Synthesis, Characterization and Anticancer Activity Study of New Azo Schiff Base Derivatives and its Complexes with Copper (II) and Nickel (II) Ions
Keywords:
Schiff base, azomethine, ligand, complex, anticancer
Abstract
The azo Schiff bases (L1 and L2) were synthesized and characterization on the basis their spectra of 1H-NMR, Fourier transform infrared (FTIR), as well as elemental analysis (CHN). Elemental analysis and spectral data of the ligands were found to be in a good agreement with their structures, and their complexes with Cu (II) and Ni (II) were synthesized. The anticancer activity of the syntheses compound (L1) was evaluated against MCF-7 and WRL68 cell line and it was showed a good anticancer activity.
References
1. Hussain, Z., Yousif, E., Ahmed, A., & Altaie, A. (2014). Synthesis and characterization of Schiff's bases of sulfamethoxazole. Organic and medicinal chemistry letters, 4(1), 1-4
2. Hussain, Z., Yousif, E., Ahmed, A., & Altaie, A. (2014). Synthesis and characterization of Schiff's bases of sulfamethoxazole. Organic and medicinal chemistry letters, 4(1), 1-4.
3. Safaei-Ghomi, J., Zahedi, S., & Basharnavaz, H. (2020). Synthesis and Characterization of Ionic Liquid Supported on Fe3O4 Nanoparticles and a DFT Study of 1, 3-Dipolar Cycloaddition for the Synthesis of Isoxazolidines in the Presence of Ionic Liquid-Fe3O4. Polycyclic Aromatic Compounds, 40(3), 574-584.
4. Hania, M. M. (2009). Synthesis of some imines and investigation of their biological activity. E-Journal of Chemistry, 6(3), 629-632.
5. Canpolat, E., & Kaya, M. (2005). Studies on mononuclear chelates derived from substituted Schiff Base ligands: Synthesis and characterization of a new 5-methoxysalicyliden-p-aminoacetophenoneoxime and its complexes with Co (II), Ni (II), Cu (II), and Zn (II). Russian Journal of Coordination Chemistry, 31, 790-794
6. Samanta, B., Chakraborty, J., Choudhury, C. R., Dey, S. K., Dey, D. K., Batten, S. R.,... & Mitra, S. (2007). New Cu (II) complexes with polydentate chelating Schiff base ligands: Synthesis, structures, characterisations and biochemical activity studies. Structural Chemistry, 18, 33-41
7. He, S. X., Yu, H. H., Huang, C., Chen, D. M., & Zhu, B. X. (2023). Metallomacrocycle or 1D chain: Synthesis, structures, and antifungal activities of zinc (II) and silver (I) complexes based on two reduced Schiff base ligands. Journal of Molecular Structure, 1271,136073.
8. Dong, Y., Li, M., Hao, Y., Feng, Y., Ren, Y., & Ma, H. (2023). Antifungal Activity, Structure‐Activity Relationship and Molecular Docking Studies of 1, 2, 4‐Triazole Schiff Base Derivatives. Chemistry & Biodiversity, 20(3), e202201107.
9. Devi, P., Singh, K., & Kubavat, B. (2023). Synthesis, spectroscopic, quantum, thermal and kinetics, antibacterial and antifungal studies: Novel Schiff base 5-methyl-3-((5-bromosalicylidene) amino)-pyrazole and its transition metal complexes. Results in Chemistry, 5, 100813.
10. Mekky, A. H., Mohammad, Z. A. A., & Auribi, S. M. (2012). Synthesis and biological activity of monocyclic spiro azetidine-2-one. J. Educ. Pure Sci, 2(1), 67-74 Tople, M. S., Patel, N. B., Patel, P. P., Purohit, A. C., Ahmad, I., & Patel, H. (2023). An in silico-in vitro antimalarial and antimicrobial investigation of newer 7-chloroquinoline based Schiff-bases. Journal of Molecular Structure, 1271, 134016.
11. AL-Rubaie, L. A. (2014). Synthesis and Theoretical Study of new Schiff base derivatives. University of Thi-Qar Journal of Science, 4(3), 119-122.
12. Gueye, M. N., Dieng, M., Thiam, I. E., Lo, D., Barry, A. H., Gaye, M., & Retailleau, P. (2017). Lanthanide (III) complexes with tridentate Schiff base ligand, antioxidant activity and X-ray crystal structures of the Nd (III) and Sm (III) complexes. South African Journal of Chemistry, 70, 8-15.
13. Hosny, S., Ragab, M. S., & Abd El-Baki, R. F. (2023). Synthesis of a new sulfadimidine Schiff base and their nano complexes as potential anti-COVID-19 and anti-cancer activity. Scientific Reports, 13(1), 1502.
