Skip to main content
Log in

Regioselective synthesis and biological evaluation of novel bis(2-chloroquinolines)

  • Published:
Research on Chemical Intermediates Aims and scope Submit manuscript

Abstract

Reaction of substituted 2,4-dichloroquinolines with bisphenol A in the presence of K2CO3 leads to novel bis(2-chloroquinolines) with high regioselectivity. All the synthesized compounds were characterized by use of spectral data. Preliminary evaluation of in-vitro antibacterial activity against a variety of Gram-positive and Gram-negative organisms was also conducted.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1
Scheme 2

Similar content being viewed by others

References

  1. N. Campbell, vol IVF, 231, (Elsevier, Amsterdam, 1976), p. 231

  2. R.D. Larsen, E.G. Corley, A.O. King, J.D. Carrol, P. Davis, T.R. Verhoeven, P.J. Reider, M. Labelle, J.Y. Gauthier, Y.B. Xiang, R.J. Zamboni, J. Org. Chem. 61, 3398 (1996)

    Article  CAS  Google Scholar 

  3. G. Roma, M.D. Braccio, G. Grossi, F. Mattioli, M. Ghia, Eur. J. Med. Chem. 35, 1021 (2000)

    Article  CAS  Google Scholar 

  4. Y.L. Chen, K.C. Fang, J.Y. Sheu, S.L. Hsu, C.C. Tzeng, J. Med. Chem. 44, 2374 (2001)

    Article  CAS  Google Scholar 

  5. C.C. Price, R.M. Roberts, J. Am. Chem. Soc. 68, 1255 (1946)

    Article  CAS  Google Scholar 

  6. D. Dube, M. Blouin, C. Brideau, C. Chan, S. Desmarais, D. Ethier, J.P. Falgueyret, R.W. Friesen, M. Girard, Y. Girard, J. Guay, P. Tagari, R.N. Young, Biorg. Med. Chem. Lett. 8, 1255 (1998)

    Article  CAS  Google Scholar 

  7. B. Kalluraya, S. Sreevinasa, Il Farmaco. 53, 399 (1998)

    Article  CAS  Google Scholar 

  8. M.P. Maguire, K.R. Sheets, K. Mc Vety, A.P. Spada, A. Zilberstein, J. Med. Chem. 37, 2129 (1994)

    Article  CAS  Google Scholar 

  9. M.G. Klug, P.M. Riehen, W.M. Aesch, W.N. Hagenthal le Bas, M.H.N. Grenzach-Wyhlen, P.P. Schwoben, J.P. Knoeringue, Quinoline derivatives., U.S. Patent 7166589, Jan 2007

  10. R. Sharon, P. Jean-Marie, J.W. Philip, J. Keith, Bioorg. Med. Chem. Lett. 15, 4806 (2005)

    Article  Google Scholar 

  11. M. Ernst, S. Wolfgang, O. Gunter, H. Barbara, L. Hans, K. Gerhand, Eur. J. Med. Chem. 25, 137 (1990)

    Article  Google Scholar 

  12. J.A. Brotons, M.F. Olea-Serrano, M. Villalobos, V. Pedraza, N. Olea, Environ. Health Perspect. 103(6), 608 (1995)

    Article  CAS  Google Scholar 

  13. P.L. Palanza, K.L. Howdeshell, S. Parmigiani, F.S. Yom Saal, Environ. Health Perspect. 110(suppl.3), 415 (2002)

    Article  CAS  Google Scholar 

  14. M. Alzbeta, K. Jaroslav, F. Maria, S. Sona, Mol. Cell. Endocrinol. 244, 57 (2005)

    Article  Google Scholar 

  15. Z. Wei, L. Jiayin, L. Lianming, H. Suping, L. Jinyong, Mol. Cell. Endocrinol. 283, 12 (2008)

    Article  Google Scholar 

  16. K. Miyoko, O. Reiko, Y. Kazutoshi, N. Masahisa, M. Gilberto, M. Alberta, K. Sakae, Gen. Comp. Endocrinol. 155, 574 (2008)

    Article  Google Scholar 

  17. S. Sarveswari, V. Vijayakumar, J. Chin. Chem. Soc. 8, 44 (2011)

    Google Scholar 

  18. S. Sarveswari S and V. Vijayakumar, Arabian J. Chem. 2011, doi:10.1016/j.arabjc.2011.01.032

  19. W.S. Loh, H.K. Fun, S. Sarveswari, V. Vijayakumar, B. Palakshi Reddy, Acta Cryst. E 66, o91 (2010)

    Article  CAS  Google Scholar 

  20. G. L. Balaji, K. Rajesh, Shabana Kouser ali, and V. Vijayakumar, Res. Chem. Intermed. 2012, doi: 10.1007/s11164-012-0715-6

  21. A. Farhanullah, S.Y. Kim, Y. Eun-Jeong, C. Eung-Chil, K. Sunghoon, T. Kang, S. Farhana, P. Sadhna, J. Leea, Bioorg. Med. Chem. 14, 7154 (2006)

    Article  CAS  Google Scholar 

  22. S. Rossiter, P. Jean-Marie, P.J. Whitfield, K. Jones, Bioorg. Med. Chem. Lett. 15, 4806 (2005)

    Article  CAS  Google Scholar 

  23. K. Rajesh, B. Palakshi Reddy, V. Vijayakumar, Indian J. Het. Chem. 19, 95 (2009)

    CAS  Google Scholar 

  24. M. M. Ismail, M. Abass, M. M. Hassan, 4th International electronic conference on synthetic organic chemistry (ECSOC-4), www.mdpi.org/ecsoc-4.htm, 1–30 Sept 2000

  25. Z. Yang, R. Fathi, Q. Zhu, H-J. Cho, Y. Liu, A. Sanddrasagra, C. R. Wobbe, U.S. Patent 20090054477 A1, (2009)

  26. S. Natarajan, K. Rajesh, V. Vijayakumar, J. Suresh, P.L. Nilantha Lakshman, Acta Cryst. E 65, o671 (2009)

    Article  CAS  Google Scholar 

  27. M.E. Belli, G. Illuminate, G. Marino, Tetrahedron 19, 345 (1963)

    Article  CAS  Google Scholar 

  28. G.R. Newkome, W.W. Paudler, Contemporary heterocyclic chemistry (Wiley, New York, 1982)

    Google Scholar 

  29. S. Goto, K. Jo, T. Kawakita, S. Mitsuhashi, T. Nishino, N. Ohsawa, H. Tanami, Chemother. 29, 76 (1981)

    Google Scholar 

Download references

Acknowledgments

We are grateful for financial support from the Department of Science and Technology, Government of India (grant no. SR/FTP/CS-108/2006) and to VIT University, Vellore, for providing research facilities.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to V. Vijayakumar.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOC 6706 kb)

Rights and permissions

Reprints and permissions

About this article

Cite this article

Rajesh, K., Palakshi Reddy, B., Sarveswari, S. et al. Regioselective synthesis and biological evaluation of novel bis(2-chloroquinolines). Res Chem Intermed 39, 4259–4267 (2013). https://doi.org/10.1007/s11164-012-0942-x

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-012-0942-x

Keywords

Navigation