Advertisement

Chemistry of Heterocyclic Compounds

, Volume 47, Issue 7, pp 877–885 | Cite as

Facile TICl4-catalyzed synthesis of novel 1,2,4-triazoles appended to thiazoles

  • T. Gireesh
  • R. R. KambleEmail author
  • R. K. Hunnur
  • T. Taj
  • M. Y. Kariduraganavar
Article

The reaction of sydnone-derived 3-aryl-5-methyl-1,3,4-oxadiazol-2(3H)-ones with thiourea and α-bromoacetophenone derivatives in the presence of a catalytic amount of TiCl4 produces 2-aryl-4-(4-aryl-1,3-thiazol-2-yl)-5-methyl-2,4-dihydro-3H-1,2,4-triazol-3-ones. The title compounds were screened for their antibacterial and antifungal activity. The toxicity of the compounds was evaluated in terms of mutagenicity, tumorigenicity, and reproductive effects. The drug-relevant properties (ClogP, drug-likeness, and drug score) were calculated, and the structure–activity relationship was discussed.

Keywords

mesoionic compounds sydnones TiCl4 1,3-dipolar cycloaddition 

References

  1. 1.
    R. R. Kamble, P. R. Latthe, and B. V. Badami, Heteroatom Chem., 18, 50 (2007).CrossRefGoogle Scholar
  2. 2.
    M. V. George and C. S. Angadiyavar, J. Org. Chem., 36, 1589 (1971).CrossRefGoogle Scholar
  3. 3.
    R. R. Kamble and B. S. Sudha, J. Heterocycl. Chem., 43, 345 (2006).CrossRefGoogle Scholar
  4. 4.
    A. Varvaresou, A. Tsantili-Kakoulidou, T. Siatra-Papastasikoudi, and E. Tiligada, Arzneim. Forsch., 50, 48 (2000).Google Scholar
  5. 5.
    M. Gokce, B. Cakir, K. Earl, and M. Sahin, Arch. Pharm., 334, 279 (2001).CrossRefGoogle Scholar
  6. 6.
    O. Pintilie, L. Profire, V. Sunel, M. Popa, and A. Pui, Molecules, 12 , 103 (2007).CrossRefGoogle Scholar
  7. 7.
    M. Foroumadi, M. Mirzaei, and A. Shafiee, Pharmazie, 56 , 610 (2001).Google Scholar
  8. 8.
    M. G. Mamolo, V. Falagiani, D. Zampieri, L. Vio, and F. Banfi, Farmaco, 56, 587 (2001).CrossRefGoogle Scholar
  9. 9.
    K. Zamani, K. Faghihi, I. Tofighi, and M. R. Shariatzadeh, Turk. J. Chem., 28, 95 (2004).Google Scholar
  10. 10.
    F. Clerici, D. Pocar, M. Guido, A. Loche, V. Perlini, and M. Brufani, J. Med. Chem., 44, 931 (2001).CrossRefGoogle Scholar
  11. 11.
    T. Önkol, B. Çakir, M. F. Şahin, E. Yildirim, and K. Erol. Turk. J. Chem., 28, 461 (2004).Google Scholar
  12. 12.
    S. Schenone, O. Bruno, A. Ranise, F. Bondavalli, W. Filipelli, G. Falcone, L. Giordano, and M. Vitelli, Bioorg. Med. Chem., 9, 2149 (2001).CrossRefGoogle Scholar
  13. 13.
    L. Labanauskas, V. Kalcas, E. Udrenaite, P. Gaidelis, A. Brukštus, and V. Daukšas, Pharmazie, 56, 617 (2001).Google Scholar
  14. 14.
    S. Oniga, A. E. Parvu, B. Tiperciuc, M. Palage, and O. Oniga, Farmacia, 59, 44 (2011).Google Scholar
  15. 15.
