Research Article

p-Cymene Based Organometallic Ruthenium(II)-Arene Complexes with Benzaldehyde Derived Thiosemicarbazones: Synthesis, Characterization and Antimicrobial Activity

Volume: 44 Number: 4 December 5, 2017
  • Murat Yavuz *
  • Pelin Köse Yaman
  • Nurdan Öztürk
  • Suna Timur
  • Elif Subaşı

p-Cymene Based Organometallic Ruthenium(II)-Arene Complexes with Benzaldehyde Derived Thiosemicarbazones: Synthesis, Characterization and Antimicrobial Activity

Abstract

Objective: Thiosemicarbazone (TSC) containing three new mononuclear ruthenium(II)-arene complexes were synthesized so as to contribute to the development of ruthenium complexes with pharmacologically attracted properties.
Methods: Reactions of the ruthenium(II)-arene dimer [{RuCl(μ-Cl)(η6-p-cymene)}2] (1) with the respective TSC1-3 (1:2 molar ratio) in methanol resulted in p-cymene containing new conformationally rigid half-sandwich organometallic ruthenium(II)-arene complexes; [(η6-p-cymene)Ru(TSC1-κ3O,N,S)]Cl (I), [(η6-p-cymene)Ru(Cl)(TSC2-κ2N,S)]Cl (II), and [(η6-p-cymene)Ru(Cl)(TSC3-κ2N,S)]Cl (III). The molecular structures of complexes I, II and III were elucidated on the spectroscopic data obtained by the application of 1H NMR, Fourier transform infrared (FT-IR), UV-vis and elemental analysis techniques. In vitro antimicrobial activities of the synthesized three ruthenium(II)-arene complexes were evaluated using the disc diffusion method.
Results: The spectroscopic data indicated that TSC1 was bounded to the metal as a tridentate ligand with its thione sulfur atom, phenolic oxygen atom and azomethine nitrogen atom in the complex I, while TSC2 and TSC3 were bounded to metal center as bidentate manner through their thione sulfur atom and imine nitrogen (C=N) atom in the complexes II and III, respectively. The obtained antimicrobial activity results showed that these complexes efficiently inhibit the growth of Gram-positive bacterial strains.
Conclusion: The TSC1-3 containing ruthenium(II)-arene complexes were successfully synthesized and their molecular structures were also determined by the spectroscopic methods. All ruthenium(II)-arene complexes showed higher antibacterial activities against Gram-positive bacterial strains than the Gram-negative ones.
Keywords:

Keywords

References

  1. 1. Klayman DL, Scovill JP, Bartosevich JF, Bruce J. 2-Acetylpyridine thiosemicarbazones. 5. 1-[1-(2-Pyridyl)ethyl]-3-thiosemicarbazides as potential antimalarial agents. J Med Chem. 1983;26:35–9. https://doi.org/10.1021/jm00355a008
  2. 2. Atalay T, Akgemci EG. Thermodynamic studies of some complexes of 2-benzoylpyridine 4-phenyl-3-thiosemicarbazone. Turk J Chem. 1998;22:123–7.
  3. 3. Beraldo H, Gambino D. The wide pharmacological versatility of semicarbazones, thiosemicarbozones and their metal complexes. Mini-Rev Med Chem. 2004; 4: 31–9. https://doi.org/10.2174/1389557043487484
  4. 4. Garcia-Tojal J, Garcia-Orad A, Serra JL, et al. Synthesis and spectroscopic properties of copper(II) complexes derived from thiophene-2-carbaldehyde thiosemicarbazone. Structure and biological activity of [Cu(C6H6N3S2)2]. J Inorg Biochem. 1999;75:45–54. https://doi.org/10.1016/S0162-0134(99)00031-8
  5. 5. Haraguchi SK, Silva AA, Vidotti GJ, et al. Antitrypanosomal activity of novel benzaldehyde-thiosemicarbazone derivatives from kaurenoic acid. Molecules. 2011; 16: 1166 – 80. https://doi.org/ 10.3390/molecules16021166
  6. 6. Dimmock JR, McColl JM, Wonkol SL, Thayer RS, Hancock DS. Evaluation of the thiosemicarbazones of some aryl alkyl ketones and related compounds for anticonvulsant activities. Eur J Med Chem. 1991;26: 529–34. https://doi.org/10.1016/0223-5234(91)90148-G
  7. 7. Sharma S, Athar F, Maurya MR, Azam, A. Copper(II) complexes with substituted thiosemicarbazones of thiophene-2-carboxaldehyde: Synthesis, characterization and antiamoebic activity against E. histolytica. Eur J Med Chem. 2005;40:1414–19. https://doi.org/ 10.1016/j.ejmech.2005.05.013
  8. 8. Singh S, Bharti N, Mohapatra PP. Chemistry and biology of synthetic and naturally occurring antiamoebic agents. Chem Rev. 2009;109:1900–47. https://doi.org/10.1021/cr068217k

