Citation: Oladeji S. Olatunde, Ikhile I. Monisola, Mamo Messai, Ndungu G. Patrick, Ndinteh T. Derek. Synthesis, Characterization and Antimicrobial Screening of Various Ferrocenyl Schiff Bases against Gram-positive and Gram-negative Bacteria[J]. Chinese Journal of Inorganic Chemistry, ;2022, 38(4): 705-715. doi: 10.11862/CJIC.2022.065 shu

Synthesis, Characterization and Antimicrobial Screening of Various Ferrocenyl Schiff Bases against Gram-positive and Gram-negative Bacteria

Department of Chemical Sciences, Faculty of Science, University of Johannesburg, Johannesburg, South Africa

Corresponding author: Ikhile I. Monisola, miikhile@gmail.com Ndinteh T. Derek, dndinteh@uj.ac.za
Received Date: 10 May 2021
Revised Date: 24 November 2021

Figures(4)

Ten ferrocenyl Schiff bases 1-10 were synthesized and characterized using UV-Vis spectroscopy, FT-IR, elemental analysis, ¹H and ¹³C NMR spectroscopy. The synthesized compounds were evaluated against 11 bacteria strains (Bacillus subtilis ATCC19659, Klebsiella aerogenes ATCC13882, Enterococcus faecalis ATCC13047, Myco- bacterium smegmatis MC2155, Staphylococcus epidermidis ATCC14990, Staphylococcus aureus ATCC25923, Esche-richia coli ATCC25922, Enterobacter cloacae ATCC13047, Klebsiella oxytoca ATCC8724, Proteus mirabilis ATCC7002, Proteus vulgaris ATCC6380). The results obtained from antibacterial assay indicated that the synthe- sized Schiff bases 1-10 inhibited potential growth of Klebsiella aerogenes with the minimum inhibitory concentration (MIC) ranging from 15.6 to 31.25 μg·mL^-1 and Enterococcus faecalis with MIC the range between 31.25 and 125 μg· mL^-1 in comparison with the standard nalidixic acid and streptomycin sulfate.
- antibacterial,
- Schiff bases,
- nalidixic,
- synthesis,
- inhibition
1. [1]
  Kealy T, Pauson P. A New Type of Organo-iron Compound[J]. Nature, 1951,168:1039-1040.
2. [2]
  Miller S A, Tebboth J A, Tremaine J F. Dicyclopentadienyliron[J]. J. Chem. Soc., 1952:632-635. doi: 10.1039/jr9520000632
3. [3]
  Wilkinson G, Rosenblum M, Whiting M, Woodward R B. The Structure of Iron Bis-cyclopentadienyl[J]. J. Am. Chem. Soc., 1952,74:2125-2126. doi: 10.1021/ja01128a527
4. [4]
  Dunitz J, Orgel L. Bis-cyclo Pentadienyl Iron: A Molecular Sandwich[J]. Nature, 1953,168:121-122.
5. [5]
  Eric M N, Bernard O, Vincent O. Synthesis, Physical and Antimicrobial Studies of Ferrocenyl-N-(pyridinylmethylene)anilines and Ferrocenyl-N-(pyridinylmethyl)anilines[J]. S. Afr. J. Chem., 2016,69:51-66.
6. [6]
  Werner H. At Least 60 Years of Ferrocene: The Discovery and Rediscovery of the Sandwich Complexes[J]. Angew. Chem. Int. Ed., 2012,51:6052-6058. doi: 10.1002/anie.201201598
7. [7]
  Van Staveren D R, Metzler-Nolte N. Bioorganometallic Chemistry of Ferrocene[J]. Chem. Rev., 2004,104:5931-5985. doi: 10.1021/cr0101510
8. [8]
  Eiland P F, Pepinsky R. X-ray Examination of Iron Biscyclopentadienyl[J]. J. Am. Chem. Soc., 1952,744971.
