Synthesis, Characterization, and Bioactivity Studies of the Schiff Base Ligand and its Zinc(II) Complex

Muhammad Salih, Nabaz A. (2024) Synthesis, Characterization, and Bioactivity Studies of the Schiff Base Ligand and its Zinc(II) Complex. ARO-THE SCIENTIFIC JOURNAL OF KOYA UNIVERSITY, 12 (1). pp. 108-114. ISSN 2410-9355

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Abstract

One of the largest concerns to global health in recent decades has been identified as the growth of bacteria resistance to antibiotics. The Schiff base (SBs) and the zinc(II) SBs complex compounds category have attracted a lot of interest because of their function in chemical syntheses and their potential for bioactive and pharmacological effects. The present study includes the synthesis of various SBs with different substituents. Equimolar mixtures of benzaldehyde derivatives (1, 2) and aniline derivatives (3, 4) are used to carry out a series of condensation reactions to get compounds (5-7). By stoichiometrically combining Zn (II) acetate and ZnCl2 separately with the SBs ligand (7) in ethanol, it has been possible to prepare the SBs zinc(II) complex (8). The structure of the ligand and its metal complex are analyzed using (Fourier transform infrared spectroscopy, 1H-NMR, 13C-NMR) spectroscopy, scanning electron microscopy, and liquid chromatography–mass spectrometry. Moreover, the synthesized compounds are verified in vitro against Escherichia coli Gram negative, Staphylococcus aureus Gram positive, and fungi (Candida albicans). Compounds (5, 7, and 8) indicated significant growth inhibition against E. coli Gram negative and fungi (C. albicans) with different inhibition zones starting from 7 to 17.5 mm.

