Synthesis, Characterization, Hydrolytic Cleavage, and Biological Activity Studies of 2-[(1e)-N-{2-[(2-{(Z)-[1-(2-Hydroxyphenyl)Ethylidene] Amino}Ethyl)Amino]Ethyl}Ethanimidoyl]Phenol
BIOACTIVITIES OF PHENOLIC SCHIFF BASES
Abstract
A Schiff base ligand 2-[(1E)-N-{2-[(2-{(Z)-[1-(2-hydroxyphenyl) ethylidene] amino}ethyl)amino]ethyl} ethanimidoyl]phenol L was hydrolyzed by copper cation which lead to formation of 8,8-dichloro-2H,3H,5H,6H-1,3-diaza-2-cupracyclopenta[1,3-a]1,3-diaza-2-cupracyclopentane hydrate (Complex), characterized by UV, IR, Powder XRD and by elemental analysis. In vitro antioxidant and anticoagulant, activities of L were evaluated. Antioxidant potential of L was assessed by DPPH scavenging, β-carotene bleaching test, hydroxyl radical scavenging method, ABTS radical scavenging test, and by reducing power test. In vitro anticoagulant effect of L at the 84 µg/mL; showed the maximum prolongation of plasma recalcification time which is comparable with that of the anticoagulant drug; heparin. In conclusion, results of the present investigation indicate that the ligand L can be a potential anticoagulant agent.
Keywords: Schiff base; Antioxidant; Free radicals; Anticoagulant.
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References
1. Z. Cimerman, S. Miljanić, N. Galić, Croat. Chem. Acta.73 (2000) 81
2. A. Gölcü, M. Tümer, H. Demirelli, RA.Wheatley, Inorg Chim Acta. 358, (2005) 1785
3. E.Yousif, E. Rentschler, N. Salih, J. Salimon, A. Hameed, M. Katan, J. Saudi Chem. Soc. 18 (2014) 269
4. S.A. Matar, W.H. Talib, M. S. Mustafa, M.S., Mubarak, M.A. AlDamen, Arab. J. Chem. 8 (2015) 850
5. A. Ourari, Y. Ouennoughi, D. Aggoun, M.S. Mubarak, E.M. Pasciak, D.G. Peters, Polyhedron. 67 (2014) 59
6. A.N. Srivastava, N.P. Singh, C.K. Shriwastaw, J. Serb. Chem. Soc.79 (2014) 421
7. Z. Aydin, M. Keles . Turk J Chem. 41 (2017) 89
8. E. Keskioglu, A. B.Gunduzalp, S. Cete, F. Hamurcu, B. Erk, Spectrochim. ActA.70 (2008) 634
9. I.J. Patel, S.J. Parmar, E-J. Chem. 7 (2010) 617
10. M. Hranjec, K. Starčević, S.K. Pavelić, P. Lučin, K. Pavelić, G. KarminskiZamola, Eur. J. Med. Chem. 46 (2011) 2274
11. P. Ronad, S. Dharbamalla, R. Hunshal, V. Maddi, Arch. Pharm. 341 (2008) 696
12. K.M. Khan, M. Taha, F. Naz, S. Siddiqui, S. Ali, F. Rahim, S. Perveen, I. Choudhary, Med. Chem. 8 (2012) 705
13. J.W. Schmidley, Stroke, 21 (1990) 1086
14. M.G. Hertog, E.J. Feskens, P.C. Hollman, M.B. Katan, D. Kromhout, Lancet. 342 (1993) 1007
15. N., Charef, F. Sebti, L. Arrar, M. Djarmouni, N. Boussoualim, A. Baghiani, S.Khennouf, A. Ourari, M.A. AlDamen, M.S. Mubarak, De.G. Peters, Polyhedron, 85 (2015) 450
16. N. Charef, L. Arrar, A. Ourari, R.M. Zalloum, M.S.Mubarak, Macromol. Sci. Pure and Appl. Chem. 47 (2010) 177
17. X.J. Duan, W.W. Zhang, X.M. Li, B.G. Wang, Food Chem. 95 (2006) 37
18. S. Boumerfeg, A. Baghiani, D. Messaoudi, S. Khennouf, L. Arrar, Phytother Res . 23 (2009) 283
19. B. Ates, L. Abraham, N. Ercal, Free Rad. Res. 42 (2008) 372
20. R. Re, N. Pellegrini, A. Proteggente, A. Pannala, M. Yang, C. Rice-Evans, Free Rad. Biol. Med. 26 (1999) 1231
21. M. Oyaizu, Jap. J. Nutr. 44 (1986)307
22. I. Gülçin, M. Oktay, E. Kirecci, O.I. Kufrevioglu,. Food Chem. 83 (2003) 371
23. P. Dey, T. Bhakta, J. Nat. Prod. Plant Resour. 2 (2012) 685
24. A.A. Emara, A.M. Ali, E.M. Ragab, A. A. El-Asmy, J. Coord. Chem. 61 (2008) 2968
25. Md. N .Alam, J. Bristi Nusrat, Md. Rafiquzzaman., Saudi Pharm. J. 21 (2013) 143
26. P. Arulpriya, P. Lalitha, S. Hemalatha, Der Chem. Sin. 1 (2010) 73
27. M. Leopoldini, N. Russo, M. Toscano, Food Chem. 125 (2011) 288
28. Zai-Qun Liu. QSAR. Comb. Sci.26 (2007) 488
