Skip to main content
SpringerLink
Log in

Synthesis, antibacterial and antitubercular activity of novel Schiff bases of 2-(1-benzofuran-2-yl)quinoline-4-carboxylic acid derivatives

  • Published:
Russian Journal of General Chemistry Aims and scope Submit manuscript

Abstract

Novel Schiff bases of 2-(1-benzofuran-2-yl)quinoline-4-carboxylic acid derivatives 5a–5e were synthesized by the reaction of 2-(1-benzofuran-2-yl)quinoline-4-carbohydrazide 3 with substituted aromatic aldehydes 4a–4e in presence of catalytic amount of acetic acid. Reaction of methyl 2-(1-benzofuran-2-yl)-quinoline-4-carboxylate 2 with hydrazine hydrate upon refluxing in ethanol for 4 h gave the key intermediate, hydrazide compound 3. All newly synthesized compounds were characterized by IR, NMR and Mass spectra and screened for antibacterial and antitubercular activity. Among the tested compounds carbohydrazide 3 and the compounds 5a and 5e exhibited high activity against S. aureus and E. faecalis respectively with MIC 0.064 mg/mL. Compound 5e demonstrated significant activity against S. aureus and E. faecalis with MIC 0.064 mg/mL. The antibacterial tests revealed hydrazide derivative 3 sensitivity at 25 μg/mL, showing high activity among the synthesized compounds.

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. Khanam, H. and Shamsuzzaman, Eur. J. Med. Chem., 2015, vol. 97, p. 483. doi org/10.1016/j.ejmech.2014.11.039

    Article  CAS  Google Scholar 

  2. Choi, M., Jo, H., Park, H.J., Sateesh Kumar, A., Lee, J., Yun, J., Kim, Y., Han, S., Jun, J.K., and Cho, J., Bioorg. Med. Chem. Lett., 2015 vol. 6, p. 2545. doi org/10.1016/j.bmcl.2015.04.050

    Google Scholar 

  3. Kenchappa, R., Bodke, Y.D., Asha, B., Sandeep Telkar, and Aruna, S.M., Med. Chem. Res., 2014, vol. 23, p. 3065. doi 10.1007/s00044-013-0892-x

    Article  CAS  Google Scholar 

  4. Kuntal, M. and Yadvendra, K.A., Med. Chem. Res., 2011, vol. 20, p. 300. doi 10.1007/s00044-010-9322-5

    Article  Google Scholar 

  5. Tejpal, S.C., Nutan, S., and Sunita, B., Med. Chem. Res., 2014, vol. 23, p. 1350. doi 10.1007/s00044-013-0735-9

    Article  Google Scholar 

  6. Kenchappa, R., Yadav, D.B., Peethambar, S.K., and Sandeep Telkar, Med. Chem. Res., 2013. vol. 22, p. 4787. doi 10.1007/s00044-013-0494-7

    Article  CAS  Google Scholar 

  7. Venkatesh, K.B., Yadav, D.B., and Biradar, S.A., Phosphorus, Sulfur, Silicon and the Related Elements, 2010, vol. 185, p. 1926. doi org/10.1080/10426500903376154

    Article  CAS  Google Scholar 

  8. Mohsen, A., Alireza, A., Ali, A., Mohammad, B., and Davood, N., Tetrahedron Lett., 2015, vol. 56, p. 2141. doi org/10.1016/j.tetlet.2015.03.049

    Article  Google Scholar 

  9. Chauhan, P.M.S. and Sanjay, K.S., Curr. Med. Chem., 2001, vol. 8, p. 1535. doi 10.2174/0929867013371851

    Article  CAS  Google Scholar 

  10. Palimkar, S.S. and Siddiqui, S.A., J. Org. Chem., 2003, vol. 68, p. 9371. doi 10.1021/jo035153u

    Article  CAS  Google Scholar 

  11. Lau, K.Y., Mayr, A., and Cheung, K.K., Inorg. Chim. Acta., 1999, vol. 285, p. 223. doi org/10.1016/S0020-1693(98)00352-1

    Article  CAS  Google Scholar 

  12. Raman, N., Muthuraj, V., Ravichandran, S., and Kulandaisamy, A., J. Chem. Sci., 2003, vol. 115, p. 161. doi 10.1007/BF02704255

