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An efficient one pot–three component cyclocondensation in the synthesis of 2-(2-chloroquinolin-3-yl)-2,3-dihydroquinazolin-4(1H)-ones: potential antitumor agents

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Abstract

Montmorillonite K10 efficiently catalyzed a one pot–three component cyclocondensation of isatoic anhydride, NH4OAc and aromatic/heteroaromatic aldehydes under ambient conditions to produce the corresponding 2-substituted-2,3-dihydroquinazolin-4(1H)-ones in good yields. The 2-(2-chloroquinolin-3-yl)-2,3-dihydroquinazolin-4(1H)-ones 3a–d were screened for their antitumor activity against Ehrlich Ascites Carcinoma tumor cells

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References

  1. G. Gil, S.J. Brse, Comb. Chem. 11, 175 (2009)

    Article  CAS  Google Scholar 

  2. S.M. Roopan, F.N. Khan, ARKIVOC 13, 161 (2009)

    Google Scholar 

  3. S.M. Roopan, T. Maiyalagan, F.N. Khan, Can. J. Chem. 86, 1019 (2008)

    Article  CAS  Google Scholar 

  4. M. Kowalska, D.L. Cock, Chemosphere 36, 547 (1998)

    Article  CAS  Google Scholar 

  5. V.P. Evangetou, M. Marsi, M.M. Vandiviere, Plant Sol. 213, 63 (1999)

    Article  Google Scholar 

  6. O.Y. Kwon, K.W. Park, S.Y. Jeong, Bull. Korean Chem. Soc. 22, 678 (2001)

    CAS  Google Scholar 

  7. B.K.G. Theng, Dev. Sedimentol. 35, 197 (1982)

    CAS  Google Scholar 

  8. P. Komadel, J. Madejova, in Handbook of Clay Science: Development in Clay, vol. 1, ed. by F. Bergaya, B.K.G. Theng, G. Lagaly (Elsevier, Amsterdam, 2006), p. 263

    Google Scholar 

  9. C. Larksarp, H. Alper, J. Org. Chem. Rev. 65, 2773 (2000)

    Article  CAS  Google Scholar 

  10. V. Krchnak, M.W. Holladay, Chem. Rev. 102, 61 (2002)

    Article  CAS  Google Scholar 

  11. B.B. Tour, D.G. Hall, Chem. Rev. 109, 4439 (2009)

    Article  Google Scholar 

  12. S.M. Roopan, F.N. Khan, B.K. Mandal, Tetrahedron Lett. 51, 2309 (2010)

    Article  CAS  Google Scholar 

  13. S.S. Parmar, R. Kumar, J. Med. Chem. 11, 635 (1968)

    Article  CAS  Google Scholar 

  14. K.-I. Ozaki, Y. Yamada, T. Oine, T. Ishizuka, Y. Iwasawa, J. Med. Chem. 28, 568 (1985)

    Article  CAS  Google Scholar 

  15. A. Kamal, E.V. Bharathi, M.J. Ramaiah, D. Dastagiri, J.S. Reddy, A. Viswanath, F. Sultana, S.N.C.V.L. Pushpavalli, M. Pal-Bhadra, H.K. Srivastava, G.N. Sastry, A. Juvekar, S. Sen, S. Zingde, Bioorg. Med. Chem. 18, 526 (2010)

    Article  CAS  Google Scholar 

  16. M.S. Mohamed, M.M. Kamel, E.M.M. Kassem, N. Abotaleb, S.I.A. El-moez, M.F. Ahmed, Eur. J. Med. Chem. 45, 3311 (2010)

    Article  CAS  Google Scholar 

  17. J.A. Moore, G.J. Sutherland, R. Sowerby, E.G. Kelly, S. Palemo, W. Webster, J. Org. Chem. 887 (1969)

  18. W. Su, B. Yang, Aust. J. Chem. 55, 695 (2002)

    Article  CAS  Google Scholar 

  19. D. Shi, L. Rong, J. Wang, Q. Zhuang, X. Wang, H. Hu, Tetrahedron Lett. 44, 3199 (2003)

    Article  CAS  Google Scholar 

  20. D.Q. Shi, L.C. Rong, J.X. Wang, X.S. Wang, S.J. Tu, H.W. Hu, Chem. J. Chin. Univ. 25, 2051 (2004)

    Google Scholar 

  21. T.A.K. Smith, H. Stephen, Tetrahedron 1, 38 (1957)

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Acknowledgments

This work was supported by Department of Science & Technology Government of India (Grant No. SR/FTP/CS-99/2006). We also acknowledge SAIF, IIT Madras, Chennai for providing NMR and MS facility. The authors are grateful to the VIT University management for their generous support and facilities.

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Authors and Affiliations

  1. Organic & Medicinal Chemistry Research Laboratory, Organic Chemistry Division, School of Advanced Sciences, VIT University, Vellore , 632 014, Tamil Nadu, India

    Selvaraj Mohana Roopan & F. Nawaz Khan

  2. Division of High Technology Materials Research, Busan Center, Korea Basic Science Institute (KBSI), Busan, 618 230, Korea

    F. Nawaz Khan & Jong Sung Jin

  3. Swamy Vivekanandha College of Pharmacy, Elayampalayam, Tiruchengodu Taluk, Namakkal District, 637 205, Tamil Nadu, India

    R. Senthil Kumar

Authors
  1. Selvaraj Mohana Roopan
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  2. F. Nawaz Khan
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  3. Jong Sung Jin
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  4. R. Senthil Kumar
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Correspondence to F. Nawaz Khan.

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Roopan, S.M., Nawaz Khan, F., Jin, J.S. et al. An efficient one pot–three component cyclocondensation in the synthesis of 2-(2-chloroquinolin-3-yl)-2,3-dihydroquinazolin-4(1H)-ones: potential antitumor agents. Res Chem Intermed 37, 919–927 (2011). https://doi.org/10.1007/s11164-011-0301-3

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  • DOI: https://doi.org/10.1007/s11164-011-0301-3

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