9. [9]
  Togni A. Ferrocene-Cotaining Charge-Transfer Complexes. Conducting and Magnetic Materials//Togni A, Hayashi T[J]. Ferrocenes: Homogeneous Catalysis, Organic Synthesis, Materials Science. New York: John Wiley & Sons, 2008:433-469.
10. [10]
  Yang H, Chen X, Jiang W, Lu Y. Convenient Synthesis of New Water-Soluble Monosubstituted Functional Ferrocene Derivatives[J]. Inorg. Chem. Commun., 2005,8:853-857. doi: 10.1016/j.inoche.2005.05.025
11. [11]
  Verma S K, Singh V K. Synthesis and Characterization of ferrocene Functionalized Transition Metal Dithiocarbamate Complexes: Investigations of Antimicrobial, Electrochemical Properties and a New Polymorphic Form of[Cu{κ²S, S-S₂CN(CH₂C ₄H₃O)CH₂Fc}₂][J]. J. Org. Chem., 2015,719:214-224.
12. [12]
  Jaouen G, Top S, Vessieres A, Leclercq G, McGlinchey M J. The First Organometallic Selective Estrogen Receptor Modulators (SERMs) and Their Relevance to Breast Cancer[J]. Curr. Med. Chem., 2004,11:2505-2517. doi: 10.2174/0929867043364487
13. [13]
  Ornelas C. Application of Ferrocene and Its Derivatives in Cancer Research[J]. New J. Chem., 2011,35:1973-1985. doi: 10.1039/c1nj20172g
14. [14]
  Hegazy W H. Synthesis of Organometallic-Based Biologically Active Compounds: In Vitro Antibacterial and Antifungal of Asymmetric Ferrocene-Derived Schiff-Bases Chelates[J]. Int. Res. J. Pure Appl. Chem., 2012,2(3):170-182. doi: 10.9734/IRJPAC/2012/1627
15. [15]
  Mziyanda M, Dingle L M K, Devon C, Jo-Anne D M, Dustin L, Dale T, Heinrich C H, Adrienne L E, Setshaba D K. Repurposing a Polymer Precursor: Synthesis and In Vitro Medicinal Potential of Ferrocenyl 1, 3-Benzoxazine Derivatives[J]. Eur. J. Med. Chem., 2020,187111924. doi: 10.1016/j.ejmech.2019.111924
16. [16]
  Calhorda M J, Costa P J, Martinho P N, Gimeno M C, Aguna A, Quintal S, Villacampa M D. Synthesis and Ligand Properties towards Gold and Silver of the Ferrocenylamidobenzimidazole Ligand[J]. J. Org. Chem., 2006,691:4181-4188. doi: 10.1016/j.jorganchem.2006.06.025
17. [17]
  Quintal S, Gimeno M C, Laguna A, Calhorda M J. Silver and Copper Complexes with Ferrocenyl Ligands Bearing Imidazole or Pyridyl Substituents[J]. J. Org. Chem., 2010,695:558-566. doi: 10.1016/j.jorganchem.2009.11.013
18. [18]
  Rajput J, Moss J R, Hutton A T, Hendricks D T, Catherine E A Christopher I. Synthesis, Characterization and Cytotoxicity of Some Palladium, Platinum, Rhodium and Iridium Complexes of Ferrocenylpyridine and Related Ligands: Crystal and Molecular Structure of trans-Dichlorobis(3-ferrocenylpyridine)palladium[J]. J. Org. Chem., 2004,689:1553-1568. doi: 10.1016/j.jorganchem.2004.01.034
19. [19]
  Neuse E W. Macromolecular Ferrocene Compounds as Cancer Drug Models[J]. J. Inorg. Org. Polym. Mater., 2005,15:3-31. doi: 10.1007/s10904-004-2371-9
20. [20]
  Mohammad F R F, Mokhles M A, Rafeek A A, Ammar A L. On the Medicinal Chemistry of Ferrocene[J]. Appl. Org. Chem., 2007,21:613-625. doi: 10.1002/aoc.1202
21. [21]
  Biot C, François N, Maciejewski L, Brocard J, Poulain D. Synthesis and Antifungal Activity of a Ferrocene-Fluconazole Analogue[J]. Bioorg. Med. Chem. Lett., 2000,10:839-841. doi: 10.1016/S0960-894X(00)00120-7
22. [22]
  Seshadri T. Novel Ferrocene-Based Chiral Schiff Base Derivative with a Twist-Grain Boundary Phase (TGBA) and a Blue Phase[J]. Chem. Commun., 1998:735-736.
