Hydrazone Ligand and Metal Complexes: A Comprehensive Study on Synthesis, Characterization, and Urease Inhibition Potential

Main Article Content

Ghazali Hussain , Shumaila Akram , Mehreen Lateef , Asad Khan Tanoli , Nida Ali, Zahid Khan

Keywords

.

Abstract

This investigation delved into the imine group of hydrazones, elucidating its role in biological systems and emphasizing bioactivity and stable metal complexes vital for coordination chemistry. The main goal was to synthesize a hydrazone ligand, specifically 2-hydroxybenzaldehyde-N-(6-chloro-2-oxo-1,2-dihydro-3H-indol-3-ylidene), abbreviated as AG-41, along with its associated metal complexes utilizing Co(II), Ni(II), Cu(II), and Zn(II) ions.Top of Form


 The newly synthesized compounds underwent comprehensive characterization, with a focus on revealing their structures and evaluating urease inhibition activity. The research aimed to identify novel metal complexes, employing hydrazone as ligands, which were synthesized and thoroughly characterized using various analytical techniques, including FT-IR, EI-mass, elemental analysis, UV-Visible, magnetic susceptibility, and conductivity studies. It was observed that in all cases, the ligand AG-41 exhibited tridentate coordination with the metal center. The ultimate goal was to contribute to understanding the structural determinants influencing urease inhibition, laying the groundwork for innovative urease inhibitors with potential applications in medical and industrial domains. Results indicated that the metal complexes showed moderate potency, they were less effective in comparison to the hydrazone ligand. Importantly, both the ligand AG-41 and its precursor AG-40 displayed outstanding inhibitory properties when compared to the standard molecule i.e. Thiourea.

Abstract 698 | pdf Downloads 1439

References

1. Campos, K. R., Coleman, P. J., Alvarez, J. C., Dreher, S. D., Garbaccio, R. M., Terrett, N. K., Tillyer, R.D., Truppo, M.D., & Parmee, E. R. (2019). The importance of synthetic chemistry in the pharmaceutical industry. Science, 363(6424), eaat0805.
2. Kosikowska, P., & Berlicki, L. (2011). Urease inhibitors as potential drugs for gastric and urinary tract infections: a patent review. Expert opinion on therapeutic patents, 21(6), 945-957. https://doi.org/10.1517/13543776.2011.574615
3. Qin, Y., & Cabral, J. M. (2002). Review properties and applications of urease. Biocatalysis and biotransformation, 20(1), 1-14.
4. McLean, R. J., Nickel, J. C., Cheng, K. J., Costerton, J. W., & Banwell, J. G. (1988). The ecology and pathogenicity of urease-producing bacteria in the urinary tract. CRC Critical reviews in microbiology, 16(1), 37-79.
5. Krajewska, B. (2018). Urease-aided calcium carbonate mineralization for engineering applications: A review. Journal of Advanced Research, 13, 59-67.
6. Scott, D. R., Marcus, E. A., Weeks, D. L., & Sachs, G. (2002). Mechanisms of acid resistance due to the urease system of Helicobacter pylori. Gastroenterology, 123(1), 187-195. https://doi.org/10.1053/gast.2002.34218
7. Jabeen, M. (2022). A comprehensive review on analytical applications of hydrazone derivatives. Journal of the Turkish Chemical Society Section A: Chemistry, 9(3), 663-698. https://doi.org/10.18596/jotcsa.1020357
8. de Oliveira Carneiro Brum, J., França, T. C., LaPlante, S. R., & Villar, J. D. F. (2020). Synthesis and biological activity of hydrazones and derivatives: A review. Mini reviews in medicinal chemistry, 20(5), 342-368. https://doi.org/10.2174/1389557519666191014142448
9. El-Sherif, A. A., & Aljahdali, M. S. (2013). Protonation, complex-formation equilibria, and metal–ligand interaction of salicylaldehyde Schiff bases. Journal of Coordination Chemistry, 66(19), 3423-3468. https://doi.org/10.1080/00958972.2013.839027
10. Kolcu, F., Erdener, D., & Kaya, İ. (2020). A Schiff base based on triphenylamine and thiophene moieties as a fluorescent sensor for Cr (III) ions: Synthesis, characterization and fluorescent applications. Inorganica Chimica Acta, 509, 119676. https://doi.org/10.1016/j.ica.2020.119676
11. Habala, L., Devínsky, F., & Egger, A. E. (2018). Metal complexes as urease inhibitors. Journal of coordination chemistry, 71(7), 907-940. https://doi.org/10.1080/00958972.2018.1458228
12. Mohanan, K., & Murukan, B. (2005). Complexes of manganese (II), iron (II), cobalt (II), nickel (II), copper (II), and zinc (II) with a bishydrazone. Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-Metal Chemistry, 35(10), 837-844. http://dx.doi.org/10.1080/15533170500357988
13. Murukan, B., & Mohanan, K. (2006). Studies on some trivalent transition metal complexes with a bishydrazone. Journal of Saudi Chemical Society, 10(2), 261-270.
14. Murukan, B., Sindhu Kumari, B., & Mohanan, K. (2007). Synthesis, spectral, electrochemical and antibacterial studies of copper (II) complexes with isatin derived bishydrazone and different co-ligands. Journal of Coordination Chemistry, 60(15), 1607-1617.
15. Mazzei, L., Musiani, F., & Ciurli, S. (2020). The structure-based reaction mechanism of urease, a nickel dependent enzyme: Tale of a long debate. JBIC Journal of Biological Inorganic Chemistry, 25(6), 829-845.
16. Murukan, B., & Mohanan, K. (2007). Synthesis, characterization and antibacterial properties of some trivalent metal complexes with [(2-hydroxy-1-naphthaldehyde)-3-isatin]-bishydrazone. Journal of Enzyme Inhibition and Medicinal Chemistry, 22(1), 65-70. http://dx.doi.org/10.1080/14756360601027373
17. Arora, T., Devi, J., Boora, A., Taxak, B., & Rani, S. (2023). Synthesis and characterization of hydrazones and their transition metal complexes: antimicrobial, antituberculosis and antioxidant activity. Research on Chemical Intermediates, 49(11), 4819-4843.
18. Tanoli, A. K., Khan, Z., Kamal, T., Ali, M., Latif, M., & Maqsood, Z. T. (2019). Metal-based biologically active compounds: Synthesis, spectral and antioxidant studies of transition metal complexes with hydrazone derivatives. Pakistan Journal of Pharmaceutical Sciences, 32(1), 103-108.