14. Abdel-Rahman, L. H., Abdelghani, A. A., AlObaid, A. A., El-ezz, D. A., Warad, I., Shehata, M. R., & Abdalla, E. M. (2023). Novel Bromo and methoxy substituted Schiff base complexes of Mn (II), Fe (III), and Cr (III) for anticancer, antimicrobial, docking, and ADMET studies. Scientific reports, 13(1), 3199.
15. Mostafa, M. A., Ismail, M. M., Morsy, J. M., Hassanin, H. M., & Abdelrazek, M. M. (2023). Synthesis, characterization, anticancer, and antioxidant activities of chitosan Schiff bases bearing quinolinone or pyranoquinolinone and their silver nanoparticles derivatives. Polymer Bulletin, 80(4), 4035-4059.
16. Alorini, T., Daoud, I., Al-Hakimi, A. N., Alminderej, F., & Albadri, A. E. (2023). An experimental and theoretical investigation of antimicrobial and anticancer properties of some new Schiff base complexes. Research on Chemical Intermediates, 49(4), 1701-1730.
17. Talebi, A., Salehi, M., Khaleghian, A., & Kubicki, M. (2023). Evaluation of anticancer activities, apoptosis, molecular docking, and antioxidant studies of new Ni (II), VO (IV), Cu (II) and Co (III) Schiff base complexes. Inorganica Chimica Acta, 546, 121296.
18. Kaushik, S., Paliwal, S. K., Iyer, M. R., & Patil, V. M. (2023). Promising Schiff bases in antiviral drug design and discovery. Medicinal Chemistry Research, 32, pages 1063–1076.
19. Al-Wahaibi, L. H., El-Sheref, E. M., Hammouda, M. M., & Youssif, B. G. (2023). One-Pot Synthesis of 1-Thia-4-azaspiro [4.4/5] alkan-3-ones via Schiff Base: Design, Synthesis, and Apoptotic Antiproliferative Properties of Dual EGFR/BRAFV600E Inhibitors. Pharmaceuticals, 16(3), 467
20. El-Lateef, A., Hany, M., Elbastawesy, M. A., Abdelghani Ibrahim, T. M., Khalaf, M. M., Gouda, M.,... & Morcoss, M. M. (2023). Design, Synthesis, Docking Study, and Antiproliferative Evaluation of Novel Schiff Base–Benzimidazole Hybrids with VEGFR-2 Inhibitory Activity. Molecules, 28(2), 481. x
21. Alyamani, N. M. (2023). New Schiff Base–TMB Hybrids: Design, Synthesis and Antiproliferative Investigation as Potential Anticancer Agents. Symmetry, 15(3), 609.
22. Kumar, B., Devi, J., & Manuja, A. (2023). Synthesis, structure elucidation, antioxidant, antimicrobial, anti-inflammatory and molecular docking studies of transition metal (II) complexes derived from heterocyclic Schiff base ligands. Research on Chemical Intermediates, 49(6), 2455-2493.
23. Gung, B. W., & Taylor, R. T. (2004). Parallel combinatorial synthesis of azo dyes: a combinatorial experiment suitable for undergraduate laboratories. Journal of chemical education, 81(11), 1630.
24. Li, X., & Zhang, Y. M. (2006). Study on the reactions of azo compounds with acyl halides mediated by Sm/TiCl 4. Journal of Zhejiang University SCIENCE B, 7, 198-201.
25. El-Sherif, A. A., Shehata, M. R., Shoukry, M. M., & Barakat, M. H. (2012). Synthesis, characterization, equilibrium study and biological activity of Cu (II), Ni (II) and Co (II) complexes of polydentate Schiff base ligand. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 96, 889-897.
26. Mohammed, K. F., & Hasan, H. A. (2022). Synthesis, chemical and biological activity Studies of azo-Schiff base ligand and its metal complexes. Chem Methodol, 12, 905-913.
27. Tapabashi, N. O., Taha, N. I., & El-Subeyhi, M. N. (2021). Synthesis and Characterization of Some New Azo-Schiff Bases as Energy Rich Candidate Compounds Derived from 1, 5-Diaminoanthraquinone by Fusion Method. Kirkuk University Journal-Scientific Studies, 16(2), 51-63.
28. Prakash, A., Singh, B. Κ., Rajour, H. Κ., & Bhojak, N. (2010). Synthesis, Characterization and Bioactivities of New Schiff Bases with Main Group Metal Ions. Main Group Metal Chemistry, 33(4-5), 183-200.
