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Condition-controlled selective synthesis of hydroxyl(indolyl)- and bis(indolyl)barbiturates

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Abstract

By combining the structural features of indole and barbituric acid, new hybrid molecules were designed and synthesized. Hydroxy(indolyl)barbiturates and bis(indolyl)barbiturates were selectively prepared via the reaction of indoles with alloxan derivatives in various conditions.

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References

  1. B. Meunier, Acc. Chem. Res. 41, 69 (2008)

    Article  CAS  Google Scholar 

  2. C.A. Lipinski, F. Lombardo, B.W. Dominy, P.J. Feeney, Adv. Drug Deliv. Rev. 23, 3 (1997)

    Article  CAS  Google Scholar 

  3. R. Morphy, Z. Rankovic, J. Med. Chem. 48, 6523 (2005)

    Article  CAS  Google Scholar 

  4. G. Mehta, V. Singh, Chem. Soc. Rev. 31, 324 (2002)

    Article  CAS  Google Scholar 

  5. I. Chen, S. Safe, L. Bjeldanes, Biochem. Pharmacol. 51, 1069 (1996)

    Article  CAS  Google Scholar 

  6. S. Suzen, E. Buyukbingol, Il Farmaco 55, 246 (2000)

    Article  CAS  Google Scholar 

  7. E. Buyukbingol, S. Suzen, G. Klopman, Il Farmaco 49, 443 (1994)

    CAS  Google Scholar 

  8. S. Suzen, E. Buyukbingol, Il Farmaco 53, 525 (1998)

    Article  CAS  Google Scholar 

  9. P.M. Lieberman, A. Wolfler, P. Felsner, D. Hofer, K. Schauenstien, Int. Arch. Allergy Immunol. 112, 203 (1997)

    Article  Google Scholar 

  10. D. Page, H. Yang, W. Brown, C. Walpole, M. Fleurent, M. Fyfe, F. Gaudreault, S.S. Onge, Bioorg. Med. Chem. Lett. 22, 6183 (2007)

    Article  Google Scholar 

  11. Y.J. Chyan, B. Poeggler, R.A. Omar, D.G. Chain, B. Frangione, J. Ghiso, M.A. Pappolla, J. Biol. Chem. 274, 21937 (1999)

    Article  CAS  Google Scholar 

  12. I. Bolz, C. May, S. Spange, ARKIVOC iii, 60 (2007)

    Google Scholar 

  13. F. López-Munoz, R. Ucha-Udabe, C. Alamo, Neuropsychiatr. Dis. Treat. 1, 329 (2005)

    Google Scholar 

  14. R. Elayaraja, R.J. Karunakaran, Tetrahedron Lett. 53, 6901 (2012)

    Article  CAS  Google Scholar 

  15. Z. Shen, S. Ji, S. Wang, X. Zeng, Tetrahedron 61, 10552 (2005)

    Article  CAS  Google Scholar 

  16. D. Wang, J. Tang, Y. Zhou, M. Chen, C. Yu, Y. Duan, G. Jiang, Chem. Sci. 2, 803 (2011)

    Article  CAS  Google Scholar 

  17. M. Shiri, M.A. Zolfigol, H.G. Kruger, Z. Tanbakouchian, Chem. Rev. 110, 2250 (2010)

    Article  CAS  Google Scholar 

  18. S. Naskar, P. Paira, R. Paira, S. Mondal, A. Maity, A. Hazra, K.B. Sahu, P. Saha, S. Banerjee, P. Luger, M. Webe, N.B. Mondal, Tetrahedron 66, 5196 (2010)

    Article  CAS  Google Scholar 

  19. J. Yu, T. Shen, Y. Lin, Y. Zhou, Q. Song, Synth. Commun. 44, 2029 (2014)

    Article  CAS  Google Scholar 

  20. G. Srihari, M. Marthanda Murthy, Chem. Lett. 37, 268 (2008)

    Article  CAS  Google Scholar 

  21. M.B. Teimouri, B. Asnaashari, Tetrahedron Lett. 55, 2249 (2014)

    Article  CAS  Google Scholar 

  22. M.B. Teimouri, P. Akbari-Moghaddam, M. Motaghinezhad, Tetrahedron 69, 6804 (2013)

    Article  CAS  Google Scholar 

  23. R.J. Sundberg, Top. Heterocycl. Chem. 26, 47 (2010)

    CAS  Google Scholar 

Download references

Acknowledgement

The authors thank Kharazmi University Research Council for financial support of this research.

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Authors and Affiliations

  1. Faculty of Chemistry, Kharazmi University, Mofateh Ave., Tehran, Iran

    Mohammad Bagher Teimouri & Masoume Rezaei

Authors
  1. Mohammad Bagher Teimouri
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  2. Masoume Rezaei
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Correspondence to Mohammad Bagher Teimouri.

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Teimouri, M.B., Rezaei, M. Condition-controlled selective synthesis of hydroxyl(indolyl)- and bis(indolyl)barbiturates. J IRAN CHEM SOC 14, 1243–1251 (2017). https://doi.org/10.1007/s13738-017-1075-3

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  • DOI: https://doi.org/10.1007/s13738-017-1075-3

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