Issue

Vol. 28 No. 7 (2016): Vol 28 Issue 7

Copyright (c) 2016 AJC

Creative Commons License

This work is licensed under a Creative Commons Attribution 4.0 International License.

Synthesis, Characterization and Antibacterial Activity of Novel Schiff Bases

https://doi.org/10.14233/ajchem.2016.19768
Pandiri Sreedhar
Department of Chemistry, Osmania University, Hyderabad-500 007, India
Gudipati Srinivas
Department of Chemistry, Osmania University, Hyderabad-500 007, India
Rallabandi Madhusudan Raju
Department of Chemistry, Osmania University, Hyderabad-500 007, India

Corresponding Author(s) : Rallabandi Madhusudan Raju

madhusudanraju2015@gmail.com

Asian Journal of Chemistry, Vol. 28 No. 7 (2016): Vol 28 Issue 7

Abstract

The present work describes the synthesis of novel Schiff bases (8.1-8.9) in five steps from diethyl oxalate and acetone as starting materials. Condensation of ethyl 1-(2-aminophenyl)-5-methyl-1H-pyrazole-3-carboxylate (6) with aromatic and heteroaromatic aldehydes (7.1-7.9) in presence of sodium sulphate at 50 °C in ethanol gave the corresponding imine derivatives (8.1-8.9) in quantitative yields. The structure of these compounds was determined by 1H NMR, mass and IR spectral data. These Schiff’s bases were further evaluated for antibacterial activity against the selected Gram-positive and Gram-negative bacteria pathogens. The antibacterial activity data revealed that Schiff base embedded with heteroaromatic ring was found to exhibit good antibacterial activity than the aromatic ring.

