Skip to main content

In vivo and in silico pharmacological studies on some new 4-(1,3,4-thiadiazol-2-yl)benzene-1,3-diol analogues

Russian Journal of Bioorganic Chemistry volume 40, pages 352–357 (2014)Cite this article

Abstract

4-(1,3,4-Thiadiazol-2-yl)benzene-1,3-diols 5-substituted in the heterocyclic ring were obtained by the reaction of the commercially available hydrazides or thiosemicarbazides with sulfinylbis[(2,4-dihydroxyphenyl)methanethione]. The synthesized compounds were screened for their influence on CNS in an in vivo model. Computer aided prediction tools were used for the evaluation of toxicological properties. Additionally, based on the Lipinski filters, the drug-likeness of compounds was assessed. They revealed that the compounds possess properties which can suggest favorable pharmacokinetics in the body after oral admission.

This is a preview of subscription content, access via your institution.

Access options

Buy single article

Instant access to the full article PDF.

USD 39.95

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

Abbreviations

CA:

carbonic anhydrases

CNS:

central nervous system

logP :

logarithm of partition coefficient of compound between n-octanol and water

PM3:

parametric method 3

STB:

sulfinylbis[2,4-dihydroxyphenyl)methanethione]

References

  1. Foroumadi, A., Soltani, F., Moallemzadeh-Haghighi, H., and Shafiee, A., Arch. Pharm., 2005, vol. 338, pp. 112–116.

    CAS  Article  Google Scholar 

  2. Chou, J.Y., Lai, S.Y., Pan, S.L., Jow, G.M., Chern, J.W., and Guh, J.H., Biochem. Pharmacol., 2003, vol. 66, pp. 115–124.

    CAS  PubMed  Article  Google Scholar 

  3. Chapleo, C.B., Myers, M., Myers, P.L., Saville, J.F., Smith, A.C.B., and Stillings, M.R., J. Med. Chem., 1986, vol. 29, pp. 2273–2280.

    CAS  PubMed  Article  Google Scholar 

  4. Schenone, S., Brullo, C., Bruno, O., Bondavalli, F., Ranise, A., Filippelli, W., Rinaldi, B., Capuano, A., and Falcone, G., Bioorg. Med. Chem., 2006, vol. 14, pp. 1698–1705.

    CAS  PubMed  Article  Google Scholar 

  5. Mullican, M.D., Wilson, M.W., Conner, D.T., Kostlan, C.R., Schrier, D.J., and Dyer, R.D., J. Med. Chem., 1993, vol. 36, pp. 1090–1099.

    CAS  PubMed  Article  Google Scholar 

  6. Labanauskas, L., Kalcas, V., Udrenaite, E., Gaidelis, P., Brukstus, A., and Dauksas, V., Pharmazie, 2001, vol. 56, pp. 617–619.

    CAS  PubMed  Google Scholar 

  7. Clerici, F., Pocar, D., Guido, M., Loche, A., Perlini. V., and Brufani, M., J. Med. Chem., 2001, vol. 44, pp. 931–936.

    CAS  PubMed  Article  Google Scholar 

  8. Supuran, C.T. and Scozzafava, A., Eur. J. Med. Chem., 2000, vol. 35, pp. 867–874.

    CAS  PubMed  Article  Google Scholar 

  9. Turkmen, H., Durgun, M., Yilmaztekin, S., Emul, M., Innocenti, A., Vullo, D., Scozzafava, A., and Supuran, C.T., Bioorg. Med. Chem. Lett., 2005, vol. 15, pp. 367–372.

