Advertisement

Research on Chemical Intermediates

, Volume 42, Issue 8, pp 6531–6542 | Cite as

One-pot multicomponent synthesis of indol-3-yl-hydrazinyl thiazoles as antimicrobial agents

  • Nosrat O. MahmoodiEmail author
  • Behzad Khalili
  • Olia Rezaeianzade
  • Atefeh Ghavidast
Article

Abstract

A series of novel mono- and bis(indol-3-yl)hydrazinyl thiazole derivatives were efficiently synthesized via one-pot cyclocondensation of mono- or bis(indole-3-carbaldehyde), thiosemicarbazide, and phenacyl bromides. The structure of the products was confirmed by Fourier-transform infrared (FT-IR), 1H nuclear magnetic resonance (NMR), and 13C NMR spectra. All synthesized compounds were evaluated for in vitro antibacterial activity against Gram-positive (Bacillus subtilis and Micrococcus luteus) and Gram-negative bacteria (Pseudomonas aeruginosa and Salmonella enteritis). Among the compounds screened, a few were found to be highly effective antibacterial agents. The bis-compounds with OCH3 donating group exhibited good activity against the Gram-positive bacteria.

Keywords

Bisindole Thiazole Bisthiazole Vilsmeier reaction Antimicrobial 

Notes

Acknowledgments

This study was supported in part by the Research Committee of the University of Guilan.

Supplementary material

11164_2016_2478_MOESM1_ESM.docx (1.5 mb)
Supplementary material 1 (DOCX 1523 kb)

