Journal of the Iranian Chemical Society

, Volume 16, Issue 3, pp 545–551 | Cite as

The new Schiff bases of 2-alkylthio-5-(4-aminophenyl)-1,3,4-oxadiazoles and their antimicrobial activity

  • D. S. Ismailova
  • A. A. ZiyaevEmail author
  • Kh. M. Bobakulov
  • S. A. Sasmakov
  • U. S. Makhmudov
  • E. G. Yusupova
  • Sh. S. Azimova
Original Paper


By the reaction of 5-(4-aminophenyl)-1,3,4-oxadiazolin-2-thione with alkyl halides 2-alkylthio-5-(4-aminophenyl)-1,3,4-oxadiazoles, 2–4 were obtained. By the reaction of compounds 2–4 with aromatic aldehydes, new Schiff bases 5ad and 6ad were synthesized. The structures of synthesized compounds are confirmed by the IR, UV, 1H NMR for all compounds, 13C NMR for compounds 3, 4, 5a–5d, 6a, 6d and X-ray for compound 3. All substances were tested in vitro for their antibacterial and antifungal activity. The results showed that Compound 2 exhibited remarkable activity against Candida albicans. Compounds d were found to exhibit a weak selective activity against Gram-positive bacteria of Bacillus subtilis and compounds d against Gram-negative bacteria of Escherichia coli.


5-(4-Aminophenyl)-1,3,4-oxadiazol-2-thione Aromatic aldehyde Amino group NMR spectra X-ray analysis Antimicrobial activity 



Authors are thankful to the Academy of Sciences of the Republic of Uzbekistan for supporting this study (Grant VA-FA-F7-006 and FA-F6-T198).

Compliance with ethical standards

Conflict of interest

There is no conflict of interest associated with the authors of this paper.


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Copyright information

© Iranian Chemical Society 2018

Authors and Affiliations

  • D. S. Ismailova
    • 1
  • A. A. Ziyaev
    • 1
    Email author
  • Kh. M. Bobakulov
    • 1
  • S. A. Sasmakov
    • 1
  • U. S. Makhmudov
    • 1
  • E. G. Yusupova
    • 1
  • Sh. S. Azimova
    • 1
  1. 1.Acad. S.Yu. Yunusov Institute of the Chemistry of Plant Substances, Academy of Sciences of the Republic of UzbekistanTashkentUzbekistan

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