    CAS  PubMed  Article  Google Scholar 

  10. Matysiak, J. and Malicki, Z., Russ. J. Bioorg. Chem., 2007, vol. 33, pp. 594–601.

    CAS  Article  Google Scholar 

  11. Matysiak, J., Chem. Pharm. Bull., 2006, vol. 54, pp. 988–991.

    CAS  PubMed  Article  Google Scholar 

  12. Matysiak, J. and Opolski, A., Bioorg. Med. Chem., 2006, vol. 14, pp. 4483–4489.

    CAS  PubMed  Article  Google Scholar 

  13. Rzeski, W., Matysiak, J., and Kandefer-Szerszen-, M., Bioorg. Med. Chem., 2007, vol. 15, pp. 3201–3207.

    CAS  PubMed  Article  Google Scholar 

  14. Lipinski, C.A., Lombardo, F., Dominy, B.W., and Feeney, P.J., Adv. Drug. Deliv. Rev., 1997, vol. 23, pp. 3–25.

    CAS  Article  Google Scholar 

  15. Maunz, A., Gütlein, M., Rautenberg, M., Vorgrimmler, D., Gebele, D., and Helma, C., Front. Pharmacol., 2013, vol. 4, pp. 1–10.

    Google Scholar 

  16. Stillings, M.R., Welbourn, A.P., and Walter, D.S., J. Med. Chem., 1986, vol. 29, pp. 2280–2284.

    CAS  PubMed  Article  Google Scholar 

  17. Dogan, H.N., Duran, A., Rollas, S., Sener, G., Uysal, M.K., and Gülen, D., Bioorg. Med. Chem., 2002, vol. 10, pp. 2893–2898.

    CAS  PubMed  Article  Google Scholar 

  18. Boissier, J.R., Tardy, J., and Diverres, J.C., Med. Exp., 1960, vol. 3, pp. 81–84.

    CAS  Google Scholar 

  19. Boissier, J.R. and Simon, P., Physiol. Behav., 1967, vol. 2, pp. 447–448.

    Article  Google Scholar 

  20. Aron, C., Simon, P., Larousse, C., and Boissier, J.R., Neuropharmacology, 1971, vol. 10, pp. 459–469.

    CAS  PubMed  Article  Google Scholar 

  21. Porsolt, R.D., Bertin, A., Deniel, M., and Jalfre, M., Arch. Int. Pharmacodyn. Thér., 1977, vol. 229, pp. 327–336.

    CAS  PubMed  Google Scholar 

  22. Witkin, L., Heubner, G., Galdi, F., O’Keefe, E., Spitaletta, F., and Plumer, A., J. Pharmacol. Exp. Ther., 1961, vol. 133, pp. 400–408.

    CAS  PubMed  Google Scholar 

  23. Corne, S.J., Pickering, R.W., and Warner, B.T., Br. J. Pharmacol., 1963, vol. 20, pp. 106–120.

    CAS  Google Scholar 

  24. PC Spartan Pro ver. 1.08. Pro User’s Guide, Wavefunction Inc., California, 1999.

  25. ChemOffice, Cambridge Soft Corporation, Cambridge, USA, 2006.

  26. http:/lazar.in-silico.de

  27. Helma, C., Mol. Divers., 2006, vol. 10, pp. 147–158.

    CAS  PubMed  Article  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Toxicology, Medical University, Chodźki 8, Lublin, 20-093, Poland

    E. Jagiełło-Wójtowicz, A. Chodkowska & K. Pawłowski

  2. Department of Chemistry, University of Life Sciences, Lublin, Akademicka 15, Lublin, 20-950, Poland

    A. Niewiadomy & K. Sarna

  3. Institute of Industrial Organic Chemistry, Annopol 6, Warszawa, 03-236, Poland

    A. Niewiadomy

Authors
  1. E. Jagiełło-Wójtowicz
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. A. Niewiadomy
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. A. Chodkowska
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. K. Pawłowski
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. K. Sarna
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to A. Niewiadomy.

Additional information

The article is published in the original.

Rights and permissions

Reprints and Permissions

About this article

Verify currency and authenticity via CrossMark

Cite this article

Jagiełło-Wójtowicz, E., Niewiadomy, A., Chodkowska, A. et al. In vivo and in silico pharmacological studies on some new 4-(1,3,4-thiadiazol-2-yl)benzene-1,3-diol analogues. Russ J Bioorg Chem 40, 352–357 (2014). https://doi.org/10.1134/S1068162014030078

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1068162014030078

Keywords

  • 1,3,4-thiadiazole
  • influence on CNS
  • Lipinski’s rule
  • in silico