References

  1. 1.
    V. Sharma, P. Kumar, D. Pathak, J. Heterocycl. Chem. 47, 491 (2010)Google Scholar
  2. 2.
    N.K. Kaushik, N. Kaushik, P. Attri, N. Kumar, C.H. Kim, A.K. Verma, E.H. Choi, Molecules 18, 6620 (2013)CrossRefGoogle Scholar
  3. 3.
    M.Z. Zhang, Q. Chen, G.F. Yang. Eur. J. Med. Chem. 89, 421 (2015)CrossRefGoogle Scholar
  4. 4.
    R. Sakhuja, S.S. Panda, L. Khanna, Sh Khurana, S.C. Jain, Bioorg. Med. Chem. Lett. 21, 5465 (2011)CrossRefGoogle Scholar
  5. 5.
    Y.M.A. Hiari, A.M. Qaisi, M.M. Abadelah, W. Voelter, Monatsh. Chem. 137, 243 (2006)CrossRefGoogle Scholar
  6. 6.
    E. Yamuna, R.A. Kumar, M. Zeller, P.K. Rajendra, J. Eur. J. Med. Chem. 47, 228 (2012)CrossRefGoogle Scholar
  7. 7.
    B. Jiang, X.H. Gu, Bioorg. Med. Chem. 8, 363 (2000)CrossRefGoogle Scholar
  8. 8.
    D. Kumar, N.M. Kumar, B. Noel, K. Shah, Eur. J. Med. Chem. 55, 432 (2012)CrossRefGoogle Scholar
  9. 9.
    N. Nagesh, G. Raju, R. Srinivas, P. Ramesh, M. Damoder Reddy, C. Raji Reddy, Biochim. Biophys. Acta 1850, 129 (2015)CrossRefGoogle Scholar
  10. 10.
    Q. Guan, C. Han, D. Zuo, M. Zhai, Z.Q. Li, Q. Zhang, Y. Zhai, X. Jiang, K. Bao, Y. Wu, W. Zhang, Eur. J. Med. Chem. 87, 306 (2014)CrossRefGoogle Scholar
  11. 11.
    R. Breslow, J. Am. Chem. Soc. 80, 3719 (1958)CrossRefGoogle Scholar
  12. 12.
    F. Haviv, J.D. Ratajczyk, R.W. DeNet, F.A. Kerdesky, R.L. Walters, S.P. Schmidt, J.H. Holms, P.R. Young, G.W. Carter, J. Med. Chem. 31, 1719 (1988)CrossRefGoogle Scholar
  13. 13.
    W.C. Patt, H.W. Hamilton, M.D. Taylor, M.J. Ryan, D.G. Taylor Jr, C.J.C. Connolly, A.M. Doherty, S.R. Klutchko, I. Sircar, B.A. Steinbaugh, B.L. Batley, C.A. Painchaud, S.T. Rapundalo, B.M. Michniewicz, S.C. Olson, J. Med. Chem. 35, 2562 (1992)CrossRefGoogle Scholar
  14. 14.
    K. Tsuji, H. Ishikawa, Bioorg. Med. Chem. Lett. 4, 1601 (1994)CrossRefGoogle Scholar
  15. 15.
    F.W. Bell, A.S. Cantrell, M. Hoegberg, S.R. Jaskunas, N.G. Johansson, C.L. Jordon, M.D. Kinnick, P. Lind, J.M. Morin Jr, R. Noreen, B. Oberg, J.A. Palkowitz, C.A. Parrish, P. Pranc, C. Sahlberg, R.J. Ternansky, R.T. Vasileff, L. Vrang, S.J. West, H. Zhang, X.X. Zhou, J. Med. Chem. 38, 4929 (1995)CrossRefGoogle Scholar
  16. 16.
    J.L. Buchanan, R.S. Bohacek, G.P. Luke, M. Hatada, X. Lu, D.C. Dalgarno, S.S. Narula, R. Yuan, D.A. Holt, Bioorg. Med. Chem. Lett. 9, 2353 (1999)CrossRefGoogle Scholar
  17. 17.
    D.E. Thurston, D.S. Bose, A.S. Thompson, P.W. Howard, A. Leoni, S.J. Croker, T.C. Jenkins, S. Neidle, J.A. Hartley, L.H. Hurley, J. Org. Chem. 61, 8141 (1996)CrossRefGoogle Scholar
  18. 18.
    A. Kamal, N. Laxman, G. Ramesh, K. Neelima, A.K. Kondapi, Chem. Commun. 35, 437 (2001)CrossRefGoogle Scholar
  19. 19.
    A. Raasch, O. Scharfenstein, C. Traenkle, U. Holzgrabe, K. Mohr, J. Med. Chem. 45, 3809 (2002)CrossRefGoogle Scholar
  20. 20.
    J. Christoffers, A. Mann, Angew. Chem. Int. Ed. 40, 4591 (2001)CrossRefGoogle Scholar
  21. 21.
    B. Jayashankar, K.M. Lokanath Rai, N. Baskaran, H.S. Sathish, Eur. J. Med. Chem. 44, 3898 (2009)CrossRefGoogle Scholar
  22. 22.
    S. Hachiya, D. Hashizume, Sh Maki, H. Niwa, T. Hirano, Tetrahedron Lett. 51, 1401 (2010)CrossRefGoogle Scholar
  23. 23.
    S. Beveridge, R.L. Harris, Aust. J. Chem. 24, 1229 (1971)CrossRefGoogle Scholar
  24. 24.
    T. Hino, K. Hoji, S. Acaboshi, Chem. Pharm. Bull. 18, 384 (1970)CrossRefGoogle Scholar
  25. 25.
    L. Garuti, M. Roberti, A. Pession, E. Leoncini, S. Hrelia, Bioorg. Med. Chem. Lett. 11, 3147 (2001)CrossRefGoogle Scholar
  26. 26.
    C.J. Moody, E. Swann, J. Med. Chem. 38, 1039 (1995)CrossRefGoogle Scholar
