Journals / Gazi University Journal of Science / 2026 / Volume: 29 Issue: 2

Synthesis of N-(Aryl)-2-(phenylselanyl)acetamides and Their Antimicrobial Activities

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Publication Date
2016-06-20
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AI Summary & Key Takeaways

AI Insight
⚡ TL;DR(Too Long; Didn't Read)

All the compounds showed moderate antioxidant activities.

📌 3 Key Takeaways

🎯
Objective & Hypothesis:Novel N -(aryl)-2-(phenylselanyl)acetamides ( 5a -5l, 6, 7 ) were synthesized by the reaction of 2-(phenylselanyl)acetyl chloride with substitute arylamine derivatives in dry benzene .
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Key Findings & Data:The structures of these compounds were characterized by the spectroscopic methods such as FT-IR, 1 H-NMR, 13 C NMR and HRMS.
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Conclusion & Impact:All the compounds showed moderate antioxidant activities.
🔬Design:Modeling & Simulation
📍Scope:Comprehensive Sample
⚙️Variables:Selenium · antibacterial activity · antifungal activity

Abstract

Novel N -(aryl)-2-(phenylselanyl)acetamides ( 5a -5l, 6, 7 ) were synthesized by the reaction of 2-(phenylselanyl)acetyl chloride with substitute arylamine derivatives in dry benzene . The structures of these compounds were characterized by the spectroscopic methods such as FT-IR, 1 H-NMR, 13 C NMR and HRMS. Furthermore, all the synthesized compounds were tested in vitro for their antimicrobial and antifungal activity. The obtained results were compared with conventional reference antibiotics Ciprofloxacin and Griseofulvin's results. Their antioxidant potentials were evaluated using in vitro antioxidant models known as DPPH (1,1-diphenyl-2-picrylhydrazyl) radical scavenging activities. Some of the tested compounds exhibited significant antibacterial, antifungal and antioxidant activities. Particularly, compound 5h showed more pronounced activity than reference antibiotics against Staphylococcus aureus . Compounds 5f and 5i showed excellent levels of antifungal activity against Penicillium roquefortii and Aspergillus niger . All the compounds showed moderate antioxidant activities.

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Cite This Article

Yıldırır, Y., Yavuz, S., Özkan, H., Gürel, Ö. (2016). Synthesis of N-(Aryl)-2-(phenylselanyl)acetamides and Their Antimicrobial Activities. Gazi University Journal of Science, Volume: 29 Issue: 2. https://ajindex.com/articles/1269499

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References (45)

