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Year 2016, Volume: 29 Issue: 2, 309 - 315, 20.06.2016

Abstract

References

  • M. A. Arrica, T. Wirth, Eur. J. Org. Chem. 395-403 (2005).
  • M. A. Abramov, W. Dehaen, B. D’Hooge, M. L. Petrov, S. Smeets, S. Toppet, M. Voets, Tetrahedron, 56, 3933-3940 (2000).
  • B. D’ Hooge, S. Smeets, S. Toppet, S. Dehaeam, J. Chem. Soc. Chem. Commun. 1753-1754 (1997).
  • G. L’Abbe, B. Haelterman, W. Dehaen, J. Chem. Soc. Perkin Trans 1, 2203-2204 (1994).
  • M. A. Smadi, S. Ratrout, Molecules 10, 1126-1134 (2005).
  • M. P. Rayman, Lancet 356, 233-241 (2000).
  • M. P. Rayman, Brit. Med. J. 314, 387-388 (1997).
  • X. Chen, G. Yang, J. Chen, Z. Wen, K. Ge, Biol. Trace. Elem. Res. 2, 91-107 (1980).
  • H. J. Jung, Y. R. Seo, Biofactors 36, 153-158 (2010).
  • G. N. Schrauzer, Crit. Rev. Biotechnol. 29, 10-17 (2009).
  • 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).
  • G. Mugesh, W. W. du Mont, H. Sies, Chem Rev 101, 2125-2179 (2001).
  • R. J. Shamberger, Biochemistry of Selenium; Academic: New York, 1972; Chapter 7.
  • H. Özkan, S. Yavuz, A. Dişli, Y. Yıldırır, L. Türker, Heteroatom Chem. 18, 3, 255-258 (2007).
  • S. Çete, H. Özkan, F. Arslan, Y. Yıldırır, A. Yaşar, Asian J. Chem. 19 (1), 550-554 (2007).
  • K. L. Liao, M. C Yin, Journal of Agricultural And Food Chemistry 48, 2266-2270 (2000).
  • B. Halliwell, R. Aeschbach, J. Löliger, O. I. Aruoma Food Chemistry and Toxicology 33, 601-617 (1995).
  • H. Sies, European Journal of Biochemistry 215, 213-219(1993).
  • 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).
  • J. R. Soares, T. C. P. Dinis, A. P. Cunha, L. M. Almeida, Free Radical Research 26, 469-478(1997).
  • E. E. Battin, J. L. Brumaghim, Cell Biochem. Biophys. 55, 1- 23 (2009).
  • C. W. Nogueira, J. B. T. Rocha, Arch. Toxicol. 85, 1313-1359 (2011).
  • M. Valko, D. Leibfritz, J. Moncol, M. T. D. Cronin, M. Mazur, J. Tesler, Int. J. Biochem. Cell Biol. 39, 44-84 (2007).
  • C. W. Nogueira, G. Zeni, J. B. Rocha, Chem. Rev. 104, 6225-6285 (2004).
  • A. Muller, E. Cadenas, P. Graf, H. Sies, Biochem. Pharmacol. 33, 3235-3239 (1984).
  • F. C. Meotti, E. C. Stangherlin, C. W. Nogueira, J. B. T. Rocha, Environ. Res. 94, 276-282 (2004).
  • 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).
  • 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).
  • E. A. Wilhelm, C. R. Jesse, C. F. Bortolatto, C. W. Nogueira, Fund. Clin. Pharmacol. 25, 80-90 (2011).
  • 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).
  • C. R. Jesse, L. Savegnago, C. W. Nogueira, J. Pharm. Pharmacol. 61, 623-630 (2009).
  • C. A. Bruning, A. C. Souza, B. M. Gai, G. Zeni, C. W. Nogueira, Eur. J. Pharmacol. 658, 145-149 (2011).
  • B. M. Gai, A. L. Stein, J. A. Roehrs, F. N. Bilheri, C. W. Nogueira, G. Zeni, Org. Biomol. Chem. 10, 798-807(2012).
  • L. Savegnago, C. R. Jesse, L. G. Pinto, J. B. Rocha, C. W. Nogueira, G. Zeni, Prog. Neuropsycopharmacol. Biol. Psychiatry 31, 1261-1269 (2007).
  • 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).
  • C. F. Bortolatto, E. A. Wilhelm, P. M. Chagas, C. W. Nogueira, Biogerontology 13, 237-249 (2011).
  • E. A. Wilhelm, C. R. Jesse, C. F. Bortolatto, N. B. Barbosa, C. W. Nogueira, J. Pharm. Pharmacol. 62, 1121-1127 (2010).
  • O. Micke, L. Schomburg, J. Buentzel, K. Kisters, R. Muecke, Molecules 14, 3975-3988 (2009).
  • F. R. Brigelius, Chem. Biodivers. 5, 389-395, 2008.
  • A. C. Pappas, E. Zoidis, P. F. Surai, G. Zervas, Comp.
  • Biochem. Physiol. B Biochem. Mol. Biol. 151, 361-372. 2008.
  • R. Muecke, L. Schomburg, J. Buentzel, K. Kisters, O. Micke, Integr. Cancer. Ther. 9, 136-141(2010).
  • G. M. Soriano, Curr. Med. Chem. 11, 1657-1669 (2004).
  • S. Yavuz, A. Dişli, Y. Yıldırır, L. Türker, Molecules 10, 1000-1004 (2005).
  • D. V. Rajakumar, M. N. A. Rao, Free Radic. Res. 22(4), 309-317 (1995).

