Skip to main content
SpringerLink
Log in

Synthesis, Antioxidant and Antibacterial Effects of Chalcone-Triazine Hybrid Metal Complexes

  • Original Article
  • Published:
Chemistry Africa Aims and scope Submit manuscript

Abstract

In our earlier attempt, we have successfully synthesized and evaluated the antioxidant ability of the metal complexes of the chalcone-triazine hybrid with phenoxy [-6-phenoxy-] group at C6. Herein, we hypothesized that the substitution of phenyl amino [-6-(phenyl)amino-] group would enhance the biological effects of the metal complexes of chalconce-triazine hybrids. It is observed that the antioxidant ability of the metal (Cu2+, Co2+, Zn2+, Fe2+) complexes of chalcone-triazine hybrids with -6-phenoxy- or -6-(phenyl)amino- substitutions at are almost same (< 35 μg/mL). Whereas, the novel chalconce-triazine hybrids with -6-(phenyl)amino- exhibited antibacterial effect on E. coli and S. aureus (> 10 mm zone of inhibition) which was absent in the earlier one. In specific, the Cu-complex of (1-(2,4-dihydroxyphenyl)-3-(4-((4-((4-nitrophenyl)amino)-6-(phenyl)amino)-1,3,5-triazin-2-yl)oxy)phenyl)prop-2-en-1-one exhibited the highest antibacterial effect as 24.8 and 22.6 mm zone of inhibition on E. coli and S. aureus, respectively. Synthesized flavonoid metal complexes were characterized by Elemental Analysis, NMR, FT-IR, UV–Visible spectroscopy and XRD analytical techniques.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1
Scheme 2
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6

Similar content being viewed by others

References

  1. Rezk BM, Haenen GRMM, Fvan der Vijgh WJ, Bast A (2002) The antioxidant activity of phloretin: the disclosure of a new antioxidant pharmacophore in flavonoids. Biochem Biophys Res Commun 295:9–13

    Article  CAS  PubMed  Google Scholar 

  2. Bozic DD, Milenkovic M, Ivkovic B, Cirkovic I (2014) Antibacterial activity of three newly-synthesized chalcones & synergism with antibiotics against clinical isolates of methicillin-resistant Staphylococcus aureus. Indian J Med Res 140(1):130–137

    CAS  PubMed  PubMed Central  Google Scholar 

  3. Saumya S, Milan KM, Anup M, Ashmita S, Surajit KG, Hans RB, Udaya PS (2021) 1,3,5-Triazine: a versatile pharmacophore with diverse biological activities. Arch Pharm. https://doi.org/10.1002/ardp.202000363

    Article  Google Scholar 

  4. Havrankova E, Calkovska N, Padrtova T, Csollei J, Opatrilova R, Pazdera P (2020) Antioxidative activity of 1,3,5-triazine analogues incorporating aminobenzene sulfonamide, aminoalcohol/phenol, piperazine, chalcone, or stilbene motifs. Molecules 25:1787. https://doi.org/10.3390/molecules25081787

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  5. Anjani S, Kishor K, Ana S, Marina D, Irini GA (2010) Synthesis of some new S-triazine based chalcones and their derivatives as potent antimicrobial agents. Eur J Med Chem 45:510–518

    Article  Google Scholar 

  6. Patle SK, Kawathekar N, Zaveri M, Kamaria P (2013) Synthesis and evaluation of 2,4,6-trisubstituted pyrimidine derivatives as novel antileishmanial agents. Med Chem Res 22:1756–1761

    Article  CAS  Google Scholar 

  7. El-Wakil MH, Khattab SN, El-Yazbi AF, El-Nikhely N, Soffar A, Khalil HH (2020) New chalcone-tethered 1,3,5-triazines potentiate the anticancer effect of cisplatin against human lung adenocarcinoma A549 cells by enhancing DNA damage and cell apoptosis. Bioorg Chem. https://doi.org/10.1016/j.bioorg.2020.104393

    Article  PubMed  Google Scholar 

  8. Wang Y, Tang X, Yi L (2019) Design and discovery of novel 1,3,5-triazines as dipeptidyl peptidase-4 inhibitor against diabetes. Pharmacology 103(5–6):273–281

    Article  CAS  PubMed  Google Scholar 

  9. Sulpizio C, Muller ST, Zhang Q, Brecker L, Rompel A (2016) Synthesis, characterization, and antioxidant activity of Zn2+ and Cu2+ coordinated polyhydroxychalcone complexes. Monatsh Chem 147:1871–1881

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  10. El SayedAly MR, Abd El RazekFodah HH, Saleh SY (2014) Antiobesity, antioxidant and cytotoxicity activities of newly synthesized chalcone derivatives and their metal complexes. Eur J Med Chem 76:517–530

    Article  Google Scholar 

  11. Atlam FM, El-Nahass MN, Bakr EA, Fayed TA (2017) Metal complexes of chalcone analogue: Synthesis, characterization, DNA binding, molecular docking and antimicrobial evaluation. Appl Organometal Chem 32:e3951

    Article  Google Scholar 

  12. El-Sayed YS, Gaber M (2015) Studies on chalcone derivatives: complex formation, thermal behavior, stability constant and antioxidant activity. Spectrochim Acta Part A: Mol Biomol Spectrosc 137:423–431

    Article  CAS  Google Scholar 

  13. Rice-Evans CA, Packer L (eds) (2003) Flavonoids in health and disease. CRC Press, Boca Raton

    Google Scholar 

  14. Karthikeyan A, Suresh J, Balaji K, Anandhakumar S, Arun A (2022) Synthesis, characterization and antioxidant property of nano-scaled metal complexes of triazine based hydroxy chalcone. Smart Sci. https://doi.org/10.1080/23080477.2022.2074660

