Skip to main content
SpringerLink
Log in

On reduction of the drug diflunisal in non-aqueous media

  • Original Paper
  • Published:
Monatshefte für Chemie - Chemical Monthly Aims and scope Submit manuscript

Abstract

The electrochemical reduction of diflunisal was studied in dimethyl sulfoxide on static mercury drop electrode. Diflunisal yields one irreversible wave at −1.2 V (vs. Ag | AgCl | 1 M LiCl electrode) due to the reduction of the carboxylic functional group in the molecule. The electrochemical properties of the drug were compared with the ones of the chlorinated analogue. The study is based on cyclic voltammetry, tast polarography, and constant potential electrolysis. The experimental findings are supported by molecular orbital calculations. The mechanism of reduction of the carboxylic moiety was found to involve two electrons and two protons. The reduction pathway leads to formation of an aldehyde derivative.

Graphical Abstract

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6

Similar content being viewed by others

References

  1. Beltagi AM (2009) J Appl Electrochem 39:2375

    Article  CAS  Google Scholar 

  2. Sayin F, Kır S (2001) J Pharm Biomed Anal 25:153

    Article  CAS  Google Scholar 

  3. Davies RO (1983) Pharmacotherapy 3:9S

    CAS  Google Scholar 

  4. Tiribilli C, Giannarelli S, Sokolová R, Valášek M (2014) In: Navrátil T, Fojta M, Pecková K (eds), XXXIV. Moderní elektrochemické metody. Srsenová L.–Best servis Ústí n. L., p. 202

  5. Hanna J, Ruyle WV, Matzuk AR, Kelly KW, Witzel BE, Holtz WJ, Houser RA, Shen TY, Sarett LH (1978) J Med Chem 21:1093

    Article  Google Scholar 

  6. Adamski-Werner SL, Palaninathan SK, Sacchettini JC, Kelly JW (2004) J Med Chem 47:355

    Article  CAS  Google Scholar 

  7. Trsková R, Rychlovský P, Němcová I, Turek P (1996) Pharmazie 51:550

    Google Scholar 

  8. Pérez-Ruiz T, Martinez Lozano C, Tomas V (1998) Fresenius J Anal Chem 361:492

  9. Ding Y, Garcia CD (2006) Electroanalysis 18:2202

    Article  CAS  Google Scholar 

  10. British Pharmacopoeia (2009) Volume I and II, Medicines and Healthcare products Regulatory Agency (MHRA). London, p 1937 and 8652

  11. Shaaban H, Górecki T (2011) Anal Chim Acta 702:136

    Article  CAS  Google Scholar 

  12. Shaalan RA, Belal TS (2013) Sci Pharm 81:713

    Article  CAS  Google Scholar 

  13. Gupta VK, Jain R, Radhpyari K, Jadon N, Agarwal S (2011) Anal Biochem 408:179

    Article  CAS  Google Scholar 

  14. Lohmann W, Karst U (2008) Anal Bioanal Chem 391:79

    Article  CAS  Google Scholar 

  15. Švecová H, Součková J, Pyszková M, Svítková J, Labuda J, Skopalová J, Barták P (2014) Eur J Lipid Sci Technol 116:1247

    Article  Google Scholar 

  16. Jaklová Dytrtová J, Šestáková I, Jakl M, Navrátil T (2009) Electroanalysis 21:573

  17. Sokolová R, Bulíčková J, Parisová M, Navrátil T, Gál M (2013) The Adsorption of Phospholipids at the Interface. In: Navrátil T, Fojta M, Pecková K (eds), XXXIII. Moderní elektrochemické metody. Srsenová L. - Best servis Ústí n. L., p. 187