29. J. Yang, J. Guo, J. Yuan, LWT – Food Sci. Tech. 41 (2008) 1060
30. S. Bicha, A. Amrani, O. Benaissa. F. León, D. Zama, I. Brouard, S. Benayache, A. Bentamene, F. Benayache, Der Pharm. Lett. 5 (2013) 24
31. S. Meir, J. Kanner, B. Akiri, S.P. Hadas, J. Agric. Food Chem. 43 (1995), 1813
32. J. Hirsh, M. O'Donnell, J.I. Weitz, Blood 105 (2005) 453
33. l. Sawant Ramesh,Mhaske, S. Mahesh, B. WadekarJyoti, Int. J. Pharm. Pharm. Sci.4 (2012) 320
2. A. Gölcü, M. Tümer, H. Demirelli, RA.Wheatley, Inorg Chim Acta. 358, (2005) 1785
3. E.Yousif, E. Rentschler, N. Salih, J. Salimon, A. Hameed, M. Katan, J. Saudi Chem. Soc. 18 (2014) 269
4. S.A. Matar, W.H. Talib, M. S. Mustafa, M.S., Mubarak, M.A. AlDamen, Arab. J. Chem. 8 (2015) 850
5. A. Ourari, Y. Ouennoughi, D. Aggoun, M.S. Mubarak, E.M. Pasciak, D.G. Peters, Polyhedron. 67 (2014) 59
6. A.N. Srivastava, N.P. Singh, C.K. Shriwastaw, J. Serb. Chem. Soc.79 (2014) 421
7. Z. Aydin, M. Keles . Turk J Chem. 41 (2017) 89
8. E. Keskioglu, A. B.Gunduzalp, S. Cete, F. Hamurcu, B. Erk, Spectrochim. ActA.70 (2008) 634
9. I.J. Patel, S.J. Parmar, E-J. Chem. 7 (2010) 617
10. M. Hranjec, K. Starčević, S.K. Pavelić, P. Lučin, K. Pavelić, G. KarminskiZamola, Eur. J. Med. Chem. 46 (2011) 2274
11. P. Ronad, S. Dharbamalla, R. Hunshal, V. Maddi, Arch. Pharm. 341 (2008) 696
12. K.M. Khan, M. Taha, F. Naz, S. Siddiqui, S. Ali, F. Rahim, S. Perveen, I. Choudhary, Med. Chem. 8 (2012) 705
13. J.W. Schmidley, Stroke, 21 (1990) 1086
14. M.G. Hertog, E.J. Feskens, P.C. Hollman, M.B. Katan, D. Kromhout, Lancet. 342 (1993) 1007
15. N., Charef, F. Sebti, L. Arrar, M. Djarmouni, N. Boussoualim, A. Baghiani, S.Khennouf, A. Ourari, M.A. AlDamen, M.S. Mubarak, De.G. Peters, Polyhedron, 85 (2015) 450
16. N. Charef, L. Arrar, A. Ourari, R.M. Zalloum, M.S.Mubarak, Macromol. Sci. Pure and Appl. Chem. 47 (2010) 177
17. X.J. Duan, W.W. Zhang, X.M. Li, B.G. Wang, Food Chem. 95 (2006) 37
18. S. Boumerfeg, A. Baghiani, D. Messaoudi, S. Khennouf, L. Arrar, Phytother Res . 23 (2009) 283
19. B. Ates, L. Abraham, N. Ercal, Free Rad. Res. 42 (2008) 372
20. R. Re, N. Pellegrini, A. Proteggente, A. Pannala, M. Yang, C. Rice-Evans, Free Rad. Biol. Med. 26 (1999) 1231
21. M. Oyaizu, Jap. J. Nutr. 44 (1986)307
22. I. Gülçin, M. Oktay, E. Kirecci, O.I. Kufrevioglu,. Food Chem. 83 (2003) 371
23. P. Dey, T. Bhakta, J. Nat. Prod. Plant Resour. 2 (2012) 685
24. A.A. Emara, A.M. Ali, E.M. Ragab, A. A. El-Asmy, J. Coord. Chem. 61 (2008) 2968
25. Md. N .Alam, J. Bristi Nusrat, Md. Rafiquzzaman., Saudi Pharm. J. 21 (2013) 143
26. P. Arulpriya, P. Lalitha, S. Hemalatha, Der Chem. Sin. 1 (2010) 73
27. M. Leopoldini, N. Russo, M. Toscano, Food Chem. 125 (2011) 288
28. Zai-Qun Liu. QSAR. Comb. Sci.26 (2007) 488
29. J. Yang, J. Guo, J. Yuan, LWT – Food Sci. Tech. 41 (2008) 1060
30. S. Bicha, A. Amrani, O. Benaissa. F. León, D. Zama, I. Brouard, S. Benayache, A. Bentamene, F. Benayache, Der Pharm. Lett. 5 (2013) 24
31. S. Meir, J. Kanner, B. Akiri, S.P. Hadas, J. Agric. Food Chem. 43 (1995), 1813
32. J. Hirsh, M. O'Donnell, J.I. Weitz, Blood 105 (2005) 453
33. l. Sawant Ramesh,Mhaske, S. Mahesh, B. WadekarJyoti, Int. J. Pharm. Pharm. Sci.4 (2012) 320
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How to Cite
Mokhnache, K., Madoui, S., Khither, H., Soltani, E.-K., Charef, N., & Lekhmici, A. (2019). Synthesis, Characterization, Hydrolytic Cleavage, and Biological Activity Studies of 2-[(1e)-N-{2-[(2-{(Z)-[1-(2-Hydroxyphenyl)Ethylidene] Amino}Ethyl)Amino]Ethyl}Ethanimidoyl]Phenol. Journal of Drug Delivery and Therapeutics, 9(5-s), 25-29. https://doi.org/10.22270/jddt.v9i5-s.3621
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