Generic placeholder image

Medicinal Chemistry


ISSN (Print): 1573-4064
ISSN (Online): 1875-6638

Research Article

Synthesis and Evaluation of 5-imino-4-thioxoimidazolidin-2-one Derivatives as Antibacterial and Antifungal Agents

Author(s): Samir Y. Abbas*, Marwa A.M. Sh. El-Sharief, Reem A.K. Al-Harbi, Eman W. El-Gammal and Ahmed M.S. El-Sharief

Volume 17, Issue 6, 2021

Published on: 27 December, 2019

Page: [638 - 645] Pages: 8

DOI: 10.2174/1573406416666191227112648

Price: $65


Objective: It was interesting to synthesize some new 5-imino-4-thioxoimidazolidin-2- one derivatives with different halogenated and alkylated aromatic substituents at N-(1) and N-(3) and evaluation of their expected antibacterial and antifungal activities.

Methods: New 5-imino-4-thioxoimidazolidin-2-one derivatives were synthesized through the reaction of different halogenated and alkylated N-arylcyanothioformamides with halogenated and alkylated aryl isocyanates.

Results: 5-Imino-4-thioxoimidazolidin-2-ones were obtained in high yields with excellent purity. The activities of imidazolidines as antibacterial and antifungal agents were studied. Some of the imidazolidine derivatives displayed significant antibacterial and antifungal activities.

Conclusion: 5-Imino-4-thioxoimidazolidin-2-ones were obtained in 77-90% yields with excellent purity. The antibacterial and antifungal activities suggest that some of the imidazole derivatives possess significant antimicrobial activity against B. subtilis, K. pneumonia and C. albicans and moderate activity against S. aureus.

Keywords: N-Arylcyanothioformamides, 5-imino-4-thioxoimidazolidin-2-ones, imidazolidineiminothiones, antibacterial activity, antifungal activity, antimicrobial activity.

Graphical Abstract
Alberts, B.; Bray, D.; Lewis, J.; Raff, M.; Roberts, K.; Watson, J.D. Molecular Biology of the Cell, 3rd ed; Garland: New York, 1994, p. 736.
Gao, Z.; Duhl, D.D.; Harrison, S.D. Beyond kinases: Purine-binding enzymes as cancer targets. Annu. Rep. Med. Chem., 2003, 38, 193-202.
Trunz, B.B.; Jędrysiak, R.; Tweats, D.; Brun, R.; Kaiser, M.; Suwiński, J.; Torreele, E. 1-Aryl-4-nitro-1H-imidazoles, a new promising series for the treatment of human African trypanosomiasis. Eur. J. Med. Chem., 2011, 46(5), 1524-1535.
[] [PMID: 21353728]
Chazeau, V.; Cussac, M.; Boucherle, A. Synthesis and immunomodulating activity of 1-amino-2-thiohydantoin derivatives. Eur. J. Med. Chem., 1992, 27, 839-843.
Bascou, J.P.; Lacroix, G.; Gadras, A.; Perez, J. Derives optiquement actifs de 2-imidazoline-5-one et 2-imidazoline-5-thiones fungicide. 1994. E P Patent 1994, 0 629616 A2.
Rogawski, M.A.; Löscher, W. The neurobiology of antiepileptic drugs. Nat. Rev. Neurosci., 2004, 5(7), 553-564.
[] [PMID: 15208697]
Kassouf, W.; Tanguay, S.; Aprikian, A.G. Nilutamide as second line hormone therapy for prostate cancer after androgen ablation fails. J. Urol., 2003, 169(5), 1742-1744.
[] [PMID: 12686822]
Odake, S.; Morikawa, T.; Tsuchiya, M.; Imamura, L.; Kobashi, K. Inhibition of Helicobacter pylori urease activity by hydroxamic acid derivatives. Biol. Pharm. Bull., 1994, 17(10), 1329-1332.
[] [PMID: 7874052]
Turbanti, L.; Cerbai, G.; Di Bugno, C.; Giorgi, R.; Garzelli, G.; Criscuoli, M.; Renzetti, A.R.; Subissi, A.; Bramanti, G.; DePriest, S.A. 1,2-Cyclomethylenecarboxylic monoamide hydroxamic derivatives. A novel class of non-amino acid angiotensin converting enzyme inhibitors. J. Med. Chem., 1993, 36(6), 699-707.
[] [PMID: 8459398]
Ammar, Y.A.; El-Sharief, M.A.M.Sh.; Ghorab, M.M.; Mohamed, Y.A.; Ragab, A.; Abbas, S.Y. New imidazolidineiminothione, imidazolidin-2-one, and imidazoquinoxaline derivatives: synthesis and evaluation of antibacterial and antifungal activities. Curr. Org. Synth., 2016, 13(3), 466-475.
[] [PMID: 27594815]
Moussa, Z.; El-Sharief, M.A.M.S.; Abbas, S.Y. New imidazolidineiminothione derivatives: Synthesis, spectral characterization and evaluation of antitumor, antiviral, antibacterial and antifungal activities. Eur. J. Med. Chem., 2016, 122, 419-428.
[] [PMID: 27393950]
El-Sharief, M.A.M.Sh.; Abbas, S.Y.; Zahran, M.A.; Mohamed, Y.A.; Ragab, A.; Ammar, Y.A. New 1,3-diaryl-5-thioxo-imidazolidin-2,4-dione derivatives: synthesis, reactions and evaluation of antibacterial and antifungal activities. Z. Naturforsch. B, 2016, 71, 875-881.
El-Sharief, M.A.M.S.; Abbas, S.Y.; El-Sharief, A.M.S.; Sabry, N.M.; Moussa, Z.; El-Messery, S.M.; Elsheakh, A.R.; Hassan, G.S.; El Sayed, M.T. 5-Thioxoimidazolidine-2-one derivatives: Synthesis, anti-inflammatory activity, analgesic activity, COX inhibition assay and molecular modelling study. Bioorg. Chem., 2019, 87, 679-687.
[] [PMID: 30953887]
El-Sharief, M.A.M.Sh.; Abbas, S.Y.; Moussa, Z.; El-Gammal, E.W.; El-Sharief, A.M.Sh. Synthesis and evaluation of antibacterial and antifungal activities of 1,3-disubstituted-4-thioxoimidazolidin-2-one derivatives. Croat. Chem. Acta, 2018, 91, 335-340.
Murray, P.R.; Baron, E.J.; Pfaller, M.A.; Tenover, F.C.; Yolki, R.H. Manual of clinical microbiology, 6th ed; American Society for Microbiology Washington: DC, 1995.

Rights & Permissions Print Export Cite as
© 2022 Bentham Science Publishers | Privacy Policy