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

Year 2016, Volume: 29 Issue: 2, 309 - 315, 20.06.2016

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, 1H-NMR, 13C 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.

References

  • M. A. Arrica, T. Wirth, Eur. J. Org. Chem. 395-403 (2005).
  • M. A. Abramov, W. Dehaen, B. D’Hooge, M. L. Petrov, S. Smeets, S. Toppet, M. Voets, Tetrahedron, 56, 3933-3940 (2000).
  • B. D’ Hooge, S. Smeets, S. Toppet, S. Dehaeam, J. Chem. Soc. Chem. Commun. 1753-1754 (1997).
  • G. L’Abbe, B. Haelterman, W. Dehaen, J. Chem. Soc. Perkin Trans 1, 2203-2204 (1994).
  • M. A. Smadi, S. Ratrout, Molecules 10, 1126-1134 (2005).
  • M. P. Rayman, Lancet 356, 233-241 (2000).
  • M. P. Rayman, Brit. Med. J. 314, 387-388 (1997).
  • X. Chen, G. Yang, J. Chen, Z. Wen, K. Ge, Biol. Trace. Elem. Res. 2, 91-107 (1980).
  • H. J. Jung, Y. R. Seo, Biofactors 36, 153-158 (2010).
  • G. N. Schrauzer, Crit. Rev. Biotechnol. 29, 10-17 (2009).
  • 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).
  • G. Mugesh, W. W. du Mont, H. Sies, Chem Rev 101, 2125-2179 (2001).
  • R. J. Shamberger, Biochemistry of Selenium; Academic: New York, 1972; Chapter 7.
  • H. Özkan, S. Yavuz, A. Dişli, Y. Yıldırır, L. Türker, Heteroatom Chem. 18, 3, 255-258 (2007).
  • S. Çete, H. Özkan, F. Arslan, Y. Yıldırır, A. Yaşar, Asian J. Chem. 19 (1), 550-554 (2007).
  • K. L. Liao, M. C Yin, Journal of Agricultural And Food Chemistry 48, 2266-2270 (2000).
  • B. Halliwell, R. Aeschbach, J. Löliger, O. I. Aruoma Food Chemistry and Toxicology 33, 601-617 (1995).
  • H. Sies, European Journal of Biochemistry 215, 213-219(1993).
  • 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).
  • J. R. Soares, T. C. P. Dinis, A. P. Cunha, L. M. Almeida, Free Radical Research 26, 469-478(1997).
  • E. E. Battin, J. L. Brumaghim, Cell Biochem. Biophys. 55, 1- 23 (2009).
  • C. W. Nogueira, J. B. T. Rocha, Arch. Toxicol. 85, 1313-1359 (2011).
  • M. Valko, D. Leibfritz, J. Moncol, M. T. D. Cronin, M. Mazur, J. Tesler, Int. J. Biochem. Cell Biol. 39, 44-84 (2007).
  • C. W. Nogueira, G. Zeni, J. B. Rocha, Chem. Rev. 104, 6225-6285 (2004).
  • A. Muller, E. Cadenas, P. Graf, H. Sies, Biochem. Pharmacol. 33, 3235-3239 (1984).
  • F. C. Meotti, E. C. Stangherlin, C. W. Nogueira, J. B. T. Rocha, Environ. Res. 94, 276-282 (2004).
  • 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).
  • 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).
  • E. A. Wilhelm, C. R. Jesse, C. F. Bortolatto, C. W. Nogueira, Fund. Clin. Pharmacol. 25, 80-90 (2011).
  • 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).
  • C. R. Jesse, L. Savegnago, C. W. Nogueira, J. Pharm. Pharmacol. 61, 623-630 (2009).
  • C. A. Bruning, A. C. Souza, B. M. Gai, G. Zeni, C. W. Nogueira, Eur. J. Pharmacol. 658, 145-149 (2011).
  • B. M. Gai, A. L. Stein, J. A. Roehrs, F. N. Bilheri, C. W. Nogueira, G. Zeni, Org. Biomol. Chem. 10, 798-807(2012).
  • L. Savegnago, C. R. Jesse, L. G. Pinto, J. B. Rocha, C. W. Nogueira, G. Zeni, Prog. Neuropsycopharmacol. Biol. Psychiatry 31, 1261-1269 (2007).
  • 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).
  • C. F. Bortolatto, E. A. Wilhelm, P. M. Chagas, C. W. Nogueira, Biogerontology 13, 237-249 (2011).
  • E. A. Wilhelm, C. R. Jesse, C. F. Bortolatto, N. B. Barbosa, C. W. Nogueira, J. Pharm. Pharmacol. 62, 1121-1127 (2010).
  • O. Micke, L. Schomburg, J. Buentzel, K. Kisters, R. Muecke, Molecules 14, 3975-3988 (2009).
  • F. R. Brigelius, Chem. Biodivers. 5, 389-395, 2008.
  • A. C. Pappas, E. Zoidis, P. F. Surai, G. Zervas, Comp.
  • Biochem. Physiol. B Biochem. Mol. Biol. 151, 361-372. 2008.
  • R. Muecke, L. Schomburg, J. Buentzel, K. Kisters, O. Micke, Integr. Cancer. Ther. 9, 136-141(2010).
  • G. M. Soriano, Curr. Med. Chem. 11, 1657-1669 (2004).
  • S. Yavuz, A. Dişli, Y. Yıldırır, L. Türker, Molecules 10, 1000-1004 (2005).
  • D. V. Rajakumar, M. N. A. Rao, Free Radic. Res. 22(4), 309-317 (1995).
There are 45 citations in total.