    Article  CAS  Google Scholar 

  13. Sunita, B., Nutan, S., and Tejpal, S.C., J. Chem., 2012, vol. 2013, p. 4. doi org/10.1155/2013/909217

    Google Scholar 

  14. Piotr, P. and Bogumil, B., Biopolymer., 2002, vol. 67, p. 61. doi 10.1002/bip.10043

    Article  Google Scholar 

  15. Yogesh, K.V., Rathish, N., Mayur, S., and Shipra, B.A., J. Serb. Chem. Soc., 2004, vol. 69, no. 12, p. 991. doi 542.913+54.02:547.576+547.77

    Article  Google Scholar 

  16. Holla, B.S., Rao, B.S., Shridhara, K., and Akberali, P.M., Farmaco, 2000, vol. 55, p. 338. doi org/10.1016/S0014-827X(00)00033-1

    Article  CAS  Google Scholar 

  17. Capdeville, R., Buchdunger, E., Zimmermann, J., and Matter, A., Nat. Rev. Drug. Discov., 2002, vol. 1, p. 493. doi 10.1038/nrd839

    Article  CAS  Google Scholar 

  18. Kenchappa, R., Bodke, Y.D., Sandeep Telkar, Aruna, S.M., and Giridhar, M., Russ. J. Gen. Chem, 2016, vol. 86, no. 12, p. 2827. doi 10.1134/S107036321612046X

    Article  CAS  Google Scholar 

  19. Nasser, K.S.A.M., Eur. J. Med. Chem., 2010, vol. 45, p. 5265. doi org/10.1016/j.ejmech.2010.08.046

    Article  Google Scholar 

  20. Sander, T., Freyss, J., Von, K. M., Reich, J.R., and Rufener, C., J. Chem. Inf. Model., 2009, vol. 49, p. 232. doi 10.1021/ci800305f

    Article  CAS  Google Scholar 

  21. Hanwell, M.D., Curtis, D.E., Lonie, D.C., Vandermeersch, T., Zurek, E., and Hutchison, G.R., J. Cheminform., 2012, vol. 4, p. 17. doi 10.1186/1758-2946-4-17

    Article  CAS  Google Scholar 

  22. Trott, O. and Olson, A.J., J. Comput. Chem., 2010, vol. 31, p. 455. doi 10.1002/jcc.21334

    CAS  Google Scholar 

  23. Yang, J., Liu, Y., Bi, J., Cai, Q., Liao, X., and Li, W., Mol. Microbiol., 2015, vol. 95, p. 791. doi 10.1111/mmi.12892

    Article  CAS  Google Scholar 

  24. Vijesh, A.M., Isloor, A.M., Telkar, S., Arulmoli, T., and Fun, H.K., Arab. J. Chem., 2013, vol. 6, p. 197. doi org/10.1016/j.arabjc.2011.10.007

    Article  CAS  Google Scholar 

  25. Morris, M.M., Goodsell, D.S., Halliday, R.S., Huey, R., Hart, W.E., Belew, R.K., and Olson, A.J., J. Comput. Chem., 1998, vol. 19, p. 1639. doi 10.1002/(SICI)1096-987X(19981115)19:14<1639::AID-JCC10>3.0.CO;2-B

    Article  CAS  Google Scholar 

  26. Laskowski, R.A. and Swindells, M.B., J. Chem. Inf. Model., 2011, vol. 51, p. 2778. doi 10.1021/ci200227u.

    Article  CAS  Google Scholar 

  27. Delano, W.L., The PyMOL Molecular Graphics System, 2002, Version 1.5.0.4 Schrödinger, LLC, 1998. doi 10.1007/978-3-319-23603-2

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Post-Graduate Studies and Research in Industrial Chemistry, Jnana Sahyadri, Kuvempu University Shankaraghatta, Shivamogga, Karnataka, 577451, India

    Y. D. Bodke, S. Shankerrao & R. Kenchappa

  2. Department of Post-Graduate Studies and Research in Biotechnology and Bioinformatics, Jnana Sahyadri, Kuvempu University, Shankaraghatta, Karnataka, 577451, India

    S. Telkar

Authors
  1. Y. D. Bodke
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. S. Shankerrao
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. R. Kenchappa
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. S. Telkar
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Y. D. Bodke.

Additional information

The text was submitted by the authors in English.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Bodke, Y.D., Shankerrao, S., Kenchappa, R. et al. Synthesis, antibacterial and antitubercular activity of novel Schiff bases of 2-(1-benzofuran-2-yl)quinoline-4-carboxylic acid derivatives. Russ J Gen Chem 87, 1843–1849 (2017). https://doi.org/10.1134/S1070363217080321

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070363217080321

Keywords

Search

Navigation