Synthesis of Manganese(II), Iron(III), and Vanadium(IV) Complexes with New Schiff Bases and their Spectroscopic and Thermal Studies and Evaluation of their Antimicrobial Activity

Year 2024, , 101 - 112, 04.02.2024

Sinan Al-bayati , Sarab Alazawi , Sadeem Al-barody , Anaam Majeed , Rehab Alhassani

https://doi.org/10.18596/jotcsa.1250844

An Erratum to this article was published on May 15, 2024. https://dergipark.org.tr/en/pub/jotcsa/issue/82621/1484401

Abstract

Heterocyclic 3-acetyl coumarin with hydrazide derivatives and their metal complexes are a substantial family of pharmaceutical drugs used to treat infection, anti-inflammatory issues, diabetes, and neurological disorders in the field of medicinal chemistry. Cyclization of 5- floro-2-furaldehyde, ethyl acetoacetate, and urea or thiourea by LaCl3.7H2O, addition of hydrazine to form amine derivatives were performed, and respective Schiff base derivatives (L1, L2) were produced by adding acetyl coumarin in an ethanolic solution at ambient temperature. New ligands and its complexes of the V (IV), Fe (III) and Mn (II) ions were characterized using (FT-IR, UV, MS) and nuclear magnetic resonance (1H-NMR) as well as elemental analysis (CHN). The synthesized complexes chelate with ligands L1, L2 via (N, O2) atoms. The structural geometry of the complexes was illustrated in the solid phase using FT-IR and UV-VIS spectroscopy, elemental analysis (CHNS), and flame atomic absorption, in addition to magnetic susceptibility and conductivity measurement. The antibacterial activity of the newly prepared ligands and their metal complexes was evaluated against Pseudonomous aerugionosa as a gram negative and Bacillus subtilis as a gram positive microorganism. Moreover, the antifungal activity against two fungi Aspergillus flavus, and Saccharomyces cerevisiae was studied for all compounds. The coordinated ligands significantly increased their bactericidal and fungicidal action compared to the free ligands, which did not exhibit any activity against the selected fungal and bacterial strains. The results focused on the synergetic relationship between the metal ion and the ligand, in addition to the structural variation.

Keywords

biological activity, metal complexes, coumarin, hydrazide derivatives, 5-fluorofuran, schiff bases

Thanks

Great thanks from the authors to the Department of Chemistry, College of Science, Mustansiriyah University, for providing facilities and laboratories.

