Copyright (c) 2020 AJC
This work is licensed under a Creative Commons Attribution 4.0 International License.
Synthesis, Characterization and Antimicrobial Activity of N-2-(4-Chlorophenyl)acetyl Derivatives of (S)-Amino Acids
Corresponding Author(s) : P. Raghavendra Kumar
Asian Journal of Chemistry,
Vol. 32 No. 2 (2020): Vol 32 Issue 2
Abstract
This paper reports the synthesis, characterization and antibacterial activity of N-2-(4-chlorophenyl)acetyl derivatives of various (S)-amino acids such as (S)-alanine, (S)-phenylalanine, (S)-leucine, (S)-methionine, (S)-proline and (S)-tryptophane. These compounds have been successfully synthesized and their structures were confirmed by 1H NMR and 13C NMR and FT-IR spectroscopy. The antimicrobial activity of these six (S)-amino acids derivatives have been evaluated by the agar well diffusion method against pathogens both Gram-positive (S. aureus) and Gram-negative (K. aerogenes, E. coli and P. desmolyticumas) bacteria and fungi (A. flavus and C. albicans). All these compounds have shown mild to moderate antimicrobial activity.
Keywords
Download Citation
Endnote/Zotero/Mendeley (RIS)BibTeX
- A. Sánchez and A. Vázquez, Food Qual. Saf., 1, 29 (2017); https://doi.org/10.1093/fqs/fyx006.
- D.V. Grishin, D.D. Zhdanov, M.V. Pokrovskaya and N.N. Sokolov, All Life, 13, 11 (2020); https://doi.org/10.1080/21553769.2019.1622596.
- A.K. Pathak, V. Pathak, L.E. Seitz, W.J. Suling and R.C. Reynolds, Bioorg. Med. Chem., 21, 1685 (2013); https://doi.org/10.1016/j.bmc.2013.01.054.
- Y. Voynikov, G. Stavrakov, J. Tencheva and P. Peikov, Compt. Rend. Acad. Bulg. Sci., 66, 1399 (2013).
- Y. Voynikov, V. Valcheva, G. Momekov, P. Peikov and G. Stavrakov, Bioorg. Med. Chem. Lett., 24, 3043 (2014); https://doi.org/10.1016/j.bmcl.2014.05.026.
- M.M. EI-Kerdawy, M. Eisa, A. Barghash and A. Marouf, Sulfur Lett., 10, 57 (1989).
- M.E.A. El-Fattah, Arch. Pharm. Res., 21, 723 (1998); https://doi.org/10.1007/BF02976765.
- O.A. Fathalla and M.E.A. Zaki, Indian J. Chem., 37B, 484 (1998).
- E. Schnabel, H. Herzog, P. Hoffmann, E. Klauke and I. Ugi, Angew. Chem., 7, 380 (1968); https://doi.org/10.1002/anie.196803801.
- M.J. McKennon, A.I. Meyers, K. Drauz and M. Schwarm, J. Org. Chem., 58, 3568 (1993); https://doi.org/10.1021/jo00065a020.
- J. Humljan, M. Kotnik, A. Boniface, T. Solmajer, U. Urleb, D. Blanot and S. Gobec, Tetrahedron, 62, 10980 (2006); https://doi.org/10.1016/j.tet.2006.08.030.
- H.M. Hassan, M.M. Abdelall, A.M. El-Naggar, M.E. Tamer and R.A. Bayoumi, J. Am. Sci., 7, 378 (2011).
- M. Al-Amin and M.I. Rabiul, Bangladesh J. Pharmacol., 1, 21 (2006).
- R.A. El-Sayed, Phosphorus Sulfur Silicon Rel. Elem., 131, 207 (1997); https://doi.org/10.1080/10426509708031609.
- C. Cabrele, T.A. Martinek, O. Reiser and L. Berlicki, J. Med. Chem., 57, 9718 (2014); https://doi.org/10.1021/jm5010896.
- K. Phukan, M. Ganguly and N. Devi, Synth. Commun., 39, 2694 (2009); https://doi.org/10.1080/00397910802663428.
- A. Siebert, M. Wysocka, B. Krawczyk, G. Cholewiñski and J. Rachoñ, Eur. J. Med. Chem., 143, 646 (2018); https://doi.org/10.1016/j.ejmech.2017.11.094.
