Skip to main content
SpringerLink
Log in

Synthesis, Structure, and Antiradical Activity of New Methano[1,3]Thiazolo[2,3-d][1,3,5]Benzoxa-Diazocine Derivatives

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

The reaction of 2,6-methano[1, 3, 5]benzoxadiazocines, obtained in Biginelli reaction, with chloroacetic acid derivatives produced previously unknown tricyclic methano[1,3]thiazolo[2,3-d][1,3,5]benz-oxadiazocines, the structure of which was proved by 1Н NMR spectroscopy and X-ray structural analysis. The methano[1,3]thiazolo[2,3-d][1,3,5]benzoxadiazocines showed no antiradical activity in contrast to the starting 2,6-methano[1,3,5]benzoxadiazocines.

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

Similar content being viewed by others

References

  1. P. Wipf and V. Cunningham, Tetrahedron Lett., 36, 7819 (1995).

    Article  CAS  Google Scholar 

  2. R. Gupta, A. K. Gupta, S. Paul, and P. L. Kachroo, Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem., 34B, 151 (1995).

    CAS  Google Scholar 

  3. G. J. Grover, S. Dzwonczyk, D. M. McMulltn, C. S. Normadinam, and S. J. Moreland, J. Cardiovasc. Pharmacol., 26, 289 (1995).

    Article  CAS  Google Scholar 

  4. S. V. Vdovina and V. A. Mamedov, Russ. Chem. Rev., 77, 1017 (2008). [Usp. Khim., 77, 1091 (2008).]

    Article  CAS  Google Scholar 

  5. M. B. Deshmukh, P. V. Anbhule, S. D. Jadhav, A. R. Mali, S. S. Jagtap, and S. A. Deshmukh, Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem., 46B, 1545 (2007).

    CAS  Google Scholar 

  6. A. Saini, S. Kumar, and J. S. Sandhu, Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem., 46B, 1690 (2007).

    CAS  Google Scholar 

  7. A. Saini, S. Kumar, and J. S. Sandhu, Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem., 46B, 1886 (2007).

    Google Scholar 

  8. J. J. Ma, X. H. Zang, X. Zhou, C. Wang, J. C. Li, and Q. Li, Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem., 46B, 2045 (2007).

    CAS  Google Scholar 

  9. F. Makaev, E. Styngach, V. Muntyanu, S. Pogrebnoi, Z. Rybkovskaya, and A. Barba, Russ. J. Org. Chem., 43, 1512 (2007). [Zh. Org. Khim., 43, 1518 (2007).]

    Article  CAS  Google Scholar 

  10. V. N. Pathak, R. Gupta, and B. Varshney, Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem., 47B, 434 (2008).

    CAS  Google Scholar 

  11. S. K. Kundu, A. Majee, and A. Hajra, Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem., 48B, 408 (2009).

    CAS  Google Scholar 

  12. N. Ramatchandiran, S. Sumathi, and G. Buvaneswari, Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem., 48B, 865 (2009).

    CAS  Google Scholar 

  13. С. O. Kappe, Tetrahedron, 49, 6937 (1993).

    Article  CAS  Google Scholar 

  14. T. U. Mayer, T. M. Kapoor, S. J. Haggarty, R. W. King, S. L. Schreiber, and T. J. Mitchison, Science, 286, 971 (1999).

    Article  CAS  Google Scholar 

  15. D. S. Bose, R. K. Kumar, and L. Fatima, Synlett, 279 (2004).

  16. A. Dondoni, A. Massi, and S. Sabbatini, Tetrahedron Lett., 43, 5913 (2002).

    Article  CAS  Google Scholar 

  17. R. Elderfield, Heterocyclic compounds [Russian translation], Vol. 2, Izd-vo Inostr. Lit., Moscow (1954), p. 437.

    Google Scholar 

  18. R. Rehani, A. C. Shah, and V. P. Arya, Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem., 33B, 775 (1994).

    CAS  Google Scholar 

  19. O. V. Zaremba, S. N. Kovalenko, V. M. Nikitchenko, and T. A. Kondrachuk, in: V. G. Kartsev (editor), Chemistry and Biological Activity of Synthetic and Natural Compounds [in Russian], Vol. 2, IBS PRESS, Moscow (2003), p. 93.