29. Khalil, E., Mahmoud, W., & Mohamed, G. (2021). Synthesis, spectral, thermal and biological studies of some transition and inner transition Schiff base metal complexes. Egyptian Journal of Chemistry, 64(7), 3555-3571.
2. Hussain, Z., Yousif, E., Ahmed, A., & Altaie, A. (2014). Synthesis and characterization of Schiff's bases of sulfamethoxazole. Organic and medicinal chemistry letters, 4(1), 1-4.
3. Safaei-Ghomi, J., Zahedi, S., & Basharnavaz, H. (2020). Synthesis and Characterization of Ionic Liquid Supported on Fe3O4 Nanoparticles and a DFT Study of 1, 3-Dipolar Cycloaddition for the Synthesis of Isoxazolidines in the Presence of Ionic Liquid-Fe3O4. Polycyclic Aromatic Compounds, 40(3), 574-584.
4. Hania, M. M. (2009). Synthesis of some imines and investigation of their biological activity. E-Journal of Chemistry, 6(3), 629-632.
5. Canpolat, E., & Kaya, M. (2005). Studies on mononuclear chelates derived from substituted Schiff Base ligands: Synthesis and characterization of a new 5-methoxysalicyliden-p-aminoacetophenoneoxime and its complexes with Co (II), Ni (II), Cu (II), and Zn (II). Russian Journal of Coordination Chemistry, 31, 790-794
6. Samanta, B., Chakraborty, J., Choudhury, C. R., Dey, S. K., Dey, D. K., Batten, S. R.,... & Mitra, S. (2007). New Cu (II) complexes with polydentate chelating Schiff base ligands: Synthesis, structures, characterisations and biochemical activity studies. Structural Chemistry, 18, 33-41
7. He, S. X., Yu, H. H., Huang, C., Chen, D. M., & Zhu, B. X. (2023). Metallomacrocycle or 1D chain: Synthesis, structures, and antifungal activities of zinc (II) and silver (I) complexes based on two reduced Schiff base ligands. Journal of Molecular Structure, 1271,136073.
8. Dong, Y., Li, M., Hao, Y., Feng, Y., Ren, Y., & Ma, H. (2023). Antifungal Activity, Structure‐Activity Relationship and Molecular Docking Studies of 1, 2, 4‐Triazole Schiff Base Derivatives. Chemistry & Biodiversity, 20(3), e202201107.
9. Devi, P., Singh, K., & Kubavat, B. (2023). Synthesis, spectroscopic, quantum, thermal and kinetics, antibacterial and antifungal studies: Novel Schiff base 5-methyl-3-((5-bromosalicylidene) amino)-pyrazole and its transition metal complexes. Results in Chemistry, 5, 100813.
10. Mekky, A. H., Mohammad, Z. A. A., & Auribi, S. M. (2012). Synthesis and biological activity of monocyclic spiro azetidine-2-one. J. Educ. Pure Sci, 2(1), 67-74 Tople, M. S., Patel, N. B., Patel, P. P., Purohit, A. C., Ahmad, I., & Patel, H. (2023). An in silico-in vitro antimalarial and antimicrobial investigation of newer 7-chloroquinoline based Schiff-bases. Journal of Molecular Structure, 1271, 134016.
11. AL-Rubaie, L. A. (2014). Synthesis and Theoretical Study of new Schiff base derivatives. University of Thi-Qar Journal of Science, 4(3), 119-122.
12. Gueye, M. N., Dieng, M., Thiam, I. E., Lo, D., Barry, A. H., Gaye, M., & Retailleau, P. (2017). Lanthanide (III) complexes with tridentate Schiff base ligand, antioxidant activity and X-ray crystal structures of the Nd (III) and Sm (III) complexes. South African Journal of Chemistry, 70, 8-15.
13. Hosny, S., Ragab, M. S., & Abd El-Baki, R. F. (2023). Synthesis of a new sulfadimidine Schiff base and their nano complexes as potential anti-COVID-19 and anti-cancer activity. Scientific Reports, 13(1), 1502.
14. Abdel-Rahman, L. H., Abdelghani, A. A., AlObaid, A. A., El-ezz, D. A., Warad, I., Shehata, M. R., & Abdalla, E. M. (2023). Novel Bromo and methoxy substituted Schiff base complexes of Mn (II), Fe (III), and Cr (III) for anticancer, antimicrobial, docking, and ADMET studies. Scientific reports, 13(1), 3199.
