Chemistry of Heterocyclic Compounds

, Volume 48, Issue 2, pp 362–367 | Cite as

Synthesis of 5-(4-aminophenyl)-2-(arylamino)-1,3,4-thiadiazoles and their schiff base derivatives as antimycobacterial agents

  • K. A. DilmaghaniEmail author
  • N. H. Jazani
  • F. Nasuhi Pur
  • N. Shokoufeh
  • F. Ghadiri
  • F. M. Fakhraee

The condensation reaction of 5-(4-aminophenyl)-N-aryl-1,3,4-thiadiazol-2-ylamines with salicyl-aldehyde, 3-hydroxybenzaldehyde, 4-hydroxybenzaldehyde, 5-bromosalicylaldehyde, 5-chlorosalicyl-aldehyde, 4-methoxybenzaldehyde, 3-nitrobenzaldehyde, and 4-nitrobenzaldehyde results in series of new Schiff bases. The synthesized compounds were tested for their antimicrobial efficiency against Mycobacterium smegmatis PTCC 1307 in vitro. All compounds showed significant antiproliferative activity against M. smegmatis.


salicylaldehyde 1,3,4-thiadiazole in vitro Mycobacterium smegmatis Schiff base 


  1. 1.
    E. L. Corbett, C. J. Watt, N. Walker, D. Maher, B. G. Williams, M. C. Raviglione, and C. Dye, Arch. Intern. Med., 163, 1009 (2003).CrossRefGoogle Scholar
  2. 2.
    V. Chaturvedi, N. Dwivedi, R. P. Tripathi, and S. Sinha, J. Gen. Appl. Microbiol., 53, 333 (2007).CrossRefGoogle Scholar
  3. 3.
    F. Clerici, D. Pocar, M. Guido, A. Loche, V. Perlini, and M. Brufani, J. Med. Chem., 44, 931 (2001).CrossRefGoogle Scholar
  4. 4.
    V. Jatav, P. Mishra, S. Kashaw, and J. P. Stables, Eur. J. Med. Chem., 43, 1945 (2008).CrossRefGoogle Scholar
  5. 5.
    A. Gagnon, S. Landry, R. Coulombe, A. Jakalian, I. Guse, B. Thavonekham, P. R. Bonneau, C. Yoakim, and B. Simoneau, Bioorg. Med. Chem. Lett., 19, 1199 (2009).CrossRefGoogle Scholar
  6. 6.
    T. Wang, Y.-H. Zhang, S. Yu, H. Ji, Y.-S. Lai, and S.-X. Peng, Chin. Chem. Lett., 19, 928 (2008).CrossRefGoogle Scholar
  7. 7.
    W. Rzeski, J. Matysiak, and M. Kandefer-Szerszen, Bioorg. Med. Chem., 15, 3201 (2007).CrossRefGoogle Scholar
  8. 8.
    A. Senff-Ribeiro, A. Echevarria, E. F. Silva, S. S. Veiga, and M. B. Oliveira, Anticancer Drugs, 15, 269 (2004).CrossRefGoogle Scholar
  9. 9.
    V. Padmavathi, G. S. Reddy, A. Padmaja, P. Kondaiah, and Ali-Shazia, Eur. J. Med. Chem., 44, 2106 (2009).CrossRefGoogle Scholar
  10. 10.
    J. Matysiak, A. Nasulewicz, M. Pelczynska, M. Switalska, I. Jaroszewicz, and A. Opolski, Eur. J. Med. Chem., 41, 475 (2006).CrossRefGoogle Scholar
  11. 11.
    S. N. Swamy, B. S. Basappa, P. B. Prabhuswamy, B. H. Doreswamy, J. S. Prasad, and K. S. Rangappa, Eur. J. Med. Chem., 41, 531 (2006).CrossRefGoogle Scholar
  12. 12.
    A. Foroumadi, S. Mansouri, Z. Kiani, and A. Rahmani, Eur. J. Med. Chem., 38, 851 (2003).CrossRefGoogle Scholar
  13. 13.
    R. H. Udupi, A. Kushnoor, and A. R. Bhat, J. Indian Chem. Soc., 76, 461 (1999).Google Scholar
  14. 14.
    S. Schenone, C. Brullo, O. Bruno, F. Bondavalli, A. Ranise, W. Filippelli, B. Rinaldi, A. Capuano, and G. Falcone, Bioorg. Med. Chem., 14, 1698 (2006).CrossRefGoogle Scholar
  15. 15.