23. [23]
  Driver M S, Hartwig J F. A Second-Generation Catalyst for Aryl Halide Amination: Mixed Secondary Amines from Aryl Halides and Primary Amines Catalyzed by (DPPF)PdCl₂[J]. J. Am. Chem. Soc., 1996,118:7217-7218. doi: 10.1021/ja960937t
24. [24]
  Bruno S M, Gomes A C, Coelho A C, Brandao P, Valente A A, Pillinger M, Concalves I S. Catalytic Isomerisation of α-Pinene Oxide in the Presence of ETS-10 supported Ferrocenium Ions[J]. J. Org. Chem., 2015,791:66-71. doi: 10.1016/j.jorganchem.2015.05.026
25. [25]
  Siangwata S, Baartzes N, Makhubela B C, Smith J S. Synthesis, Characterisation and Reactivity of Water-Soluble Ferrocenylimine-Rh Complexes as Aqueous-Biphasic Hydroformylation Catalyst Precursors[J]. J. Org. Chem., 2015,796:26-32. doi: 10.1016/j.jorganchem.2015.04.029
26. [26]
  Sakanishi S, Bardwell D A, Couchman S, Jeffery J C, McCleverty J A, Michael D W. Donor/Acceptor Complexes Containing Ferrocenyl-Pyridine Ligands Attached to a Tungsten Carbonyl Centre: Structural, Spectroscopic and Electrochemical Properties[J]. J. Org. Chem., 1997,528:35-45. doi: 10.1016/S0022-328X(96)06395-4
27. [27]
  Casas-Solvas J M, Ortiz-Salmerón E, Fernández I, Garcia-Fuentes L, Santoyo-Gonzlez F, Vargas-Berenguel A. Ferrocene-β-Cyclodextrin Conjugates: Synthesis, Supramolecular Behavior, and Use as Electrochemical Sensors[J]. Chem. Eur. J., 2009,15:8146-8162. doi: 10.1002/chem.200900593
28. [28]
  Rajput J, Hutton A T, Moss J R, Su H, Imrie C. Ferrocenyl-Nitrogen Donor Ligands. Synthesis and Characterization of Rhodium Complexes of Ferrocenylpyridine and Related Ligands[J]. J. Org. Chem., 2006,691:4573-4588. doi: 10.1016/j.jorganchem.2006.05.048
29. [29]
  Park S, Mathur V K, Planap R P. Syntheses, Solubilities and Oxygen Absorption Properties of New Cobalt Schiff-Base Complexes[J]. Polyhedron, 1998,17:325-330. doi: 10.1016/S0277-5387(97)00308-2
30. [30]
  Imrie C, Engelbrecht P, Loubser C, McCleland C W, Nyamori V O, Bogardi R, Levendis D C, Tolom N, Rooyen J V, Williams N. Synthesis of ferrocenylphenyl Derivatives Including Biphenylferrocenes, Arylferrocenylphenyl Ethers and Arylferrocenylphenyl Amines[J]. J. Org. Chem., 2002,645:65-81. doi: 10.1016/S0022-328X(01)01410-3
31. [31]
  Landy L F. The Chemistry of Macrocyclic Ligand Complexes. Cambridge: Cambridge University Press, 1989.