Details

Primary Language

English

Subjects

Health Care Administration

Journal Section

Research Article

Publication Date

December 5, 2017

Submission Date

December 5, 2017

Acceptance Date

-

Published in Issue

Year 2017 Volume: 44 Number: 4

APA
Yavuz, M., Yaman, P. K., Öztürk, N., Timur, S., & Subaşı, E. (2017). p-Cymene Based Organometallic Ruthenium(II)-Arene Complexes with Benzaldehyde Derived Thiosemicarbazones: Synthesis, Characterization and Antimicrobial Activity. Dicle Medical Journal, 44(4), 381-394. https://doi.org/10.5798/dicletip.362482
AMA
1.Yavuz M, Yaman PK, Öztürk N, Timur S, Subaşı E. p-Cymene Based Organometallic Ruthenium(II)-Arene Complexes with Benzaldehyde Derived Thiosemicarbazones: Synthesis, Characterization and Antimicrobial Activity. Dicle Medical Journal. 2017;44(4):381-394. doi:10.5798/dicletip.362482
Chicago
Yavuz, Murat, Pelin Köse Yaman, Nurdan Öztürk, Suna Timur, and Elif Subaşı. 2017. “P-Cymene Based Organometallic Ruthenium(II)-Arene Complexes With Benzaldehyde Derived Thiosemicarbazones: Synthesis, Characterization and Antimicrobial Activity”. Dicle Medical Journal 44 (4): 381-94. https://doi.org/10.5798/dicletip.362482.
EndNote
Yavuz M, Yaman PK, Öztürk N, Timur S, Subaşı E (December 1, 2017) p-Cymene Based Organometallic Ruthenium(II)-Arene Complexes with Benzaldehyde Derived Thiosemicarbazones: Synthesis, Characterization and Antimicrobial Activity. Dicle Medical Journal 44 4 381–394.
IEEE
[1]M. Yavuz, P. K. Yaman, N. Öztürk, S. Timur, and E. Subaşı, “p-Cymene Based Organometallic Ruthenium(II)-Arene Complexes with Benzaldehyde Derived Thiosemicarbazones: Synthesis, Characterization and Antimicrobial Activity”, Dicle Medical Journal, vol. 44, no. 4, pp. 381–394, Dec. 2017, doi: 10.5798/dicletip.362482.
ISNAD
Yavuz, Murat - Yaman, Pelin Köse - Öztürk, Nurdan - Timur, Suna - Subaşı, Elif. “P-Cymene Based Organometallic Ruthenium(II)-Arene Complexes With Benzaldehyde Derived Thiosemicarbazones: Synthesis, Characterization and Antimicrobial Activity”. Dicle Medical Journal 44/4 (December 1, 2017): 381-394. https://doi.org/10.5798/dicletip.362482.
JAMA
1.Yavuz M, Yaman PK, Öztürk N, Timur S, Subaşı E. p-Cymene Based Organometallic Ruthenium(II)-Arene Complexes with Benzaldehyde Derived Thiosemicarbazones: Synthesis, Characterization and Antimicrobial Activity. Dicle Medical Journal. 2017;44:381–394.
MLA
Yavuz, Murat, et al. “P-Cymene Based Organometallic Ruthenium(II)-Arene Complexes With Benzaldehyde Derived Thiosemicarbazones: Synthesis, Characterization and Antimicrobial Activity”. Dicle Medical Journal, vol. 44, no. 4, Dec. 2017, pp. 381-94, doi:10.5798/dicletip.362482.
Vancouver
1.Murat Yavuz, Pelin Köse Yaman, Nurdan Öztürk, Suna Timur, Elif Subaşı. p-Cymene Based Organometallic Ruthenium(II)-Arene Complexes with Benzaldehyde Derived Thiosemicarbazones: Synthesis, Characterization and Antimicrobial Activity. Dicle Medical Journal. 2017 Dec. 1;44(4):381-94. doi:10.5798/dicletip.362482

Cited By