    A. A. Kadi, N. R. El-Brollosy, O. A. Al-Deeb, E. E. Habib, T. M. Ibrahim, and A. A. El-Emam, Eur. J. Med. Chem., 42, 235 (2007).CrossRefGoogle Scholar
  16. 16.
    H. M. Hirpara, V. A. Sodha, A. M. Trivedi, B. L. Khatri, and A. R. Parikh, Indian J. Chem., 42B, 1756 (2003).Google Scholar
  17. 17.
    S. Turner, M. Myers, B. Gadie, A. J. Nelson, R. Pape, J. F. Saville, J. C. Doxey, and T. L. Berridge, J. Med. Chem., 31, 902 (1988).CrossRefGoogle Scholar
  18. 18.
    M. Yusuf, R. A. Khan, and B. Ahmed, Bioorg. Med. Chem., 16, 8029 (2008).CrossRefGoogle Scholar
  19. 19.
    F. Poorrajab, S. K. Ardestani, S. Emami, M. Behrouzi-Fardmoghadam, A. Shafiee, and A. Foroumadi, Eur. J. Med. Chem., 44, 1758 (2009).CrossRefGoogle Scholar
  20. 20.
    A. Foroumadi, M. Mirzaei, and A. Shafiee, Pharmazie, 56, 610 (2001).Google Scholar
  21. 21.
    M. G. Mamolo, V. Falagiani, D. Zanpieir, and L. Vio, E. Banfi, Farmaco, 56, 587 (2001).CrossRefGoogle Scholar
  22. 22.
    M. G. Mamolo, V. Falagiani, D. Zanpieir, L. Vio, E. Banfi, and G. Scialino, Farmaco, 58, 631 (2003).CrossRefGoogle Scholar
  23. 23.
    S. Karakus, S. Rollas, Farmaco, 57, 577 (2002).CrossRefGoogle Scholar
  24. 24.
    A. Foroumadi, Z. Kargar, A. Sakhteman, Z. Sharifzadeh, R. Feyzmohammadi, M. Kazemi, and A. Shafiee, Bioorg. Med. Chem. Lett., 16, 1164 (2006).CrossRefGoogle Scholar
  25. 25.
    K. A. Dilmaghani, N. H. Jazani, A. Behrouz, and F. M. Fakhraee, Asian J. Chem., 21, 5947 (2009).Google Scholar
  26. 26.
    A. H. Abd El Rahman, and E. M. Ismail, Arzneim. Forsch., 26, 756 (1976).Google Scholar
  27. 27.
    H. N. Dogan, S. Buyuktimkin, S. Rollas, E. Yemni, and A. Cevikbas, Farmaco, 52, 565 (1997).Google Scholar
  28. 28.
    S. M. Sh. Atta and A. Ammen, Arzneim. Forsch.., 43, 1354 (1993).Google Scholar
  29. 29.
    M. G. Dhapalapur, S. S. Sabnis, and C. V. Deliwala, J. Med. Chem., 11, 1014 (1968).CrossRefGoogle Scholar
  30. 30.
    J. Patole, D. Shingnapurkar, S. Padhye, and C. Ratledge, Bioorg. Med. Chem. Lett., 16, 1514 (2006).CrossRefGoogle Scholar
  31. 31.
    N. Kalyoncuoglu, S. Rollas, D. Sur-Altıner, Y. Yegenoglu, and O. Ang, Pharmazie, 47, 796 (1992).Google Scholar
  32. 32.
    S. Karakus, Ph. D. thesis, Marmara University, Institution of Healt Sciences (2001).Google Scholar
  33. 33.
    A. Szady-Chelmieniecka, E. Grech, Z. Rozwadowski, T. Dziembowska, W. Schilf, and B. Kamienski, J. Mol. Struct., 565566, 125 (2001).CrossRefGoogle Scholar
  34. 34.
    S. Rollas, J. Pharm. Univ. Marmara, 1, 59 (1985).Google Scholar
  35. 35.
    E. J. Baron and S. M. Finegold, Bailey and Scott's Diagnostic Microbiology, 8th ed., Mosby, New York (1990).Google Scholar

Copyright information

© Springer Science+Business Media, Inc. 2012

Authors and Affiliations

  • K. A. Dilmaghani
    • 1
    Email author
  • N. H. Jazani
    • 2
  • F. Nasuhi Pur
    • 1
  • N. Shokoufeh
    • 1
  • F. Ghadiri
    • 1
  • F. M. Fakhraee
    • 3
  1. 1.Urmia UniversityUrmiaIran
  2. 2.Urmia Medical Science UniversityUrmiaIran
  3. 3.Institute of Standard and Industrial Research of IranUrmiaIran

Personalised recommendations