    Article  Google Scholar 

  15. Suresh J, Vakees E, Uma P, Revathy S, Karthikeyan A, Arun A (2016) UV cross-linkable polymer based on triazine: synthesis, characterization and crosslinking studies. Macromol Symp 362:11–17

    Article  CAS  Google Scholar 

  16. Thangaraj V, Chang J-H, Dash CS, Sundararajan M, Mohanraj K, Ahmad N, Alshehri AM, Mathankumar K, Sumathi S, Yuvaraj S, Arun A (2022) Study of structural, optical, antibacterial, anticancer effects on MDA-MB-231 cell line and drug delivery characteristics of novel Ce4-xCs2 (1+x)Fe5-xZnxO14+δ [0≤x≤0.45] nanocomposite prepared via sol-gel synthesis technique. Surf Interfaces 29:101746

    Article  CAS  Google Scholar 

  17. Omar MM, Mohamed GG, Ibrahim AA (2009) Spectroscopic characterization of metal complexes of novel Schiff base. Synthesis, thermal and biological activity studies. Spectrochim Acta 73:358–369

    Article  CAS  Google Scholar 

  18. Sumathi S, Anitha C, Tharmaraj P, Sheela CD (2011) Spectral, NLO, fluorescence, and biological activity of knoevenagel condensate of β-diketone ligands and their metal(II) complexes. Int J Inorganic. Chem 154326

  19. Singh G, Kalra P, Arora A, Singh G, Sharma S, Satija P (2018) Chalcone scaffolds as photofunctional hybrid material of indolin-2-one-functionalized siloxy framework for optical sensing of Cu2+. N J Chem 42:16902

    Article  CAS  Google Scholar 

  20. Karamunge KG, Vibhute YB (2012) Synthesis and structural studies of complexes of cu (ii), ni (ii) and co (ii) with 2’-hydroxy chalconesint. J Chem Sci 10:490–500

    CAS  Google Scholar 

  21. Sulpizio C, Breibeck J, Rompel A (2018) Recent progress in synthesis and characterization of metal chalcone complexes and their potential as bioactive agents. Coord Chem Rev 374:497–524

    Article  CAS  Google Scholar 

  22. Basubaul TS, Addepalli MR, Duthie A, Priyasingh B, Koch H, Gildenast U, Englert IR, Leon HH (2020) Triorganotin(IV) derivatives with semirigid heteroditopic hydroxo-carboxylato ligands:Synthesis, characterization, and cytotoxic properties. Appl Organometal Chem 35:e6080

    Google Scholar 

  23. Borge VV, Patil RM (2019) Syntheses and characterization of copper metal complexes prepared from chalcone derivatives. Microchemi J 145:456–459

    Article  CAS  Google Scholar 

  24. Azaroff LV (1968) Elements of X-ray crystallography hardcover. Elements of X-ray Crystallography

  25. Burger MJ (1960) Crystal structure analysis. Wiley, Hoboken

    Google Scholar 

  26. Muthukumar M, Viswanathamurthi P (2010) Studies on ruthenium(III) chalconate complexes containing PPh3/AsPh3.phosphorus sulfur silicon. Relat Elem 185:2201–2211

    Article  CAS  Google Scholar 

  27. Kafi-Ahmadi L, Shirmohammadzadeh L (2017) Synthesis of Co(II) and Cr(III) salicylidenic Schiff base complexes derived from thiourea as precursors for nano-sized Co3O4 and Cr2O3 and their catalytic, antibacterial properties. J Nanostructure Chem 7:179–190

    Article  CAS  Google Scholar 

  28. Narendrakumar C, Parashram M (2017) Metal complexes of a novel schiff base based on penicillin: characterization, molecular modeling, and antibacterial activity study. Bioinorg Chem Appl 13:6927675

    Google Scholar 

  29. Abdel-Mottalab MSA, Ismail EH (2019) Transition metal complexes of mixed bioligands:synthesis, characterization, DFT modeling, and applications. J Chem 18:3241061

    Google Scholar 

  30. Dhanaraj CJ, Nair MS (2009) Synthesis, characterization, and antimicrobial studies of some Schiffbase metal(II) complexes. J Coord Chem 62:4018–4028

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Thiruvalluvar University, Vellore, Tamilnadu, 632 115, India

    A. Karthikeyan & S. Manikandan

  2. Department of Chemistry, Kalaignar Karunanidhi Government Arts College, Tiruvannamalai, Tamilnadu, 606 603, India

    A. Karthikeyan, J. Suresh, K. Balaji, S. Manikandan, C. Sudhakar & A. Arun

  3. Department of Chemistry, SCSVMV University, Enathur, Kanchipuram, Tamilnadu, 631 561, India

    K. Sivakumar

Authors
  1. A. Karthikeyan
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. J. Suresh
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. K. Balaji
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. S. Manikandan
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. C. Sudhakar
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. K. Sivakumar
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. A. Arun
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to A. Arun.

Ethics declarations

Conflict of interest

On behalf of all authors, the corresponding author states that there is no conflict of interest.

Rights and permissions

Springer Nature or its licensor holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Karthikeyan, A., Suresh, J., Balaji, K. et al. Synthesis, Antioxidant and Antibacterial Effects of Chalcone-Triazine Hybrid Metal Complexes. Chemistry Africa 6, 275–286 (2023). https://doi.org/10.1007/s42250-022-00496-0

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s42250-022-00496-0

Keywords

Search

Navigation