32. [32]
  Choi Y K, Kim W S, Chung K I, Chung M W, Nam H P. Catalytic Effect of Transition Metal-N, N'-Bis(naphthaldehyde)diimines on Reduction of Thionyl Chloride[J]. Microchem. J., 2000,65:3-15. doi: 10.1016/S0026-265X(00)00011-4
33. [33]
  Chohan Z H, Praveen M. Synthesis, Characterization, Coordination and Antibacterial Properties of Novel Asymmetric 1, 1'-Disubstituted Ferrocene-Derived Schiff-Base Ligands and Their Co, Cu, Ni and Zn Complexes[J]. Appl. Org. Chem., 2001,15:617-625. doi: 10.1002/aoc.179
34. [34]
  Gupta K, Sutar A K. Catalytic Activities of Schiff Base Transition Metal Complexes[J]. Coord. Chem. Rev., 2008,252:1420-1450. doi: 10.1016/j.ccr.2007.09.005
35. [35]
  Asghari G, Zareen A, Muhammad S, Sehrish S, Bushra M. Ferrocene-Based Aliphatic and Aromatic Poly(azomethine) Esters: Synthesis, Physicochemical Studies, and Biological Evaluation[J]. Macromolecules, 2013,46:2800-2807. doi: 10.1021/ma400192u
36. [36]
  Rajavel R, Vadivu M S, Anitha C. Synthesis, Physical Characterization and Biological Activity of Some Schiff Base Complexes[J]. Eur. J. Chem., 2008,5:620-626.
37. [37]
  Muhammad S, Zareen A, Iqbal A, Safeer A, Michael B, Hammad I, Bushra M. Ferrocene-Based Schiff Bases Copper Complexes: Synthesis, Characterization, Biological and Electrochemical Analysis[J]. Inorg. Chim. Acta, 2017,463:102-111. doi: 10.1016/j.ica.2017.04.034
38. [38]
  Thomson A J, Gray H B. Bio-inorganic Chemistry[J]. Curr. Opin. Chem. Biol., 1998,2(2):155-158. doi: 10.1016/S1367-5931(98)80056-2
39. [39]
  Saravanan V, Kannan A, Rajakumar P. Synthesis, Characterization, Optical and Electrochemical Properties and Antifungal and Anticancer Activities of Ferrocenyl Conjugated Novel Dendrimers[J]. New J. Chem., 2017,41:1714-1722. doi: 10.1039/C6NJ01120A
40. [40]
  Hodnett M, Mooney P D. Structure-Antitumor Activity Correlation of Some Schiff Bases[J]. J. Med. Chem., 1970,13:768-770. doi: 10.1021/jm00298a054
41. [41]
  Veronika K, Aleksandar V, Vladimir R, Kojić-Prodić B. Ferrocene Compounds. XL. Synthesis and Characterization of Ferrocene Schiff Bases[J]. J. Mol. Struct., 2004,687:107-110. doi: 10.1016/j.molstruc.2003.09.014
42. [42]
  Ikhile M I, Ngila J C. Synthesis and Characterization of Some Ferrocenylphenylimine Compound[J]. Chinese J. Inorg. Chem., 2015,31(10):2079-2088.
43. [43]
  Andrews J M. Determination of Minimum Inhibitory Concentrations[J]. J. Antimicrob. Chemother., 2001,48:5-16. doi: 10.1093/jac/48.suppl_1.5
44. [44]
  Dalhoff A. In Vitro Activities of Quinolones. Expert Opin[J]. Investig. Drugs, 1999,8:123-137.
45. [45]
  Muhammad Z, Afzal S, Zareen A, Rumana Q, Bushra M, Misbah T, Michael B. Synthesis, Characterization, Electrochemistry and Evaluation of Biological Activities of Some Ferrocenyl Schiff Bases[J]. Appl. Org. Chem., 2011,25:61-69. doi: 10.1002/aoc.1690
46. [46]
  Liu Y T, Yang L S, Yin D W, Dang Y, Yang L, Zou Q, Li J, Sun J X. Solvent-Free Synthesis, Characterization, Biological Activity of Schiff Bases and their Metal Complexes Derived from Ferrocenyl Chalcone[J]. J. Org. Chem., 2019,899120903. doi: 10.1016/j.jorganchem.2019.120903
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