Skip to main content
SpringerLink
Log in

Synthesis of furyl-, furylvinyl-, thienyl-, pyrrolinylquinazolines and isoindolo[2,1-a]quinazolines

  • Full Articles
  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

A method for the synthesis of hydrogenated furyl-, furylvinyl-, thienyl-, and pyrrolinyl-substituted quinazolin-4-ones was developed. A possibility of the reaction of 2-furylquinazolines with maleic anhydride was demonstrated. A number of quinazolines obtained were subjected to a primary bioscreening on inhibition of acetylcholinesterase.

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

Similar content being viewed by others

References

  1. A. Padwa, C. S. Straub, J. Org. Chem., 2003, 68, 227.

    Article  CAS  Google Scholar 

  2. F. I. Zubkov, J. D. Ershova, A. A. Orlova, V. P. Zaytsev, E. V. Nikitina, A. S. Peregudov, A. V. Gurbanov, R. S. Borisov, V. N. Khrustalev, A. M. Maharramov, A. V. Varlamov, Tetrahedron, 2009, 65, 3789.

    Article  CAS  Google Scholar 

  3. F. I. Zubkov, V. P. Zaitsev, A. M. Piskareva, M. N. Eliseeva, E. V. Nikitina, N. M. Mikhailova, A. V. Varlamov, Russ. J. Org. Chem. (Engl. Transl.), 2010, 46, 1192 [Zh. Org. Khim., 2010, 46, 1191].

    Article  CAS  Google Scholar 

  4. F. I. Zubkov, V. P. Zaytsev, E. V. Nikitina, V. N. Khrustalev, S. V. Gozun, E. V. Boltukhina, A. V. Varlamov, Tetrahedron, 2011, 67, 9148.

    Article  CAS  Google Scholar 

  5. F. I. Zubkov, I. K. Airiyan, J. D. Ershova, T. R. Galeev, V. P. Zaytsev, E. V. Nikitina, A. V. Varlamov, RSC Advances, 2012, 2, 4103.

    Article  CAS  Google Scholar 

  6. V. P. Zaytsev, F. I. Zubkov, F. A. A. Toze, D. N. Orlova, M. N. Eliseeva, D. G. Grudinin, E. V. Nikitina, A. V. Varlamov, J. Heterocycl. Chem., 2013, 50 (S1), E18.

    Google Scholar 

  7. F. I. Zubkov, E. V. Nikitina, T. R. Galeev, V. P. Zaytsev, V. N. Khrustalev, R. A. Novikov, D. N. Orlova, A. V. Varlamov, Tetrahedron, 2014, 70, 1659.

    Article  CAS  Google Scholar 

  8. F. I. Zubkov, V. P. Zaitsev, A. S. Peregudov, N. M. Mikhailova, A. V. Varlamov, Russ. Chem. Bull. (Int. Ed.), 2007, 56, 1063 [Izv. Akad. Nauk, Ser. Khim., 2007, 1023].

    Article  CAS  Google Scholar 

  9. F. I. Zubkov, V. P. Zaytsev, E. V. Nikitina, R. S. Borisov, I. K. Airiyan, K. F. Turchin, A. V. Varlamov, Chem. Heterocycl. Compd. (Engl. Transl.), 2008, 44, 886 [Khim. Geterotsikl. Soedin., 2008, 1101].

    Article  CAS  Google Scholar 

  10. F. I. Zubkov, I. K. Airiyan, K. F. Turchin, V. P. Zaytsev, A. V. Gurbanov, A. M. Maharramov, V. N. Khrustalev, A. S. Peregudov, E. V. Nikitina, A. V. Varlamov, Synthesis, 2009, 4235.

    Google Scholar 

  11. F. I. Zubkov, I. K. Airiyan, A. A. Dzyubenko, N. I. Yudina, V. P. Zaytsev, E. V. Nikitina, A. V. Varlamov, V. N. Khrustalev, D. G. Grudinin, J. Heterocycl. Chem., 2010, 47, 400.