References

• 1. Ahmad F, Idris MHS, Adib AM. Synthesis and characterization some flavonoids derivatives [Internet]. Research Vote: 75148. Malaysia; 2006 [cited 2023 Nov 6]. Available from: <URL>.
• 2. Alajrawy OI. Synthesis and characterization of vanadium (IV) and (V) complexes with 2, 2`-bipyridine ligand. 2019;
• 3. Patil SA, Kandathil V, Sobha A, Somappa SB, Feldman MR, Bugarin A, et al. Comprehensive Review on Medicinal Applications of Coumarin-Derived Imine–Metal Complexes. Molecules [Internet]. 2022 Aug 16;27(16):5220. Available from: <URL>.
• 4. Hamid SJ, Salih T. Design, Synthesis, and Anti-Inflammatory Activity of Some Coumarin Schiff Base Derivatives: In silico and in vitro Study. Drug Des Devel Ther [Internet]. 2022 Jul;16:2275–88. Available from: <URL>.
• 5. Melagraki G, Afantitis A, Igglessi-Markopoulou O, Detsi A, Koufaki M, Kontogiorgis C, et al. Synthesis and evaluation of the antioxidant and anti-inflammatory activity of novel coumarin-3-aminoamides and their alpha-lipoic acid adducts. Eur J Med Chem [Internet]. 2009 Jul 1;44(7):3020–6. Available from: <URL>.
• 6. Sahoo S, Himanshu D, Sahoo B, Sahoo SS, Shukla S, Nandy S, et al. Synthesis of novel coumarin derivatives and its biological evaluations. Eur J Exp Biol [Internet]. 2012;2(4):899–908. Available from: <URL>.
• 7. Bader AT, Al-qasii NAR, Shntaif AH, El Marouani M, AL Majidi MIH, Trif L, et al. Synthesis, Structural Analysis and Thermal Behavior of New 1,2,4-Triazole Derivative and Its Transition Metal Complexes. Indones J Chem [Internet]. 2022 Dec 28;22(1):223–32. Available from: <URL>.
• 8. Shaban S, baghi hamza, Shafek S, zein nabila, Aiad I, Omran M. Synthesis and characterization of new 1,2,4-triazole anticancer scaffold derivatives: In Vitro study. Egypt J Chem [Internet]. 2021 Mar 31;64(8):4005–15. Available from: <URL>.
• 9. Ndahi NP, Garba H, Waziri I, Osunlaja AA, Putaya HAN. Complexes of Mn(II) and Fe (III) with Schiff bases Derived from Trimethoprim with Salicyldehyde and Benzaldehyde as Potential Antimicrobial Agents. Niger J Pharm Biomed Res [Internet]. 2018;3(1):53–9. Available from: <URL>.
• 10. Al-Warhi T, Sabt A, Elkaeed EB, Eldehna WM. Recent advancements of coumarin-based anticancer agents: An up-to-date review. Bioorg Chem [Internet]. 2020 Oct 1;103:104163. Available from: <URL>.
• 11. Sumrra SH, Ramzan S, Mustafa G, Ibrahim M, Mughal EU, Nadeem MA, et al. Complexes of Imino-1,2,4-triazole Derivative with Transition Metals: Synthesis and Antibacterial Study. Russ J Gen Chem [Internet]. 2018 Aug 16;88(8):1707–11. Available from: <URL>.
• 12. Bagihalli GB, Avaji PG, Patil SA, Badami PS. Synthesis, spectral characterization, in vitro antibacterial, antifungal and cytotoxic activities of Co(II), Ni(II) and Cu(II) complexes with 1,2,4-triazole Schiff bases. Eur J Med Chem [Internet]. 2008 Dec 1;43(12):2639–49. Available from: <URL>.
• 13. Singh MS, Chowdhury S, Koley S. Advances of azide-alkyne cycloaddition-click chemistry over the recent decade. Tetrahedron. 2016 Sep;72(35):5257–83.
• 14. Ismail AH, Al-Bairmani HK, Abbas ZS, Rheima AM. Synthesis, Characterization, Spectroscopic and Biological Studies of Zn(II), Mn(II) and Fe(II) Theophylline Complexes in Nanoscale. Nano Biomed Eng [Internet]. 2020 Sep 18;12(3):253–61. Available from: <URL>.
• 15. Knittl ET, Abou-Hussein AA, Linert W. Syntheses, characterization, and biological activity of novel mono- and binuclear transition metal complexes with a hydrazone Schiff base derived from a coumarin derivative and oxalyldihydrazine. Monatshefte für Chemie - Chem Mon [Internet]. 2018 Feb 27;149(2):431–43. Available from: <URL>.
• 16. Shukla SN, Gaur P, Raidas ML, Chaurasia B, Bagri SS. Novel NNO pincer type Schiff base ligand and its complexes of Fe(IIl), Co(II) and Ni(II): Synthesis, spectroscopic characterization, DFT, antibacterial and anticorrosion study. J Mol Struct [Internet]. 2021 Sep 15;1240:130582. Available from: <URL>.
• 17. Patil SA, Prabhakara CT, Halasangi BM, Toragalmath SS, Badami PS. DNA cleavage, antibacterial, antifungal and anthelmintic studies of Co(II), Ni(II) and Cu(II) complexes of coumarin Schiff bases: Synthesis and spectral approach. Spectrochim Acta Part A Mol Biomol Spectrosc [Internet]. 2015 Feb 25;137:641–51. Available from: <URL>.
• 18. Al-Zaidi BH, Hasson MM, Ismail AH. New complexes of chelating Schiff base: Synthesis, spectral investigation, antimicrobial, and thermal behavior studies. J Appl Pharm Sci [Internet]. 2019 Apr;9(4):45–57. Available from: <URL>.
• 19. Priya B, Kumar A, Sharma N. Synthesis, Characterisation, and Biological Properties of Oxidovanadium(IV) 3,5-Dinitrosalicylhydroxamate Complexes. Aust J Chem [Internet]. 2020;73(1):61–72. Available from: <URL>.
• 20. Al-Hasani RAM, Rasheed AM, AL-bayati SM. Synthesis, Characterization and Bioactivities of V(III), Cr(III), Fe(III), Rh(III) and Al(III) Complexes with Bis(Salicylaldehyde)MalonylDihydrazone and 8-HydroxyQuinoline as Mixed Ligands. Iraqi Natl J Chem [Internet]. 2016;16(3):127–42. Available from: <URL>.
• 21. Akkasali R, Patil N, Angadi SD. Synthesis, Characterization and Microbial Activities of Metal Complexes with Coumarine Derivatives. Rasayan J Chem [Internet]. 2009;2(1):81–6. Available from: <URL>.
• 22. Yaul SR, Yaul AR, Pethe GB, Aswar AS. Synthesis and characterization of transition metal complexes with N, O-chelating hydrazone Schiff base ligand. Am J Sci Res [Internet]. 2009;4(4):229–34. Available from: <URL>.
• 23. Martínez RF, Ávalos M, Babiano R, Cintas P, Light ME, Jiménez JL, et al. Hydrazones from hydroxy naphthaldehydes and N-aminoheterocycles: structure and stereodynamics. Tetrahedron [Internet]. 2011 Mar 18;67(11):2025–34. Available from: <URL>.
• 24. Golcu A, Tumer M, Demirelli H, Wheatley RA. Cd(II) and Cu(II) complexes of polydentate Schiff base ligands: synthesis, characterization, properties and biological activity. Inorganica Chim Acta [Internet]. 2005 Mar 30;358(6):1785–97. Available from: <URL>.
• 25. Puckett CA, Ernst RJ, Barton JK. Exploring the cellular accumulation of metal complexes. Dalt Trans [Internet]. 2010 Jan 19;39(5):1159–70. Available from: <URL>.
• 26. Alazawi SM, Rasheed AM, Al-Bay SM, Abed AH. Synthesis, Spectral and Biological Studies of New 2-amino-3-cyanopyridine Derivatives and Their Transition Metals Complexes. Egypt J Chem [Internet]. 2021 Mar 15;64(6):2937–44. Available from: <URL>.
• 27. Al-Bayati S, Rasheed A, Zuhair E, Abid K, Khamis W. Synthesis and Spectroscopic Studies of New Alkoxy Schiff Base Complexes Based on Coumarin Moiety. Am J Chem [Internet]. 2018;8(1):1–7. Available from: <URL>.