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The synthesis and investigation of the antimicrobial activity of some new phenylselanyl-1-(toluene-4-sulfonyl)-1H-tetrazole derivatives

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Abstract

The sulfonamide functional group has aroused interest in both medicinal and bioorganic chemistry. In this study, some new phenylselanyl–1–(toluene-4-sulfonyl)-1H-tetrazole derivatives (2a–f) have been synthesized using dicyclohexylcarbodiimide/dimethylaminopyridine (DCC/DMAP). The structures of the presently synthesized compounds were elucidated by spectroscopic methods [Fourier-transform infrared (FTIR) spectroscopy, 1H nuclear magnetic resonance (NMR), 13C nuclear magnetic resonance-attached proton test (13C NMR-APT), and mass spectrometry (MS)]. In addition, the antimicrobial activity of the synthesized compounds and two antibiotics [sulfamethoxazole (SMX) and sulfamerazine (SRZ)] were investigated against some microorganisms.

Graphical Abstract

The synthesis and investigation of the antimicrobial activity of some new phenylselanyl-1-(toluene-4-sulfonyl)-1H-tetrazole derivatives

Yılmaz Yıldırır, M. Faruk Us, Naki Çolak, Hamdi Özkan, Serkan Yavuz, Ali Disli, Sahlan Ozturk, Lemi Turker

In this study, some new phenylselanyl–1–(toluene-4-sulfonyl)-1H- tetrazole derivatives, 2a–f, have been synthesized using DCC/DMAP. In addition to, antimicrobial activity of synthesized compounds and two antibiotics (SMX, SRZ) were investigated against some microorganisms. Reagents and conditions: (i) HCI, (ii) EtONO, -5 – 0°C; (iii) KSeCN, (iv) NaN3, Et3NH+ CI−, Toluene. 2a. R1:H, R2:Cl 2b. 2a. R1:H, R2:CH3 2c. R1:Cl, R2:H 2d. R1:Br, R2:H 2e. R1:I, R2:H 2f. R1:CH3, R2:H

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Acknowledgements

We are grateful to the DPT project (no. 2001K120590) for spectral analyses.

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Authors and Affiliations

  1. Faculty of Science and Arts, Chemistry Department, Gazi University, Teknikokullar, 06500, Ankara, Turkey

    Yılmaz Yıldırır, Naki Çolak, Hamdi Özkan, Serkan Yavuz & Ali Disli

  2. Central Veterinary Controls and Research Institute, Etlik, 06250, Ankara, Turkey

    M. Faruk Us

  3. Faculty of Science and Arts, Biology Department, Gazi University, Teknikokullar, 06500, Ankara, Turkey

    Sahlan Ozturk

  4. Faculty of Science and Arts, Chemistry Department, Middle East Technical University, 06531, Ankara, Turkey

    Lemi Turker

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  1. Yılmaz Yıldırır
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  2. M. Faruk Us
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  3. Naki Çolak
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  4. Hamdi Özkan
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  5. Serkan Yavuz
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Correspondence to Yılmaz Yıldırır.

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Yıldırır, Y., Us, M.F., Çolak, N. et al. The synthesis and investigation of the antimicrobial activity of some new phenylselanyl-1-(toluene-4-sulfonyl)-1H-tetrazole derivatives. Med Chem Res 18, 91–97 (2009). https://doi.org/10.1007/s00044-008-9110-7

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  • DOI: https://doi.org/10.1007/s00044-008-9110-7

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