  1. M. A. Arrica, T. Wirth, Eur. J. Org. Chem. 395-403 (2005).
  2. M. A. Abramov, W. Dehaen, B. D’Hooge, M. L. Petrov, S. Smeets, S. Toppet, M. Voets, Tetrahedron, 56, 3933-3940 (2000).
  3. B. D’ Hooge, S. Smeets, S. Toppet, S. Dehaeam, J. Chem. Soc. Chem. Commun. 1753-1754 (1997).
  4. G. L’Abbe, B. Haelterman, W. Dehaen, J. Chem. Soc. Perkin Trans 1, 2203-2204 (1994).
  5. M. A. Smadi, S. Ratrout, Molecules 10, 1126-1134 (2005).
  6. M. P. Rayman, Lancet 356, 233-241 (2000).
  7. M. P. Rayman, Brit. Med. J. 314, 387-388 (1997).
  8. X. Chen, G. Yang, J. Chen, Z. Wen, K. Ge, Biol. Trace. Elem. Res. 2, 91-107 (1980).
  9. H. J. Jung, Y. R. Seo, Biofactors 36, 153-158 (2010).
  10. G. N. Schrauzer, Crit. Rev. Biotechnol. 29, 10-17 (2009).
  11. M. S. Stratton, A. M. Algotar, J. Ranger-Moore, S. P. Stratton, E. H. Slate, C. H. Hsu, P. A. Thompson, L. C. Clark, F. R. Ahmann, Cancer Prev. Res. 3, 1035-1043 (2010).
  12. G. Mugesh, W. W. du Mont, H. Sies, Chem Rev 101, 2125-2179 (2001).
  13. R. J. Shamberger, Biochemistry of Selenium; Academic: New York, 1972; Chapter 7.
  14. H. Özkan, S. Yavuz, A. Dişli, Y. Yıldırır, L. Türker, Heteroatom Chem. 18, 3, 255-258 (2007).
  15. S. Çete, H. Özkan, F. Arslan, Y. Yıldırır, A. Yaşar, Asian J. Chem. 19 (1), 550-554 (2007).
  16. K. L. Liao, M. C Yin, Journal of Agricultural And Food Chemistry 48, 2266-2270 (2000).
  17. B. Halliwell, R. Aeschbach, J. Löliger, O. I. Aruoma Food Chemistry and Toxicology 33, 601-617 (1995).
  18. H. Sies, European Journal of Biochemistry 215, 213-219(1993).
  19. T. H. Tseng, E. S. Kao, C. Y. Chu, F. P. Chou, H. W. Lin Wu, C. J. Wang, Food Chemistry and Toxicology 35:1159- 1164(1997).
  20. J. R. Soares, T. C. P. Dinis, A. P. Cunha, L. M. Almeida, Free Radical Research 26, 469-478(1997).
  21. E. E. Battin, J. L. Brumaghim, Cell Biochem. Biophys. 55, 1- 23 (2009).
  22. C. W. Nogueira, J. B. T. Rocha, Arch. Toxicol. 85, 1313-1359 (2011).
  23. M. Valko, D. Leibfritz, J. Moncol, M. T. D. Cronin, M. Mazur, J. Tesler, Int. J. Biochem. Cell Biol. 39, 44-84 (2007).
  24. C. W. Nogueira, G. Zeni, J. B. Rocha, Chem. Rev. 104, 6225-6285 (2004).
  25. A. Muller, E. Cadenas, P. Graf, H. Sies, Biochem. Pharmacol. 33, 3235-3239 (1984).
  26. F. C. Meotti, E. C. Stangherlin, C. W. Nogueira, J. B. T. Rocha, Environ. Res. 94, 276-282 (2004).
  27. J. I. Rossato, L. A. Ketzer, F. B. Centuriao, S. J. N. Silva, D. S. Lüdtke, G. Zeni, A. L. Braga, M. A. Rubin, J. B. T. Rocha, Neurochem. Res. 27, 297-303 (2002).
  28. L. Savegnago, C. R. Jesse, A. V. Moro, V. C. Borges, F. W. Santos, J. B. Rocha, C. W. Pharmacol. Biochem. Behav. 83, 221-229 (2006).
  29. E. A. Wilhelm, C. R. Jesse, C. F. Bortolatto, C. W. Nogueira, Fund. Clin. Pharmacol. 25, 80-90 (2011).
  30. G. R. M. Dias, F. A. Vieira, F. Dobrachinski, J. C. Bridi, R. De, S. Balk, F. A. Soares, C. W. Nogueira, N. B. V. Barbosa, Int. J. Dev. Neurosci. 30, 83-89 (2012).
  31. C. R. Jesse, L. Savegnago, C. W. Nogueira, J. Pharm. Pharmacol. 61, 623-630 (2009).
  32. C. A. Bruning, A. C. Souza, B. M. Gai, G. Zeni, C. W. Nogueira, Eur. J. Pharmacol. 658, 145-149 (2011).
  33. B. M. Gai, A. L. Stein, J. A. Roehrs, F. N. Bilheri, C. W. Nogueira, G. Zeni, Org. Biomol. Chem. 10, 798-807(2012).
  34. L. Savegnago, C. R. Jesse, L. G. Pinto, J. B. Rocha, C. W. Nogueira, G. Zeni, Prog. Neuropsycopharmacol. Biol. Psychiatry 31, 1261-1269 (2007).
  35. N. F. Pavin, F. Donato, F. W. Cibin, C. R. Jesse, P. H. Schneider, H. D. de Salles, L. A. Soares, D. Alvez, L. Savegnago, Eur. J. Pharmacol. 668, 169-176 (2011).
  36. C. F. Bortolatto, E. A. Wilhelm, P. M. Chagas, C. W. Nogueira, Biogerontology 13, 237-249 (2011).
  37. E. A. Wilhelm, C. R. Jesse, C. F. Bortolatto, N. B. Barbosa, C. W. Nogueira, J. Pharm. Pharmacol. 62, 1121-1127 (2010).
  38. O. Micke, L. Schomburg, J. Buentzel, K. Kisters, R. Muecke, Molecules 14, 3975-3988 (2009).
  39. F. R. Brigelius, Chem. Biodivers. 5, 389-395, 2008.
  40. A. C. Pappas, E. Zoidis, P. F. Surai, G. Zervas, Comp.
  41. Biochem. Physiol. B Biochem. Mol. Biol. 151, 361-372. 2008.
  42. R. Muecke, L. Schomburg, J. Buentzel, K. Kisters, O. Micke, Integr. Cancer. Ther. 9, 136-141(2010).
  43. G. M. Soriano, Curr. Med. Chem. 11, 1657-1669 (2004).
  44. S. Yavuz, A. Dişli, Y. Yıldırır, L. Türker, Molecules 10, 1000-1004 (2005).
  45. D. V. Rajakumar, M. N. A. Rao, Free Radic. Res. 22(4), 309-317 (1995).