    Google Scholar 

  20. M. M. Kurbanova, Russ. J. Org. Chem., 46, 599 (2010). [Zh. Org. Khim., 46, 606 (2010).]

    Article  CAS  Google Scholar 

  21. Q. Cheng, Q. Wang, T. Tan, N. Chen, and M. Shuai, J. Heterocycl. Chem., 49, 1352 (2012).

    Article  CAS  Google Scholar 

  22. M. A. Kolosov, V. D. Orlov, and Yu. M. Vasil’eva, Visn. Kharkiv. Nats. Un-ta. Khimiya, 731, 69 (2006).

    CAS  Google Scholar 

  23. M. A. Kolosov and V. D. Orlov, Chem. Heterocycl. Compd., 41, 260 (2005). [Khim. Geterotsikl. Soedin., 292 (2005).]

    Article  CAS  Google Scholar 

  24. I. V. Kulakov, D. M. Turdybekov, O. A. Nurkenov, G. M. Issabaeva, A. S. Makhmutova, K. M. Turdybekov, and S. D. Fazylov, Chem. Heterocycl. Compd., 45, 1117 (2009). [Khim. Geterotsikl. Soedin., 1395 (2009).]

    Article  CAS  Google Scholar 

  25. I. V. Kulakov, Chem. Heterocycl. Compd., 45, 1019 (2009). [Khim. Geterotsikl. Soedin., 1274 (2009).]

    Article  CAS  Google Scholar 

  26. F. H. Allen, O. Kennard, D. G. Watson, L. Brammer, A. G. Orpen, and R. Taylor, J. Chem. Soc., Perkin Trans. 2, S1 (1987).

  27. T. V. Rybalova, V. F. Sedova, Yu. V. Gatilov, and O. P. Shkurko, J. Struct. Chem., 43, 539 (2002). [Zh. Struktur. Khim., 43, 580 (2002).]

    Article  CAS  Google Scholar 

  28. I. V. Kulakov, O. S. Nikitina, A. S. Fisyuk, D. S. Goncharov, Z. T. Shul’gau, and A. E. Gulyaev, Chem. Heterocycl. Compd., 50, 670 (2014). [Khim. Geterotsikl. Soedin., 729 (2014).]

    Article  CAS  Google Scholar 

  29. CrysAlisPro, Oxford Diffraction (2007). Version 1.171.33.40.

  30. G. M. Sheldrick, Acta Crystallogr., Sect. A: Found. Crystallogr., A46, 467 (1990).

    Article  CAS  Google Scholar 

  31. G. M. Sheldrick, SHELXL-97. Program for the Refinement of Crystal Structures. University of Göttingen (1997).

  32. XP. Molecular Graphics Program. Version 5.03, Siemens Analytical X-Ray Instruments, Inc., Madison (1994).

  33. M. C. Burla, M. Camalli, B. Carrozzini, G. L. Cascarano, C. Giacovazzo, G. Polidori, and R. Spagna, SIR2002: the program, J. Appl. Crystallogr., 36, pt. 4, 1103 (2003).

  34. N. J. Miller, C. Rice-Evans, M. J. Davies, V. Gopinathan, and A. Milner, Clin. Sci., 84, 407 (1993).

    CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Omsk F. M. Dostoevskii State University, 55а Mira Ave., Omsk, 644077, Russia

    I. V. Kulakov

  2. Institute of Bioorganic Chemistry, 83 Mirzo Ulug’bek St., Tashkent, 100125, Uzbekistan

    S. A. Talipov

  3. Center for Life Sciences, Inc., 53 Kabanbay batyra Ave., Astana, 010000, Kazakhstan

    Z. T. Shulgau

  4. Sh. Ualikhanov Kokshetau State University, 76 Abay St., Kokshetau, 020000, Kazakhstan

    T. M. Seilkhanov

Authors
  1. I. V. Kulakov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. S. A. Talipov
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Z. T. Shulgau
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. T. M. Seilkhanov
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to I. V. Kulakov.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1604-1613, October, 2014.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Kulakov, I.V., Talipov, S.A., Shulgau, Z.T. et al. Synthesis, Structure, and Antiradical Activity of New Methano[1,3]Thiazolo[2,3-d][1,3,5]Benzoxa-Diazocine Derivatives. Chem Heterocycl Comp 50, 1478–1486 (2015). https://doi.org/10.1007/s10593-014-1613-1

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-014-1613-1

Keywords

Search

Navigation