    CAS  Google Scholar 

  12. F. I. Zubkov, T. R. Galeev, E. V. Nikitina, I. V. Lazenkova, V. P. Zaytsev, A. V. Varlamov, Synlett, 2010, 14, 2063.

    Article  CAS  Google Scholar 

  13. P. Friedländer, N. Rosechdestwensky, Ber., 1915, 48, 1841.

    Article  Google Scholar 

  14. G. Honda, M. Tabata, Planta Med., 1978, 36, 85.

    Article  Google Scholar 

  15. Z.-Z. Ma, Y. Hano, T. Nomura, Y.-J. Chen, Heterocycles, 1997, 46, 541.

    Article  CAS  Google Scholar 

  16. Z.-Z. Ma, Y. Hano, T. Nomura, Y.-J. Chen, Heterocycles, 1999, 51, 1883.

    Article  CAS  Google Scholar 

  17. Z.-Z. Ma, Y. Hano, T. Nomura, Y.-J. Chen, Tennen Yuki Kagobutsu Toronkai Koen Yoshishu, 1999, 41, 547; Chem. Abstr., 2000, 132, 234276.

    Google Scholar 

  18. Z.-Z. Ma, Y. Hano, T. Nomura, Y.-J. Chen, Phytochemistry, 2000, 53, 1075.

    Article  CAS  Google Scholar 

  19. A. Cagir, S. H. Jones, R. Gao, B. M. Eisenhauer, S. M. Hecht, J. Am. Chem. Soc., 2003, 125, 13628.

    Article  CAS  Google Scholar 

  20. Z.-Z. Ma, Y. Hano, T. Nomura, Y.-J. Chen, Bioorg. Med. Chem. Lett., 2004, 14, 1193.

    Article  CAS  Google Scholar 

  21. S. B. Mhaske, N. P. Argade, J. Org. Chem., 2004, 69, 4563.

    Article  CAS  Google Scholar 

  22. T. Harayama, A. Hori, G. Serban, Y. Morikami, T. Matsumoto, H. Abe, Y. Takeuchi, Tetrahedron, 2004, 60, 10645.

    Article  CAS  Google Scholar 

  23. S. Eguchi, Top. Heterocycl. Chem., 2006, 6, 113.

    Article  CAS  Google Scholar 

  24. J. P. Michael, Nat. Prod. Rep., 2007, 24, 223.

    Article  CAS  Google Scholar 

  25. W. J. Houlihan, US Pat. 3509147.

  26. K. Pfeffer, Cytokine Growth Factor Rev., 2003, 14, 185.

    Article  CAS  Google Scholar 

  27. K. V. Parsa, L. P. Ganesan, M. V. Rajaram, M. A. Gavrilin, A. Balagopal, N. P. Mohapatra, M. D. Wewers, L. S. Schlesinger, J. S. Gunn, S. Tridandapani, PLoS Pathog., 2006, 2, e71.

    Article  CAS  Google Scholar 

  28. K. S. Kumar, P. M. Kumar, K. A. Kumar, M. Sreenivasulu, A. A. Jafar, D. Rambabu, G. R. Krishna, C. M. Reddy, R. Kapavarapu, K. Shivakumar, K. K. Priya, K. V. L. Parsa, M. Pal, Chem. Commun., 2011, 47, 5010.

