Skip to main navigation menu Skip to main content Skip to site footer


Vol 9 No 2 (2024): December

Novel Synthesis of Thiopyrimidine Compounds from Dibenzo-18-Crown-6 and Evaluation of Antibacterial Activity

(*) Corresponding Author
October 11, 2023


In this study, we present a novel synthesis approach for the production of thiopyrimidine compounds, including P-OH-Thiopyrimidine, P-NO2-Thiopyrimidine, and P-Cl2-Thiopyrimidine, from the precursor compound dibenzo-18-crown-6 (DB-18-CE-6). These thiopyrimidine compounds have shown significant potential for various applications, particularly as antibacterial agents. The synthesis involved the reaction of DB-18-CE-6-derived alpha-beta unsaturated ketones with thiourea in a basic medium, resulting in successful cyclization. The synthesized thiopyrimidine compounds were evaluated for their antibacterial activity against common bacterial strains, including Streptococcus, Staphylococcus, and Proteus, and compared to the antibiotic Azithromycin. The results demonstrated that the thiopyrimidine compounds (Z, Z1, Z2, Z3) exhibited excellent antibacterial activity, surpassing Azithromycin, and highlighting their potential as effective alternatives to combat bacterial infections. This research opens new avenues for the development of antibacterial agents and emphasizes the significance of thiopyrimidine compounds in addressing bacterial resistance issues.

Highlights : 

  • Novel synthesis of thiopyrimidine compounds from DB-18-CE-6.
  • Evaluation of antibacterial activity against Streptococcus, Staphylococcus, and Proteus.
  • Potential of thiopyrimidine compounds as effective antibacterial agents.

Keywords : Thiopyrimidine compounds, Antibacterial activity, DB-18-CE-6, Novel synthesis, Bacterial resistance.


  1. D. Septianingtyas, N. Zafira, Z. Zulhipri, F. Kurniadewi, H. Dianhar, Eds., "Green synthesis of chalcones derivatives," in AIP Conference Proceedings, 2021.
  2. B. M. Sahoo, M. Rajeswari, P. Jnyanaranjan, S. Binayani, "Green expedient synthesis of pyrimidine derivatives via chalcones and evaluation of their anthelmintic activity," Indian Journal of Pharmaceutical Education and Research, vol. 51, no. 4S, pp. S700-S6, 2017.
  3. R. Izatt, "Synthetic multidentate macrocyclic compounds," Elsevier, 2012.
  4. G. W. Gokel, W. M. Leevy, M. E. Weber, "Crown ethers: sensors for ions and molecular scaffolds for materials and biological models," Chemical reviews, vol. 104, no. 5, pp. 2723-2750, 2004.
  5. M. Febles, S. Montalvão, G. D. Crespín, M. Norte, J. M. Padrón, P. Tammela, et al., "Synthesis and biological evaluation of crown ether acyl derivatives," Bioorganic & Medicinal Chemistry Letters, vol. 26, no. 22, pp. 5591-5593, 2016.
  6. M. K. Marwan, J. A. Layla, "Synthesis, Characterization and Biological studies of new crown ether derivatives," 2009.
  7. W. M. Leevy, G. M. Donato, R. Ferdani, W. E. Goldman, P. H. Schlesinger, G. W. Gokel, "Synthetic Hydraphile Channels of Appropriate Length Kill Escherichia coli," Journal of the American Chemical Society, vol. 124, no. 31, pp. 9022-9023, 2002.
  8. M. Kralj, L. Tušek‐Božić, L. Frkanec, "Biomedical potentials of crown ethers: prospective antitumor agents," ChemMedChem: Chemistry Enabling Drug Discovery, vol. 3, no. 10, pp. 1478-1492, 2008.
  9. H. A. Younis, "Design, Synthesis, Characterization and biological studies of New mono, dipeptide Prodrugs, and their Bioactivity" 2023.
  10. J. P. Rufino, L. G. V. Sousa, A. E. L. Rodrigues, A. L. S. Falcão, I. C. de Melo Lima, L. A. de Miranda Cavalcanti, et al., "Bacterial resistance to azithromycin: causes, effects, and the fight against COVID-19," Research, Society and Development, vol. 11, no. 6, pp. e27711629198-e27711629198, 2022.
  11. H. H. Bahjat, R. A. Ismail, G. M. Sulaiman, M. S. Jabir, "Magnetic field-assisted laser ablation of titanium dioxide nanoparticles in water for anti-bacterial applications," Journal of Inorganic and Organometallic Polymers and Materials, pp. 3649-3656, 2021.
  12. M. A. Jihad, F. T. Noori, M. S. Jabir, S. Albukhaty, F. A. AlMalki, A. A. Alyamani, "Polyethylene glycol functionalized graphene oxide nanoparticles loaded with nigella sativa extract: a smart antibacterial therapeutic drug delivery system," Molecules, vol. 26, no. 11, pp. 3067, 2021.
  13. M. S. Jabir, T. M. Rashid, U. M. Nayef, S. Albukhaty, F. A. AlMalki, J. Albaqami, et al., "Inhibition of Staphylococcus aureus α-hemolysin production using nanocurcumin capped Au@ ZnO nanocomposite," Bioinorganic Chemistry and Applications, vol. 2022, 2022.
  14. J. Rebek Jr, J. Trend, R. Wattley, S. Chakravorti, "Allosteric effects in organic chemistry. Site-specific binding," Journal of the American Chemical Society, vol. 101, no. 15, pp. 4333-4337, 1979.
  15. M. Xu, P. Wu, F. Shen, J. Ji, K. Rakesh, "Chalcone derivatives and their antibacterial activities: Current development," Bioorganic Chemistry, vol. 91, pp. 103133, 2019.
  16. A. T. Feßler, Y. Wang, C. Wu, S. Schwarz, "Mobile macrolide resistance genes in staphylococci," Plasmid, vol. 99, pp. 2-10, 2018.


Download data is not yet available.