15. Mostafa, M. A., Ismail, M. M., Morsy, J. M., Hassanin, H. M., & Abdelrazek, M. M. (2023). Synthesis, characterization, anticancer, and antioxidant activities of chitosan Schiff bases bearing quinolinone or pyranoquinolinone and their silver nanoparticles derivatives. Polymer Bulletin, 80(4), 4035-4059.
16. Alorini, T., Daoud, I., Al-Hakimi, A. N., Alminderej, F., & Albadri, A. E. (2023). An experimental and theoretical investigation of antimicrobial and anticancer properties of some new Schiff base complexes. Research on Chemical Intermediates, 49(4), 1701-1730.
17. Talebi, A., Salehi, M., Khaleghian, A., & Kubicki, M. (2023). Evaluation of anticancer activities, apoptosis, molecular docking, and antioxidant studies of new Ni (II), VO (IV), Cu (II) and Co (III) Schiff base complexes. Inorganica Chimica Acta, 546, 121296.
18. Kaushik, S., Paliwal, S. K., Iyer, M. R., & Patil, V. M. (2023). Promising Schiff bases in antiviral drug design and discovery. Medicinal Chemistry Research, 32, pages 1063–1076.
19. Al-Wahaibi, L. H., El-Sheref, E. M., Hammouda, M. M., & Youssif, B. G. (2023). One-Pot Synthesis of 1-Thia-4-azaspiro [4.4/5] alkan-3-ones via Schiff Base: Design, Synthesis, and Apoptotic Antiproliferative Properties of Dual EGFR/BRAFV600E Inhibitors. Pharmaceuticals, 16(3), 467
20. El-Lateef, A., Hany, M., Elbastawesy, M. A., Abdelghani Ibrahim, T. M., Khalaf, M. M., Gouda, M.,... & Morcoss, M. M. (2023). Design, Synthesis, Docking Study, and Antiproliferative Evaluation of Novel Schiff Base–Benzimidazole Hybrids with VEGFR-2 Inhibitory Activity. Molecules, 28(2), 481. x
21. Alyamani, N. M. (2023). New Schiff Base–TMB Hybrids: Design, Synthesis and Antiproliferative Investigation as Potential Anticancer Agents. Symmetry, 15(3), 609.
22. Kumar, B., Devi, J., & Manuja, A. (2023). Synthesis, structure elucidation, antioxidant, antimicrobial, anti-inflammatory and molecular docking studies of transition metal (II) complexes derived from heterocyclic Schiff base ligands. Research on Chemical Intermediates, 49(6), 2455-2493.
23. Gung, B. W., & Taylor, R. T. (2004). Parallel combinatorial synthesis of azo dyes: a combinatorial experiment suitable for undergraduate laboratories. Journal of chemical education, 81(11), 1630.
24. Li, X., & Zhang, Y. M. (2006). Study on the reactions of azo compounds with acyl halides mediated by Sm/TiCl 4. Journal of Zhejiang University SCIENCE B, 7, 198-201.
25. El-Sherif, A. A., Shehata, M. R., Shoukry, M. M., & Barakat, M. H. (2012). Synthesis, characterization, equilibrium study and biological activity of Cu (II), Ni (II) and Co (II) complexes of polydentate Schiff base ligand. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 96, 889-897.
26. Mohammed, K. F., & Hasan, H. A. (2022). Synthesis, chemical and biological activity Studies of azo-Schiff base ligand and its metal complexes. Chem Methodol, 12, 905-913.
27. Tapabashi, N. O., Taha, N. I., & El-Subeyhi, M. N. (2021). Synthesis and Characterization of Some New Azo-Schiff Bases as Energy Rich Candidate Compounds Derived from 1, 5-Diaminoanthraquinone by Fusion Method. Kirkuk University Journal-Scientific Studies, 16(2), 51-63.
28. Prakash, A., Singh, B. Κ., Rajour, H. Κ., & Bhojak, N. (2010). Synthesis, Characterization and Bioactivities of New Schiff Bases with Main Group Metal Ions. Main Group Metal Chemistry, 33(4-5), 183-200.
29. Khalil, E., Mahmoud, W., & Mohamed, G. (2021). Synthesis, spectral, thermal and biological studies of some transition and inner transition Schiff base metal complexes. Egyptian Journal of Chemistry, 64(7), 3555-3571.
Published
2023-09-30
How to Cite
Abid, S. H., & Mahdi, H. A. (2023). Synthesis, Characterization and Anticancer Activity Study of New Azo Schiff Base Derivatives and its Complexes with Copper (II) and Nickel (II) Ions. Central Asian Journal of Medical and Natural Science, 4(5), 354-365. Retrieved from https://cajmns.centralasianstudies.org/index.php/CAJMNS/article/view/1832
Section
Articles