Details

Primary Language English
Subjects Engineering
Journal Section Chemistry
Authors

Yılmaz Yıldırır

Serkan Yavuz This is me

Hamdi Özkan This is me

Özge Gürel This is me

Publication Date June 20, 2016
Published in Issue Year 2016 Volume: 29 Issue: 2

Cite

APA 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, 29(2), 309-315.
AMA Yıldırır Y, Yavuz S, Özkan H, Gürel Ö. Synthesis of N-(Aryl)-2-(phenylselanyl)acetamides and Their Antimicrobial Activities. Gazi University Journal of Science. June 2016;29(2):309-315.
Chicago Yıldırır, Yılmaz, Serkan Yavuz, Hamdi Özkan, and Özge Gürel. “Synthesis of N-(Aryl)-2-(phenylselanyl)acetamides and Their Antimicrobial Activities”. Gazi University Journal of Science 29, no. 2 (June 2016): 309-15.
EndNote Yıldırır Y, Yavuz S, Özkan H, Gürel Ö (June 1, 2016) Synthesis of N-(Aryl)-2-(phenylselanyl)acetamides and Their Antimicrobial Activities. Gazi University Journal of Science 29 2 309–315.
IEEE Y. Yıldırır, S. Yavuz, H. Özkan, and Ö. Gürel, “Synthesis of N-(Aryl)-2-(phenylselanyl)acetamides and Their Antimicrobial Activities”, Gazi University Journal of Science, vol. 29, no. 2, pp. 309–315, 2016.
ISNAD Yıldırır, Yılmaz et al. “Synthesis of N-(Aryl)-2-(phenylselanyl)acetamides and Their Antimicrobial Activities”. Gazi University Journal of Science 29/2 (June 2016), 309-315.
JAMA Yıldırır Y, Yavuz S, Özkan H, Gürel Ö. Synthesis of N-(Aryl)-2-(phenylselanyl)acetamides and Their Antimicrobial Activities. Gazi University Journal of Science. 2016;29:309–315.
MLA Yıldırır, Yılmaz et al. “Synthesis of N-(Aryl)-2-(phenylselanyl)acetamides and Their Antimicrobial Activities”. Gazi University Journal of Science, vol. 29, no. 2, 2016, pp. 309-15.
Vancouver Yıldırır Y, Yavuz S, Özkan H, Gürel Ö. Synthesis of N-(Aryl)-2-(phenylselanyl)acetamides and Their Antimicrobial Activities. Gazi University Journal of Science. 2016;29(2):309-15.