NHC = N,N’-dialkylbenzimidazol-2-ylidene) were prepared and characterized. Novel [Au(NHC)2]AuCl2-type complexes were prepared in good yields from silver–NHC complexes by treatment with [AuCl(PPh3)], following the commonly used silver carbene transfer route. All compounds were characterized using 1H and 13C NMR spectroscopy, elemental analysis, and IR. The gold complexes showed antimicrobial activity against Gram-positive/negative and fungal strains.

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References

  1. Bourissou D, Guerret O, Gabbai FP, Bertrand G (2000) Chem Rev 100:39

    Article  CAS  Google Scholar 

  2. Hahn FE (2006) Angew Chem Int Ed 45:1348

    Article  CAS  Google Scholar 

  3. Kantchev EAB, O’Brien CJ, Organ MG (2007) Angew Chem Int Ed 46:2768

    Article  CAS  Google Scholar 

  4. Hermann WA, Elison M, Fischer J, Köcher C, Artus GRJ (1995) Angew Chem Int Ed 34:2371

    Article  Google Scholar 

  5. Peris E, Mata J, Loch JA, Crabtree RH (2001) Chem Commun 201:201

    Article  Google Scholar 

  6. Melaiye A, Sun Z, Hindi K, Milsted A, Ely D, Reneker DH, Tessier CA, Youngs WJ (2005) J Am Chem Soc 127:2285

    Article  CAS  Google Scholar 

  7. Garrison JC, Tessier CA, Youngs WJ (2005) J Organomet Chem 690:6008

    Article  CAS  Google Scholar 

  8. Skander M, Retailleau P, Bourrié B, Schio L, Mailliet P, Marinetti A (2010) J Med Chem 53:2146

    Article  CAS  Google Scholar 

  9. Patil S, Deally A, Gleeson B, Müller-Bunz H, Paradisi F, Tacke M (2010) Appl Organomet Chem 24:781

    Article  CAS  Google Scholar 

  10. Ray L, Katiyar V, Raihan MJ, Nanavati H, Shaikh MM, Ghosh P (2006) Eur J Inorg Chem 3724

  11. Gung BW, Bailey LN, Craft DT, Barnes CL, Kirschbaum K (2010) Organometallics 29:3450

    Article  CAS  Google Scholar 

  12. Ray S, Mohan R, Singh JK, Samantaray MK, Shaikh MM, Panda D, Ghosh P (2007) J Am Chem Soc 129:15042

    Article  CAS  Google Scholar 

  13. Ray L, Shaikh MM, Ghosh P (2007) Dalton Trans 4546

  14. Blodgett RC, Heuer MA, Pietrusko RG (1984) Semin Arth Rheum 255

  15. Chaffman M, Brogden RN, Heel RC, Speight TM, Avery GS (1984) Drugs 27:378

    Article  CAS  Google Scholar 

  16. McKeage MJ, Maharaj L, Berners-Price SJ (2002) Coord Chem Rev 232:127

    Article  CAS  Google Scholar 

  17. Rigobello MP, Scutari G, Folda A, Bindoli A (2004) Biochem Pharmacol 67:689

    Article  CAS  Google Scholar 

  18. Rigobello MP, Scutari G, Boscolo R, Bindoli A (2002) Br J Pharmacol 136:1162

    Article  CAS  Google Scholar 

  19. Raubenheimer HG, Cronje S (2008) Chem Soc Rev 37:1998

    Article  CAS  Google Scholar 

  20. Bonati F, Burini A, Pietroni BR, Bovio B (1989) J Organomet Chem 375:375

    Article  Google Scholar 

  21. Raubenheimer HG, Lindeque L, Cronje S (1996) J Organomet Chem 511:177

    Article  CAS  Google Scholar 

  22. de Frémont P, Scott NM, Stevens ED, Nolan SP (2005) Organometallics 24:2411

    Article  Google Scholar 

  23. de Frémont P, Marion N, Nolan SP (2009) J Organomet Chem 694:551

    Article  Google Scholar 

  24. Fructos, Belderrain TR, de Frémont P, Scott NM, Nolan SP, Diaz-Requejo MM, Perez PJ (2005) Angew Chem Int Ed 44:5284

    Article  CAS  Google Scholar 

  25. Marion N, Nolan SP (2008) Chem Soc Rev 37:1776

    Article  CAS  Google Scholar 

  26. Boogaerts IIF, Nolan SP (2010) J Am Chem Soc 132:8858

    Article  CAS  Google Scholar 

  27. Teles JH, Brode S, Chabanas M (1998) Angew Chem Int Ed 37:1415

    Article  CAS  Google Scholar 

  28. Lin IJB, Vasam CS (2005) Can J Chem 83:812

    Article  CAS  Google Scholar 