  27. 27.
    D. Uzun, H. Arslan, A.B. Gündüzalp, E. Hasdemir, Surf. Coat. Technol. 239, 108 (2014)CrossRefGoogle Scholar
  28. 28.
    T. Funakoshi, S. Chaki, N. Kawashima, Y. Suzuki, R. Yoshikawa, T. Kumagai, A. Nakazato, K. Kameo, M. Goto, Sh Okuyama, Life Sci. 71, 1371 (2002)CrossRefGoogle Scholar
  29. 29.
    N.O. Mahmoodi, S. Shoja, K. Tabatabaeian, B. Sharifzadeh, Ultrason. Sonochem. 23, 31 (2015)CrossRefGoogle Scholar
  30. 30.
    Z. Khodaee, A. Yahyazadeh, N.O. Mahmoodi, J. Heterocycl. Chem. 50, 288 (2013)CrossRefGoogle Scholar
  31. 31.
    A. Rineh, N.O. Mahmoodi, M. Abdollahi, A. Foroumadi, M. Sorkhi, A. Shafiee, Arch. Pharm. Chem. Life Sci. 340, 409 (2007)CrossRefGoogle Scholar
  32. 32.
    N.O. Mahmoodi, J. Parvizi, B. Sharifzadeh, M. Rassa, Arch. Pharm. Chem. Life Sci. 346, 860 (2013)CrossRefGoogle Scholar
  33. 33.
    B. Sharifzadeh, N.O. Mahmoodi, M. Mamaghani, Kh Tabatabaeian, A. Salimi, I. Nikokar, Bioorg. Med. Chem. Lett. 23, 548 (2013)CrossRefGoogle Scholar
  34. 34.
    N.O. Mahmoodi, I. Nikokar, M. Farhadi, A. Ghavidast, Z. Naturforsch. 69, 715 (2014)CrossRefGoogle Scholar
  35. 35.
    N.O. Mahmoodi, A. Ghavidast, Chem. Heterocycl. Compd. 49, 1451 (2014)CrossRefGoogle Scholar
  36. 36.
    N.O. Mahmoodi, M. Namroudi, F.G. Pirbasti, H. Roohi, I. Nikokar, Res. Chem. Intermed. (2015). doi: 10.1007/s11164-015-2235-7 Google Scholar
  37. 37.
    G. Rajitha, B. Janardhan, P. Mahendar, V. Ravibabu, B. Rajitha, A. Sadanandam, R. Soc. Chem. Adv. 4, 53812 (2014)Google Scholar
  38. 38.
    G. Rajitha, V. Ravibabu, G. Ramesh, B. Rajitha, R. Jobina, B. Siddhardha, S. Vijaya Laxmi, Res. Chem. Intermed. (2015). doi: 10.1007/s11164-015-1959-8 Google Scholar
  39. 39.
    G. Rajitha, B. Janardhan, G. Ramesh, B. Rajitha, V. Yashodhara, P.A. Crooks, Bioorg. Med. Chem. Lett. 25, 106 (2015)CrossRefGoogle Scholar
  40. 40.
    G. Rajitha, B. Janardhan, P. Mahendar, V. Ravibabu, H. Sairengpuii, B. Rajitha, A. Sadanandam, B. Siddhardha, Bioorg. Med. Chem. Lett. 24, 4239 (2014)CrossRefGoogle Scholar
  41. 41.
    G. Rajitha, B. Janardhan, B. Rajitha, J. Heterocycl. Chem. (2014). doi: 10.1002/jhet.2116 Google Scholar
  42. 42.
    A.A. Hassan, Y.R. Ibrahim, E.M. El-Sheref, M. Abdel-Aziz, S. Bräse, M. Nieger, Arch. Pharm. Chem. Life Sci. 346, 562 (2013)CrossRefGoogle Scholar
  43. 43.
    F. Chimenti, A. Bolasco, D. Secci, P. Chimenti, A. Granese, S. Carradori, M. Yáñez, F. Orallo, F. Ortuso, S. Alcaro, Bioorg. Med. Chem. 18, 5715 (2010)CrossRefGoogle Scholar
  44. 44.
    S.K. Bharti, G. Nath, R. Tilak, S.K. Singh, Eur. J. Med. Chem. 45, 651 (2010)CrossRefGoogle Scholar
  45. 45.
    A.A.H. Abdel-Rahman, W.A. El-Sayed, E.G. Zaki, A.A. Mohamed, A.A. Fadda, J. Heterocycl. Chem. 49, 93 (2012)CrossRefGoogle Scholar
  46. 46.
    P. Makam, R. Kankanala, A. Prakash, T. Kannan, Eur. J. Med. Chem. 69, 564 (2013)CrossRefGoogle Scholar
  47. 47.
    D.R. Richardson, D.S. Kalinowski, V. Richardson, P.C. Sharpe, D.B. Lovejoy, M. Islam, P.V. Bernhardt, J. Med. Chem. 52, 1459 (2009)CrossRefGoogle Scholar
  48. 48.
    X.H. Gu, X.Z. Wan, B. Jiang, Bioorg. Med. Chem. Lett. 9, 569 (1999)CrossRefGoogle Scholar
  49. 49.
    F.G. Pirbasti, N.O. Mahmoodi, Mol. Divers. (2015). doi: 10.1007/s11030-015-9654-7 Google Scholar

Copyright information

© Springer Science+Business Media Dordrecht 2016

Authors and Affiliations

  • Nosrat O. Mahmoodi
    • 1
    Email author
  • Behzad Khalili
    • 1
  • Olia Rezaeianzade
    • 1
  • Atefeh Ghavidast
    • 1
  1. 1.Department of Organic Chemistry, Faculty of SciencesUniversity of GuilanRashtIran

Personalised recommendations