    Article  CAS  Google Scholar 

  29. H. Gurien, B. B. Brown, J. Pharm. Sci., 1963, 52, 1102.

    Article  CAS  Google Scholar 

  30. R. J. Alaimo, C. J. Hatton, J. Med. Chem., 1972, 15, 108.

    Article  CAS  Google Scholar 

  31. T. Hisano, M. Ichikawa, A. Nakagawa, M. Tsuji, Chem. Pharm. Bull., 1975, 23, 1910.

    Article  CAS  Google Scholar 

  32. M. Yamato, J. Horiuchi, Y. Takeuchi, Chem. Pharm. Bull., 1981, 29, 3124.

    Article  CAS  Google Scholar 

  33. O. L. Vizgunova, Yu. V. Kozhevnikov, L. M. Obvintseva, V. S. Zalesov, Pharm. Chem. J., 1986, 20, 614.

    Article  Google Scholar 

  34. S.-W. Li, R. A. Batey, Chem. Commun., 2007, 36, 3759.

    Article  CAS  Google Scholar 

  35. Q.-L. Wang, H. Zhang, Y.-B. Jiang, Tetrahedron Lett., 2009, 50, 29.

    Article  CAS  Google Scholar 

  36. D. Ramesh, T. S. Reddy, M. Narasimhulu, S. Rajaram, N. Suryakiran, K. Ch. Mahesh, Y. Venkateswarlu, Chem. Lett., 38, 2009, 586.

    Google Scholar 

  37. A. Procopio, P. Costanzo, M. Curini, M. Nardi, M. Oliverio, G. Sindona, ACS Sustainable Chem. Eng., 2013, 1, 541.

    Article  CAS  Google Scholar 

  38. M. C. Gershengorn, S. Neumann, B. M. Raaka, C. J. Thomas, J. Inglese, N. T. Southall, S. Titus, W. Zheng, W. Huang, G. Krause, G. Kleinau, WO 2010047674 A1.

  39. V. P. Zaytsev, F. I. Zubkov, E. L. Motorygina, M. G. Gorbacheva, E. V. Nikitina, A. V. Varlamov, Chem. Heterocycl. Compd. (Engl. Transl.), 2012, 47, 1603 [Khim. Geterotsikl. Soedin., 2011, 1909].

    Article  CAS  Google Scholar 

  40. M. Fadaeinasab, A. Hamid, A. Hadi, Y. Kia, A. Basiri, V. Murugaiyah, Molecules, 2013, 18, 3779.

    Article  CAS  Google Scholar 

  41. L. H. Yale, M. Kalkstein, J. Med. Chem., 1967, 10, 334.

    Article  CAS  Google Scholar 

  42. B. V. Subba Reddy, A. Venkateswarlu, Ch. Madan, A. Vinu, Tetrahedron Lett., 2011, 52, 1891.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Peoples´ Friendship University of Russia, 6 ul. Miklukho-Maklaya, 117198, Moscow, Russian Federation

    V. P. Zaytsev, E. L. Revutskaya, M. G. Kuz´menko, F. I. Zubkov, E. A. Sorokina, E. V. Nikitina & A. V. Varlamov

  2. Shared Research and Educational Center of Physico-Chemical Studies of New Materials, Substances, and Catalytic Systems, 3 ul. Ordzhonikidze, 115419, Moscow, Russian Federation

    V. P. Zaytsev

  3. V. A. Engel´gardt Institute of Molecular Biology, Russian Academy of Sciences, 32 ul. Vavilova, 119991, Moscow, Russian Federation

    R. A. Novikov

  4. Department of Chemistry, University of Douala, Faculty of Sciences, PO Box 24157, Douala, Cameroon

    F. A. A. Toze

Authors
  1. V. P. Zaytsev
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. E. L. Revutskaya
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. M. G. Kuz´menko
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. R. A. Novikov
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. F. I. Zubkov
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. E. A. Sorokina
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. E. V. Nikitina
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. F. A. A. Toze
    View author publications

    You can also search for this author in PubMed Google Scholar

  9. A. V. Varlamov
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to V. P. Zaytsev.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 6, pp. 1345–1353, June, 2015.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Zaytsev, V.P., Revutskaya, E.L., Kuz´menko, M.G. et al. Synthesis of furyl-, furylvinyl-, thienyl-, pyrrolinylquinazolines and isoindolo[2,1-a]quinazolines. Russ Chem Bull 64, 1345–1353 (2015). https://doi.org/10.1007/s11172-015-1016-1

Download citation

  • Received:

  • Revised:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-015-1016-1

Key words

Search

Navigation