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Practical one-pot synthesis of semicarbazone derivatives via semicarbazide, and evaluation of their antibacterial activity

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Abstract

New series of 2-(aryl or alkyl)-N-phenylhydrazine-1-carboxamides 1a–j were synthesized through one-pot reactions of aldehyde or ketones, hydrazine hydrate, and phenylisocyanate in MeOH. The structure of products was confirmed by Fourier transform infrared (FT-IR), proton nuclear magnetic resonance (1H NMR), and 13C NMR spectra. Minimum inhibitory concentration (MIC) of antibacterial activity of 1a–j was screened against five bacterial strains. Compound 1f showed antibacterial activity against Pseudomonas aeruginosa and Staphylococcus aureus.

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References

  1. S.N. Pandeya, P. Yogeeswari, J.P. Stables, Eur. J. Med. Chem. 35, 879 (2000)

    Article  CAS  Google Scholar 

  2. J.R. Dimmock, K.K. Sidhu, S.D. Tumber, S.K. Basran, M. Chen, J.W. Quail, J. Yang, I. Rozas, D.F. Weaver, Eur. J. Med. Chem. 30, 287 (1995)

    Article  CAS  Google Scholar 

  3. M. Santagati, M. Modica, A. Santagati, F. Russo, S. Spampinato, Pharmazie 51, 7 (1996)

    CAS  Google Scholar 

  4. T. Hemalatha, P.K.M. Imran, A. Gnanamani, S. Na-garajan, Nitric Oxide 19, 303 (2008)

    Article  CAS  Google Scholar 

  5. K. Alomar, V. Gaumet, M. Allain, G. Bouet, A. Lan-dreau, J. Inorg. Biochem. 115, 36 (2012)

    Article  CAS  Google Scholar 

  6. D.S. Raja, N.S.P. Bhuvanesh, K. Natarajan, Inorg. Chem. 50, 12852 (2011)

    Article  CAS  Google Scholar 

  7. L.T.S. Rocha, K.A. Costa, A.C.P. Oliveira, E.B. Nascimento, C.M. Bertollo, F. Araujo, L.R. Teixeira, S.P. Andrade, H. Beraldo, M.M. Coelho, Life Sci. 79, 499 (2006)

    Article  CAS  Google Scholar 

  8. S. Shukla, R.S. Srivastava, S.K. Shrivastava, A. Sodhi, P. Kumar, Asian Pac. J. Trop. Biomed. 2, 1040 (2012)

    Article  Google Scholar 

  9. S. Dutta, S. Padhye, K.I. Priyadarsini, C. Newton, Bioorg. Med. Chem. Lett. 15, 2738 (2005)

    Article  CAS  Google Scholar 

  10. R.B. de Oliveira, E.M. de Souza-Fagundes, R.P.P. Soares, A.A. Andrade, A.U. Krettli, C.L. Zani, Eur. J. Med. Chem. 43, 1983 (2008)

    Article  Google Scholar 

  11. H. Cerecetto, R. Di Maio, M. González, M. Risso, G. Sagrera, G. Seoane, A. Denicola, G. Peluffo, C. Quijano, A.O.M. Stoppani, M. Paulino, C. Olea-Azar, M.A. Basombrío, Eur. J. Med. Chem. 35, 343 (2000)

    Article  CAS  Google Scholar 

  12. C. Gan, J. Cui, S. Su, Q. Lin, L. Jia, L. Fan, Y. Huang, Steroids 87, 99 (2014)

    Article  CAS  Google Scholar 

  13. S. Vijaya Laxmi, B. Rajitha, Med. Chem. Res. 21, 85 (2012)

    Article  CAS  Google Scholar 

  14. E. Akoz, S. Erdemir, M. Yilmaz, J. Incl. Phenom. Macrocycl. Chem. 73, 449 (2012)

    Article  CAS  Google Scholar 

  15. C.M. Goulart, A. Esteves-Souza, C.A. Martinez-Huitle, C.J. Ferreira Rodrigues, M.A. Medeiros Maciel, A. Echevarria, Corros. Sci. 67, 281 (2013)

    Article  CAS  Google Scholar 

  16. K. Takagi, H. Hamaguchi, T. Nishimatsu, T. Konno, Vet. Parasitol. 150, 177 (2007)

    Article  CAS  Google Scholar 

  17. K. Alomar, V. Gaumet, M. Allain, G. Bouet, A. Landreau, J. Inorg. Biochem. 115, 36 (2012)

    Article  CAS  Google Scholar 

  18. P. Anitha, N. Chitrapriya, Y.J. Jang, P. Viswanathamurthi, J. Photochem. Photobiol. B 129, 17 (2013)

    Article  CAS  Google Scholar 

  19. É.A. Enyedy, G.M. Bognár, N.V. Nagy, T. Jakusch, T. Kiss, D. Gambino, Polyhedron 67, 242 (2014)