  18. Lund H, Hammerich O (2001) Organic Electrochemistry, 4th edn. Marcel Dekker Inc, New York

    Google Scholar 

  19. Barrads RG, Kutowy O, Shoesmith DW (1974) Electrochim Acta 19:49

    Article  Google Scholar 

  20. Hatzipanayioti D, Karaliota A, Kamariotaki M, Veneris A (1998) Transition Met Chem 23:407

    Article  CAS  Google Scholar 

  21. Hofmann JC, Robertson PM, Ibl N (1972) Tetrahedron Lett 33:3433

    Article  Google Scholar 

  22. Harrison JA, Shoesmith DW (1971) J Electroanal Chem 32:125

    Article  CAS  Google Scholar 

  23. Pospíšil L, Teplý F, Gál M, Adriaenssens L, Horáček M, Severa L (2010) Phys Chem Chem Phys 12:1550

    Article  Google Scholar 

  24. Vyskočil V, Barek J (2009) Crit Rev Anal Chem 39:173

    Article  Google Scholar 

  25. Zuman P (2000) Electroanalysis 12:1187

    Article  CAS  Google Scholar 

  26. Gál M, Kielar F, Sokolová R, Ramešová Š, Kolivoška V (2013) Eur J Inorg Chem 3217

  27. Sokolová R, Machníková E, Fiedler J, Hromadová M, Giannarelli S, Pospíšil L (2006) ECS Trans-Electrochem Soc 2:75

    Article  Google Scholar 

  28. M’Halla F, Pinson J, Savéant J-M (1980) J Am Chem Soc 102:4120

    Article  Google Scholar 

  29. Sokolová R, Hromadová M, Fiedler J, Pospíšil L, Giannarelli S, Valášek M (2008) J Electroanal Chem 622:211

    Article  Google Scholar 

  30. Houser KJ, Bartak DE, Hawley MD (1973) J Am Chem Soc 95:6033

    Article  CAS  Google Scholar 

  31. Sokolová R, Hromadová M, Ludvík J, Pospíšil L, Giannarelli S (2010) Electrochim Acta 55:8336

    Article  Google Scholar 

  32. Ji C, Peters DG, Davidson ER (2001) J Electroanal Chem 500:3

    Article  CAS  Google Scholar 

  33. Sokolová R, Gál M, Valášek M (2012) J Electroanal Chem 685:33

    Article  Google Scholar 

  34. Heyrovský J, Kůta J (1965) Principles of Polarography. Publishing house of the Czechoslovak Academy of Sciences, New York

    Book  Google Scholar 

  35. Rieger PH, Bernal I, Reinmuth WH, Fraenkel GK (1963) J Am Chem Soc 85:683

    Article  CAS  Google Scholar 

  36. Wagenknecht JH (1972) J Org Chem 37:1513

    Article  CAS  Google Scholar 

  37. Elving PJ, Bennett CE (1954) J Am Chem Soc 76:1412

    Article  CAS  Google Scholar 

  38. Elving PJ, Bennett CE (1954) J Electrochem Soc 101:520

    Article  CAS  Google Scholar 

  39. Furman NH, Norton DR (1954) Anal Chem 26:1111

    Article  CAS  Google Scholar 

  40. Coulson DM, Crowell WR (1952) J Am Chem Soc 74:1290

    Article  CAS  Google Scholar 

  41. Šelešovská-Fadrná R, Navrátil T (2007) Vlček M 52:911

    Google Scholar 

  42. Elving PJ, Bennett CE (1954) Anal Chem 26:1572

    Article  CAS  Google Scholar 

  43. Adamski-Werner SL, Palaninathan SK, Sacchettini JC, Kelly JW (2004) J Med Chem 47:355

    Article  CAS  Google Scholar 

Download references

Acknowledgments

This work is supported by the Academy of Sciences of the Czech Republic (M200401201).

Author information

Authors and Affiliations

  1. Department of Chemistry and Industrial Chemistry, University of Pisa, Via Moruzzi 3, 56124, Pisa, Italy

    Chiara Tiribilli & Stefania Giannarelli

  2. J. Heyrovský Institute of Physical Chemistry of ASCR, Dolejškova 3, 18223, Prague, Czech Republic

    Romana Sokolová

  3. Institute of Nanotechnology, Karlsruhe Institute of Technology, Hermann-von-Helmholtz-Platz 1, 76344, Eggenstein-Leopoldshafen, Germany

    Michal Valášek

Authors
  1. Chiara Tiribilli
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Romana Sokolová
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Stefania Giannarelli
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Michal Valášek
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Romana Sokolová.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Tiribilli, C., Sokolová, R., Giannarelli, S. et al. On reduction of the drug diflunisal in non-aqueous media. Monatsh Chem 146, 807–812 (2015). https://doi.org/10.1007/s00706-014-1390-7

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-014-1390-7

Keywords

Search

Navigation