- C.E. Satheesh, P. Raghavendra Kumar, P. Sharma, K. Lingaraju, B.S. Palakshamurthy and H. Raja Naika, Inorg. Chim. Acta, 442, 1 (2016); https://doi.org/10.1016/j.ica.2015.11.017.
- C.E. Satheesh, P. Raghavendra Kumar, N. Shivakumar, K. Lingaraju, P. Murali Krishna, H. Raja Naika and A. Hosamani, Inorg. Chim. Acta, 495, 118929 (2019); https://doi.org/10.1016/j.ica.2019.05.028.
- A. Sen and A. Batra, Int. J. Curr. Pharm. Res., 4, 67 (2012).
References
A. Sánchez and A. Vázquez, Food Qual. Saf., 1, 29 (2017); https://doi.org/10.1093/fqs/fyx006.
D.V. Grishin, D.D. Zhdanov, M.V. Pokrovskaya and N.N. Sokolov, All Life, 13, 11 (2020); https://doi.org/10.1080/21553769.2019.1622596.
A.K. Pathak, V. Pathak, L.E. Seitz, W.J. Suling and R.C. Reynolds, Bioorg. Med. Chem., 21, 1685 (2013); https://doi.org/10.1016/j.bmc.2013.01.054.
Y. Voynikov, G. Stavrakov, J. Tencheva and P. Peikov, Compt. Rend. Acad. Bulg. Sci., 66, 1399 (2013).
Y. Voynikov, V. Valcheva, G. Momekov, P. Peikov and G. Stavrakov, Bioorg. Med. Chem. Lett., 24, 3043 (2014); https://doi.org/10.1016/j.bmcl.2014.05.026.
M.M. EI-Kerdawy, M. Eisa, A. Barghash and A. Marouf, Sulfur Lett., 10, 57 (1989).
M.E.A. El-Fattah, Arch. Pharm. Res., 21, 723 (1998); https://doi.org/10.1007/BF02976765.
O.A. Fathalla and M.E.A. Zaki, Indian J. Chem., 37B, 484 (1998).
E. Schnabel, H. Herzog, P. Hoffmann, E. Klauke and I. Ugi, Angew. Chem., 7, 380 (1968); https://doi.org/10.1002/anie.196803801.
M.J. McKennon, A.I. Meyers, K. Drauz and M. Schwarm, J. Org. Chem., 58, 3568 (1993); https://doi.org/10.1021/jo00065a020.
J. Humljan, M. Kotnik, A. Boniface, T. Solmajer, U. Urleb, D. Blanot and S. Gobec, Tetrahedron, 62, 10980 (2006); https://doi.org/10.1016/j.tet.2006.08.030.
H.M. Hassan, M.M. Abdelall, A.M. El-Naggar, M.E. Tamer and R.A. Bayoumi, J. Am. Sci., 7, 378 (2011).
M. Al-Amin and M.I. Rabiul, Bangladesh J. Pharmacol., 1, 21 (2006).
R.A. El-Sayed, Phosphorus Sulfur Silicon Rel. Elem., 131, 207 (1997); https://doi.org/10.1080/10426509708031609.
C. Cabrele, T.A. Martinek, O. Reiser and L. Berlicki, J. Med. Chem., 57, 9718 (2014); https://doi.org/10.1021/jm5010896.
K. Phukan, M. Ganguly and N. Devi, Synth. Commun., 39, 2694 (2009); https://doi.org/10.1080/00397910802663428.
A. Siebert, M. Wysocka, B. Krawczyk, G. Cholewiñski and J. Rachoñ, Eur. J. Med. Chem., 143, 646 (2018); https://doi.org/10.1016/j.ejmech.2017.11.094.
C.E. Satheesh, P. Raghavendra Kumar, P. Sharma, K. Lingaraju, B.S. Palakshamurthy and H. Raja Naika, Inorg. Chim. Acta, 442, 1 (2016); https://doi.org/10.1016/j.ica.2015.11.017.
C.E. Satheesh, P. Raghavendra Kumar, N. Shivakumar, K. Lingaraju, P. Murali Krishna, H. Raja Naika and A. Hosamani, Inorg. Chim. Acta, 495, 118929 (2019); https://doi.org/10.1016/j.ica.2019.05.028.
A. Sen and A. Batra, Int. J. Curr. Pharm. Res., 4, 67 (2012).