    Article  CAS  Google Scholar 

  20. Y. Li, Z.-Y. Yang, Z.-C. Liao, Z.-C. Han, Z.-C. Liu, Inorg. Chem. Commun. 13, 1213 (2010)

    Article  CAS  Google Scholar 

  21. H.L. Singh, J.B. Singh, K.P. Sharma, Res. Chem. Intermed. 38, 53 (2012)

    Article  CAS  Google Scholar 

  22. P.R. Verma, S. Mandal, P. Gupta, B. Mukhopadhyay, Tetrahedron Lett. 54, 4914 (2013)

    Article  CAS  Google Scholar 

  23. G. Sonia, T.K. Ravi, Med. Chem. Res. 22, 3428 (2013)

    Article  CAS  Google Scholar 

  24. M. Shalini, P. Yogeeswari, D. Sriram, J.P. Stables, Biomed. Pharmacother. 63, 187 (2009)

    Article  CAS  Google Scholar 

  25. N. Raghav, R. Kaur, Med. Chem. Res. 23, 4669 (2014)

    Article  CAS  Google Scholar 

  26. M.E. Jung, B.T. Chamberlain, C.-L.C. Ho, E.J. Gillespie, K.A. Bradley, A.C.S. Med, Chem. Lett. 5, 363 (2014)

    CAS  Google Scholar 

  27. C.S. Sharma, T. Verma, H.P. Singh, N. Kumar, Med. Chem. Res. 23, 4814 (2014)

    Article  CAS  Google Scholar 

  28. B. Qi, B. Mi, X. Zhai, Z. Xu, X. Zhang, Z. Tian, P. Gong, Bioorg. Med. Chem. 21, 5246 (2013)

    Article  CAS  Google Scholar 

  29. S. Jin Tan, H.-W. Xi, S. Bedoura, K.H. Lim, Inorg. Chim. Acta 29, 384 (2012)

    Google Scholar 

  30. K. Jakusová, M. Gáplovský, J. Donovalová, M. Cigáň, H. Stankovičová, R. Sokolík, J. Gašpar, A. Gáplovský, Chem. Pap. 67, 117 (2013)

    Article  Google Scholar 

  31. N.O. Mahmoodi, N. Safari, B. Sharifzadeh, Synth. Commun. 44, 245 (2014)

    Article  CAS  Google Scholar 

  32. N.O. Mahmoodi, I. Nikokar, M. Farhadi, A. Ghavidast, Z. Naturforsch. 69b, 715 (2014)

    Google Scholar 

  33. N.O. Mahmoodi, J. Parvizi, B. Sharifzadeh, M. Rassa, Arch. Pharm. Chem. Life Sci. 346, 1 (2013)

    Article  Google Scholar 

  34. N.O. Mahmoodi, B. Sharifzadeh, M. Mamaghani, K. Tabatabaeian, A. Salimi Chirani, I. Nikokar, Bioorg. Med. Chem. Lett. 23, 548 (2013)

    Article  Google Scholar 

  35. N.O. Mahmoodi, S. Shoja, B. Sharifzadeh, M. Rassa, Med. Chem. Res. 23, 1207 (2014)

    Article  CAS  Google Scholar 

  36. N.O. Mahmoodi, S. Ramzanpour, F. Ghanbari Pirbasti, Arch. Pharm. 348, 275 (2015)

  37. H. Kiyani, N.O. Mahmoodi, K. Tabatabaeian, M.A. Zanjanchi, J. Phys. Org. Chem. 22, 559 (2009)

    Article  CAS  Google Scholar 

  38. N.O. Mahmoodi, K. Tabatabaeian, A. Ghavidast. Chin. Chem. Lett. 21, 1199 (2010)

    Article  CAS  Google Scholar 

  39. N.O. Mahmoodi, A. Ghavidast, Chem. Heterocycl. Compd. 49, 1451 (2014)

    Article  CAS  Google Scholar 

  40. N.O. Mahmoodi, K. Tabatabaeian, H. Kiyani, Helv. Chim. Acta 95, 536 (2012)

    Article  CAS  Google Scholar 

  41. Z. Khodaee, A. Yahyazadeh, N.O. Mahmoodi, J. Het, Chemistry 50, 288 (2013)

    CAS  Google Scholar 

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Acknowledgments

The authors are grateful to the Research Council of University of Guilan for financial support of this work.

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Authors and Affiliations

  1. Department of Organic Chemistry, Faculty of Sciences, University of Guilan, PO Box 41335-1914, Rasht, Iran

    Nosrat O. Mahmoodi, Mojtaba Namroudi, Fateme Ghanbari Pirbasti & Hossein Roohi

  2. Laboratory of Microbiology and Immunology of Infectious Diseases, Paramedicine Faculty, Guilan University of Medical Sciences, PO Box 44715-1361, Guilan, Iran

    Iraj Nikokar

Authors
  1. Nosrat O. Mahmoodi
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  2. Mojtaba Namroudi
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  3. Fateme Ghanbari Pirbasti
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  4. Hossein Roohi
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Correspondence to Nosrat O. Mahmoodi.

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Mahmoodi, N.O., Namroudi, M., Ghanbari Pirbasti, F. et al. Practical one-pot synthesis of semicarbazone derivatives via semicarbazide, and evaluation of their antibacterial activity. Res Chem Intermed 42, 3625–3636 (2016). https://doi.org/10.1007/s11164-015-2235-7

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