Item Type: Article
Additional Information: Bazhina, E.S., Bovkunova, A.A., Shmelev, M.A., Korlyukov, A.A., Pavlov, A.A., Hochvaldov, L., Kopel, P., Eremenko, L., and Kiskin, M.A., 2023. Inorganica chimica acta zinc(II) and copper(II) complexes with N-substituted imines derived from 4-amino-1, 2, 4-triazole : Synthesis, crystal structure, and biological activity. Inorganica Chimica Acta, 547, p.121359. DOI: https://doi.org/10.1016/j.ica.2022.121359 Bekdemir, Y., and Efil, K., 2014. Microwave assisted solvent-free synthesis of some imine derivatives. Organic Chemistry International, 2014, pp.816487. DOI: https://doi.org/10.1155/2014/816487 Bendale, A.R., Bhatt, R., and Narkhede, S., 2011. Scholars research library. Der Pharma Chemica, 3(2), pp.34-38. Devidas, S.M., Quadri, S.H., Kamble, S.A., Syed, F.M., and Vyavhare, D.Y., 2011. Novel one-pot synthesis of Schiff base compounds derived from different Diamine and aromatic aldehyde catalyzed by P2 O 5/SiO2 under free-solvent condition at room temperature. Journal of Chemical and Pharmaceutical Research, 3, pp. 489-495. Gopalakrishnan, M., Sureshkumar, P., Kanagarajan, V., and Thanusu, J., 2007. New environmentally-friendly solvent-free synthesis of imines using calcium oxide under microwave irradiation. Research on Chemical Intermediates, 33(6), pp. 541-548. DOI: https://doi.org/10.1163/156856707782565822 Hajiashrafi, T., Zekriazadeh, R., and Kubicki, M., 2020. Synthesis, characterization, and crystal structure analysis of group IIB coordination compounds containing N,N’-bidentate chelating Schiff-base ligand. Journal of Coordination Chemistry, 73(20-22), pp.3044-3061. DOI: https://doi.org/10.1080/00958972.2020.1830072 Jaber, Z.A., 2023. Synthesis, Theoretical study, and Biological evaluation of some metal ions with ligand “Methyl-6-[2-(4-hydroxyphenyl) -2-((1-phenylethylidene) amino) acetamido]-2,2-dimethyl-5-oxo-1-thia-4-azabicyclo [3.2.0] heptane-3 carboxyylate. Baghdad Science Journal, 20, pp.102-113. DOI: https://doi.org/10.21123/bsj.2022.6359 Journal, B.S., and Al-Daffaay, R.K., 2022. Preparation-and spectroscopic characterization of transition metal complexes with schiff base 2-[1-(1H-indol 3-yl) ethylimino)methyl. Baghdad Science Journal, 19, pp.1036-1044. DOI: https://doi.org/10.21123/bsj.2022.6162 Kolapwar, B.G., 2017. Study of schiff base compounds and its derivatives. Anveshana’s International Journal of Research in Pharmacy and Life Sciences, 2(1), pp.15-18. Liang, X., Zhao, X., Guo, A., Wang, X., Rong, M., Chang, L., Sun, Z., and Jin, X., 2023. Synthesis, crystal structure and antibacterial activity of zinc(II) complexes with Schiff bases derived from 5-fluorosalicylaldehyde. Journal of Coordination Chemistry, 76(2), pp.307-321. DOI: https://doi.org/10.1080/00958972.2023.2170795 Mahdi, A.S., and Ismail, A.H., 2022. New tetra-dentate schiff base ligand N2O2 and its complexes with some of metal ions : Preparation, identification, and studying their enzymatic and biological activities. Baghdad Science Journal, 19, pp.155-167. DOI: https://doi.org/10.21123/bsj.2022.19.1.0155 Mathews, N.A., Begum, P.M.S., and Kurup, M.R.P., 2020. Synthesis, characterization, biological screening and molecular docking of Zn(II) and Cu(II) complexes of 3,5-dichlorosalicylaldehyde-N4-cyclohexylthiosemicarbazone. Applied Organometallic Chemistry, 34(1), pp.1-14. DOI: https://doi.org/10.1002/aoc.5294 Murhekar, M.M., and Khadsan, R.E., 2011. Synthesis of schiff bases by organic free solvent method. Journal of Chemical and Pharmaceutical Research, 3(6), pp.846-849. Muzammil, K., Trivedi, P., and Khetani, D., 2015. Synthesis and characterization of Schiff base m-nitro aniline and their complexes. Research Journal of Chemical Sciences, 5(5), pp. 52-55. Omidi, S., and Kakanejadifard, A., 2020. A review on biological activities of Schiff base, hydrazone, and oxime derivatives of curcumin. RSC Advances, 10(50), pp.30186-30202. DOI: https://doi.org/10.1039/D0RA05720G Pinchaipat, B., Khudkham, T., Wongsuwan, S., and Chotima, R., 2021. The novel zinc(II) complex with dibromo substituted Schiff base and its biological activity. Materials Letters, 293, p.129749. DOI: https://doi.org/10.1016/j.matlet.2021.129749 Pooja, B., Lalit, M., Richa, G., and Pramanik, T., 2018. Microwave assisted green synthesis of Schiff bases in lemon juice medium. Research Journal of Chemistry and Environment, 22(8), pp. 19-23. Poole, K., 2017. At the nexus of antibiotics and metals: The impact of Cu and Zn on antibiotic activity and resistance. Trends in Microbiology, 25(10), pp.820-832. DOI: https://doi.org/10.1016/j.tim.2017.04.010 Sadia, M., Khan, J., Naz, R., Zahoor, M., Wadood Ali Shah, S., Ullah, R., Naz, S., Bari, A., Majid Mahmood, H., Saeed Ali, S., Ansari, S.A., and Sohaib, M., 2021. Schiff base ligand L synthesis and its evaluation as anticancer and antidepressant agent. Journal of King Saud University-Science, 33(2), p.101331. DOI: https://doi.org/10.1016/j.jksus.2020.101331 Shah, S.S., Shah, D., Khan, I., Ahmad, S., Ali, U., and Rahman, A.U., 2020. Synthesis and antioxidant activities of schiff bases and their complexes: An updated review. Biointerface Research in Applied Chemistry, 10(6), pp.6936-6963. DOI: https://doi.org/10.33263/BRIAC106.69366963 Shammout, M.J.A., Jazzazi, T.M.A., Alomari, M., Daoud, S., and Talib, W.H., 2021. Synthesis, computational, anticancerous and antiproliferative effects of some copper, manganese and zinc complexes with ligands derived from symmetrical 2,2’-diamino-4,4’-dimethyl-1,1’-biphenyl-salicylaldehyde. Polish Journal of Chemical Technology, 10(4), pp.7-15. DOI: https://doi.org/10.2478/pjct-2021-0002 Slassi, S., El-Ghayoury, A., Aarjane, M., Yamni, K., and Amine, A., 2020. New copper(II) and zinc(II) complexes based on azo schiff base ligand: Synthesis, crystal structure, photoisomerization study and antibacterial activity. Applied Organometallic Chemistry, 34(4), pp.1-10. DOI: https://doi.org/10.1002/aoc.5503 Vhanale, B.T., Deshmukh, N.J., and Shinde, A.T., 2019. Synthesis, characterization, spectroscopic studies and biological evaluation of schiff bases derived from 1-hydroxy-2-acetonapthanone. Heliyon, 5(11), p.e02774. DOI: https://doi.org/10.1016/j.heliyon.2019.e02774 Yousif, E., Majeed, A., Al-Sammarrae, K., Salih, N., Salimon, J., and Abdullah, B., 2017. Metal complexes of schiff base: Preparation, characterization and antibacterial activity. Arabian Journal of Chemistry, 10, pp.S1639-S1644. DOI: https://doi.org/10.1016/j.arabjc.2013.06.006
Uncontrolled Keywords: Bioactive studies, Condensation reaction, Microorganism, Schiff base, Zinc(II) complex
Subjects: Q Science > QD Chemistry
Divisions: ARO-The Scientific Journal of Koya University > VOL 12, NO 1 (2024)
Depositing User: Dr Salah Ismaeel Yahya
Date Deposited: 02 Sep 2024 06:58
Last Modified: 02 Sep 2024 06:58
URI: http://eprints.koyauniversity.org/id/eprint/476

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