Keywords

Acetone Antibacterial activity Diethyl oxalate Schiff base Synthesis
Sreedhar, P., Srinivas, G., & Raju, R. M. (2016). Synthesis, Characterization and Antibacterial Activity of Novel Schiff Bases. Asian Journal of Chemistry, 28(7), 1603–1606. https://doi.org/10.14233/ajchem.2016.19768
Download Citation
Endnote/Zotero/Mendeley (RIS)
BibTeX
References
  1. H. Schiff, Justus Liebigs Ann. Chem., 131, 118 (1864); doi:10.1002/jlac.18641310113.
  2. H. Schiff, Justus Liebigs Ann. Chem., 140, 92 (1866); doi:10.1002/jlac.18661400106.
  3. S. Patai, The Chemistry of the Carbon-Nitrogen Double Bond, Wiley: New York, NY, USA (1970).
  4. G. Tennant, in ed.: I.O. Sutherland, Comprehensive Organic Chemistry, Pergamon: Oxford, UK, vol. 2, pp. 385–590 (1979).
  5. J.K. Whitesell, in ed.: E. Winterfeldt, Comprehensive Organic Synthesis, Pergamon: Oxford, UK, vol. 6, pp. 703-732 (1991).
  6. G.M. Robertson, in eds.: A.R. Katritzky, O. Meth-Cohn and C.W. Rees, Imines and their N-Substituted Derivatives, NH, NR and N-haloimines; In: Comprehensive Organic Functional Group Transformations, Elsevier: Amsterdam, The Netherlands, edn 1, vol. 3, pp. 403-423 (1995).
  7. S. Pawlenko, in eds.: D. Klamann and H. Hagemann Methoden der Organische Chemie (Houben-Weyl), Thieme: Stuttgart, Germany, vol. E14b, Part 1, pp. 222–281 (1980) (in German).
  8. R.H. Holm, J.G.W. Everett Jr and A. Chakravorty, Prog. Inorg. Chem., 7, 83 (1966); doi:10.1002/9780470166086.ch3.
  9. P. Vigato and S. Tamburini, Coord. Chem. Rev., 248, 1717 (2004); doi:10.1016/j.cct.2003.09.003.
  10. U. Schiff, Palermo. II, 1–59 (1867).
  11. A.P. Dobbs and S. Rossiter, in eds.: R.K. Alan and R.J. Taylor, Imines and their N-Substituted Derivatives: NH, NR, and N-Haloimines, In: Comprehensive Organic Functional Group Transformations II; Elsevier: Oxford, UK, pp. 419–450 (2005).
  12. G. Bringmann, M. Dreyer, J.H. Faber, P.W. Dalsgaard, J.W. Jaroszewski, H. Ndangalasi, F. Mbago, R. Brun and S.B. Christensen, J. Nat. Prod., 67, 743 (2004); doi:10.1021/np0340549.
  13. Z. Guo, R. Xing, S. Liu, Z. Zhong, X. Ji, L. Wang and P. Li, Carbohydr. Res., 342, 1329 (2007); doi:10.1016/j.carres.2007.04.006.
  14. M.M. Ali, M. Jesmin, M.K. Islam and M.A.K. Azad, Med. J. Isl. W. Acad. Sci., 21, 47 (2013).
  15. S.N. Pandeya, D. Sriram, G. Nath and E. De Clercq, Eur. J. Pharm., 9, 25 (1999); doi:10.1016/S0928-0987(99)00038-X.
  16. M.R. Islam, A.H. Mirza, Q.M.N. Huda and B.R. Khan, J. Bang. Chem. Soc., 2, 87 (1989).
  17. C. Shipman Jr, S.H. Smith, J.C. Drach and D.L. Klayman, Antiviral Res., 6, 197 (1986); doi:10.1016/0166-3542(86)90002-1.
  18. Y. Li, Z.-S. Yang, H. Zhang, B.-J. Cao, F.-D. Wang, Y. Zhang, Y.-L. Shi, J.-D. Yang and B.-A. Wu, Bioorg. Med. Chem., 11, 4363 (2003); doi:10.1016/S0968-0896(03)00499-1.
  19. M.N. Islam, S.M.S. Shahriar, M.K. Islam, M. Jesmin, M.M. Ali and J.A. Khanam, Int. Lett. Chem. Phys. Astron., 10, 12 (2013); doi:10.18052/www.scipress.com/ILCPA.10.12.
  20. B. Prabhakaran, N. Santhi and M. Emayavaramban, Int. Lett. Chem. Phys. Astron., 8, 53 (2013); doi:10.18052/www.scipress.com/ILCPA.8.53.
  21. S.B. Desai, P.B. Desai and K.R. Desai, Heterocycl. Commun., 7, 83 (2001); doi:10.1515/HC.2001.7.1.83.
  22. P. Przybylski, A. Huczynski, K. Pyta, B. Brzezinski and F. Bartl, Curr. Org. Chem., 13, 124 (2009); doi:10.2174/138527209787193774.
  23. A.A. Abdel Aziz, A.N.M. Salem, M.A. Sayed and M.M. Aboaly, J. Mol. Struct., 1010, 130 (2012); doi:10.1016/j.molstruc.2011.11.043.
  24. D. Sinha, A.K. Tiwari, S. Singh, G. Shukla, P. Mishra, H. Chandra and A.K. Mishra, Eur. J. Med. Chem., 43, 160 (2008); doi:10.1016/j.ejmech.2007.03.022.
  25. N. Vukovic, S. Sukdolak, S. Solujic and N. Niciforovic, Food Chem., 120, 1011 (2010); doi:10.1016/j.foodchem.2009.11.040.
  26. M.J. Pelczar Jr, R.D. Reid and E.C.S. Chan, Cultivation of Bacteria, In: Microbiology, Tata McGraw Hill Publishing Co. Ltd., New Delhi edn 4, p. 103 (1982).
  27. B.P. Nariya, R.N. Bhalodia, V.J. Shukla and B.M. Nariya, Int. J. Pharm. Technol. Res., 2, 2522 (2010).
Read More
Author biographies is not available.
Download
PDF
Statistic
Read Counter : 0 Download : 0