    S. G. Wadodkar, S. O. Jinturkar, and A. V. Kasture, Indian Drugs, 16, 119 (1979).Google Scholar
  16. 16.
    A. Tsuruoka, Y. Kaku, H. Kakinuma, I. Tsukada, M. Yanagisawa, K. Nara, and T. Naito, Chem. Pharm. Bull., 46, 623 (1998).CrossRefGoogle Scholar
  17. 17.
    H. G. Roscoe, D. A. Blickans, and D. Kupfer, US Pat. 3752893 (1971); Chem. Abstr., 79, 96966 (1973).Google Scholar
  18. 18.
    I. Kayagil and S. Demirayak, Phosphorus, Sulfur, Silicon, Relat. Elem., 184, 2197 (2009).CrossRefGoogle Scholar
  19. 19.
    W. Weuffen, T. Pyl, W. Gruebner, and W. D. Juelich, Pharmazie, 20, 629 (1965).Google Scholar
  20. 20.
    C. F. H. Allen and A. Bell, Org. Synth., 24, 12 (1944).Google Scholar
  21. 21.
    R. M. Herbst and J. A. Garrison, J. Org. Chem., 18, 872 (1953).CrossRefGoogle Scholar
  22. 22.
    G. D. Buckley and N. H. Ray, J. Chem. Soc., 1156 (1949).Google Scholar
  23. 23.
    C. Ainsworth and R. G. Jones, J. Am. Chem. Soc., 77, 621 (1955).CrossRefGoogle Scholar
  24. 24.
    W. Otting and H. A. Staab, Liebigs Ann. Chem., 622, 23 (1959).CrossRefGoogle Scholar
  25. 25.
    G. W. Sawdey, J. Am. Chem. Soc., 79, 1955 (1957).CrossRefGoogle Scholar
  26. 26.
    H. C. Brown, H. J. Gisler, Jr., and M. T. Cheng, J. Org. Chem., 31, 781 (1966).CrossRefGoogle Scholar
  27. 27.
    Y. T. Reddy, P. N. Reddy, B. S. Kumar, P. Rajput, N. Sreenivasulu, and B. Rajitha, Phosphorus, Sulfur, Silicon, Relat. Elem., 182, 161 (2007).CrossRefGoogle Scholar
  28. 28.
    H. Valizadeh, H. Gholipur, R. Zarrebin, M. Amiri, and M. R. Sabzi, Phosphorus, Sulfur, Silicon, Relat. Elem., 183, 1552 (2008).CrossRefGoogle Scholar
  29. 29.
    D. Basavaiah and A. J. Rao, Synth. Commun., 32, 195 (2002).CrossRefGoogle Scholar
  30. 30.
    L. Cai, C. Brouwer, K. Sinclair, J. Cuevas, and V. W. Pike, Synthesis, 133 (2006).Google Scholar
  31. 31.
    S. G. Mallur and B. V. Badami, Farmaco, 55, 65 (2000).CrossRefGoogle Scholar
  32. 32.
    C. A. Lipinski, Drug Discovery Today: Technologies, 1, 337, (2004).CrossRefGoogle Scholar
  33. 33.
    OSIRIS Property Explorer, http://www.organic-chemistry.org/prog/peo.
  34. 34.
    S. Emami, A. Kebriaeezadeh, N. Ahangar, and R. Khorasani, Bioorg. Med. Chem. Lett., 21, 655 (2011). CrossRefGoogle Scholar
  35. 35.
    A. T. Sangamwar, U. D. Deshpande, S. S. Pekamwar, and S. M. Vadvalkar, Ind. J. Biotechnol., 6, 389 (2007).Google Scholar

Copyright information

© Springer Science+Business Media, Inc. 2011

Authors and Affiliations

  • T. Gireesh
    • 1
  • R. R. Kamble
    • 1
    Email author
  • R. K. Hunnur
    • 1
  • T. Taj
    • 1
  • M. Y. Kariduraganavar
    • 1
  1. 1.PG Department of Studies in ChemistryKarnatak UniversityDharwadIndia

Personalised recommendations