  29. Raubenheimer HG, Cronje S (2008) Chem Soc Rev 37:1998

    Article  CAS  Google Scholar 

  30. Gaillard S, Nun P, Slawin AMZ, Nolan SP (2010) Organometallics 29:5402

    Article  CAS  Google Scholar 

  31. Schneider SK, Hermann WA, Herdtweck E (2003) Z Anorg Allg Chem 629:2363

    Article  CAS  Google Scholar 

  32. Partyka DV, Esswein AJ, Zeller M, Hunter AD, Gray TG (2007) Organometallics 26:3279

    Article  CAS  Google Scholar 

  33. Barnard PJ, Berners-Price SJ (2007) Coord Chem Rev 251:1889

    Article  CAS  Google Scholar 

  34. Ray L, Shaikh MM, Ghosh P (2008) Inorg Chem 47:230

    Article  CAS  Google Scholar 

  35. Krishnamurthy D, Karver MR, Fiorillo E, Orru V, Stanford SM, Bottini N, Barrios M (2008) J Med Chem 51:4790

    Article  CAS  Google Scholar 

  36. Lee KM, Lee CK, Lin IJB (1997) Angew Chem Int Ed 36:1850

    Article  CAS  Google Scholar 

  37. Doğan Ö, Demir S, Özdemir İ, Çetinkaya B (2011) Appl Organomet Chem 25:163

    Article  Google Scholar 

  38. Yasar S, Özdemir İ, Çetinkaya B, Renaud JL, Bruneau C (2008) Eur J Org Chem 12:2142

    Article  Google Scholar 

  39. Özdemir İ, Demir S, Çetinkaya B, Gourlaouen C, Maseras F, Bruneau C, Dixneuf PH (2008) J Am Chem Soc 130:1156

    Article  Google Scholar 

  40. Jothibasu R, Huynh HV, Koh LL (2008) J Organomet Chem 693:374

    Article  CAS  Google Scholar 

  41. Özdemir İ, Temelli N, Günal S, Demir S (2010) Molecules 15:2203

    Article  Google Scholar 

  42. Özdemir İ, Denizci A, Öztürk HT, Çetinkaya B (2004) Appl Organomet Chem 18:318

    Article  Google Scholar 

  43. Böhler C, Stein D, Donati N, Grützmacher H (2002) New J Chem 26:1291

    Article  Google Scholar 

  44. Raubenheimer HG, Cronje S (2001) J Organomet Chem 617–618:170

    Article  Google Scholar 

  45. Poyatos M, Sanau M, Peris E (2003) Inorg Chem 42:2572

    Article  CAS  Google Scholar 

  46. Wang HMJ, Lin IJB (1998) Organometallics 17:972

    Article  CAS  Google Scholar 

  47. Clinical and Laboratory Standards Institute (2003) Methods for dilution, antimicrobial susceptibility tests for bacteria that grow aerobically; approved standard—7th en; CLSI document M7-A7. Clinical and Laboratory Standards Institute, Wayne

  48. Clinical and Laboratory Standards Institute (2002) Reference method for broth dilution, antifungal susceptibility testing of yeasts; approved standard—2nd edn; NCCLS document M27-A2 (ISBN 1-56238- 469-4). NCCLS, Wayne

  49. Hindler J, Hochstein L, Howell A (1992) Preparation of routine media and reagents used in antimicrobial susceptibility testing, part 1. McFarland standards. In: Isenberg HD (ed) Clinical microbiology procedures handbook, vol 1. American Society for Microbiology, Washington, DC, pp. 5.19.1–5.19.6

  50. Nemcsok D, Wichmann K, Frenking G (2004) Organometallics 23:3640

    Article  CAS  Google Scholar 

Download references

Acknowledgments

This work was financially supported by the Technological and Scientific Research Council of Turkey TUBİTAK [TBAG (108T411)] and İnönü University Research Fund (İÜBAP: 2009/13).

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Correspondence to İsmail Özdemir.

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Doğan, Ö., Kaloğlu, N., Demir, S. et al. Synthesis and antimicrobial activity of novel gold(I) N-heterocyclic carbene complexes. Monatsh Chem 144, 313–319 (2013). https://doi.org/10.1007/s00706-012-0812-7

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  • DOI: https://doi.org/10.1007/s00706-012-0812-7

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