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

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Abstract

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 5a–d and 6a–d 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 5а–d were found to exhibit a weak selective activity against Gram-positive bacteria of Bacillus subtilis and compounds 6а–d against Gram-negative bacteria of Escherichia coli.

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Acknowledgements

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).

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Authors and Affiliations

  1. Acad. S.Yu. Yunusov Institute of the Chemistry of Plant Substances, Academy of Sciences of the Republic of Uzbekistan, 77, M. Ulugbek str., Tashkent, 100170, Uzbekistan

    D. S. Ismailova, A. A. Ziyaev, Kh. M. Bobakulov, S. A. Sasmakov, U. S. Makhmudov, E. G. Yusupova & Sh. S. Azimova

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  1. D. S. Ismailova
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  2. A. A. Ziyaev
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  3. Kh. M. Bobakulov
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  4. S. A. Sasmakov
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  5. U. S. Makhmudov
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  6. E. G. Yusupova
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  7. Sh. S. Azimova
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Correspondence to A. A. Ziyaev.

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Ismailova, D.S., Ziyaev, A.A., Bobakulov, K.M. et al. The new Schiff bases of 2-alkylthio-5-(4-aminophenyl)-1,3,4-oxadiazoles and their antimicrobial activity. J IRAN CHEM SOC 16, 545–551 (2019). https://doi.org/10.1007/s13738-018-1530-9

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