Imidazole Phenanthroline Derivatives: A Promising Application in Modern Medicine
Abstract
Purpose: The primary objective of this study is to create a new class of imidazole phenanthroline compounds that target the 1,10-phenanthroline core for its antifungal and antibacterial properties.
Methods: Commercially available 1,10-phenanthroline (phen) was nitrated with potassium bromide in the presence of sulfuric and nitric acids to get 1,10-phenanthroline-5,6-dione (phendione), an intermediate molecule, which served as the starting compound for the synthesis of 1H-imidazo [4,5-f] [1,10] phenanthroline compounds. This intermediate product was dissolved in glacial acetic acid and then reacted with different benzaldehydes while ammonium acetate acted as a catalyst. Thin Layer Chromatography (TLC) was used to track the reaction's progress and the purity of the product. Their biological efficacy against in vitro bacterial and fungal growth was also investigated. The antimicrobial potential of the investigated compounds when compared to the standards Clotrimazole and Streptomycin, respectively, revealed impressive antifungal and antibacterial properties.
Results: A series of compounds were synthesized successfully and characterized by various analytical techniques such as NMR, IR and ESI-mass spectroscopy. The compounds possess remarkable antibacterial and antifungal potential.
Conclusion: A series of imidazole phenanthrolines were synthesized and found to have antimicrobial activities.
Keywords: phenanthrene, imidazole phenanthroline, 1,10-phenanthroline, potassium bromide, 1,10-phenanthroline-5,6-dione, 1H-imidazo [4,5-f] [1,10] phenanthroline
Keywords:
phenanthrene, imidazole phenanthroline, 1,10-phenanthroline, potassium bromide, 1,10-phenanthroline-5,6-dione, 1H-imidazo [4,5-f] [1,10]DOI
https://doi.org/10.22270/jddt.v15i6.7230References
1. Sammes PG, Yahioglu G. 1,10-Phenanthroline: a versatile ligand. Chem. Soc. Rev. 1994; 23(5):327-334. https://doi.org/10.1039/cs9942300327
2. Luman CR, Castellano FN. Phenanthroline Ligands in Comprehensive Coordination Chemistry II. Elsevier 2003. ISBN 978-0-08-043748-4.
3. Ventura RF, Galdino ACM, Viganor L, Schuenck RP, Devereux M, McCann M, Santos ALS, Nunes APF. Antimicrobial action of 1,10-phenanthroline-based compounds on carbapenemase-producing Acinetobacter baumannii clinical strains: efficacy against planktonic- and biofilm-growing cells. Braz. J. Microbiol. 2020; 51(4):1703-1710. https://doi.org/10.1007/s42770-020-00351-9 PMid:32737867 PMCid:PMC7688763
4. Coyle B, Kavanagh K, McCann M, Devereux M, Geraghty M. Mode of anti-fungal activity of 1,10-phenanthroline and its Cu(II), Mn(II) and Ag(I) complexes. Biometals : an international journal on the role of metal ions in biology, biochemistry and medicine 2003; 16(2):321-329. https://doi.org/10.1023/A:1020695923788 PMid:12572690
5. Sigman DS. Mechanisms of DNA Cleavage by Copper-Phenanthroline. J. Am. Chem. Soc. 1990; 112(25):9334-9335.
6. Andrade MF. Antioxidant Activity of Copper-Phenanthroline Complexes. J. Inorg. Biochem. 2000; 80(1):41-49.
7. Eshwika A, Coyle B, Devereux M, McCann M, Kavanagh K. Metal complexes of 1,10-phenanthroline-5,6-dione alter the susceptibility of the yeast Candida albicans to amphotericin B and miconazole. Biometals: an international journal on the role of metal ions in biology, biochemistry, and medicine 2004; 17(4):415-422. https://doi.org/10.1023/B:BIOM.0000029438.97990.c6 PMid:15259362
8. Gandra, RM, Mc Carron P, Fernandes MF, Ramos LS, Mello TP, Aor AC, Branquinha MH, McCann M, Devereux M, Santos ALS. Antifungal Potential of Copper(II), Manganese(II) and Silver(I) 1,10-Phenanthroline Chelates against Multidrug-Resistant Fungal Species Forming the Candida haemulonii Complex: Impact on the Planktonic and Biofilm Lifestyles. Front. microbiol. 2017; 8:1257. https://doi.org/10.3389/fmicb.2017.01257 PMid:28744261 PMCid:PMC5504357
9. Goss C A, Abruna HD. Electrochemical Studies of Phenanthroline and its Metal Complexes. Inorg. Chem. 1985; 24(1):171-176. https://doi.org/10.1021/ic00219a012
10. Kovacs A, Vasas A, Hohmann J. Natural phenanthrenes and their biological activity. Phytochem. 2008; 69(5):1084-1110. https://doi.org/10.1016/j.phytochem.2007.12.005 PMid:18243254
11. Deegan C, Coyle B, McCann M, Devereux M. In vitro antitumour effect of 1,10-phenanthroline-5,6-dione (phendione), [Cu(phendione)3](ClO4)2.4H2O and [Ag(phendione)2]ClO4 using human epithelial cell lines. Chem. -Biol. Interact. 2006; 164(1-2):115-125. https://doi.org/10.1016/j.cbi.2006.08.025 PMid:17030029
12. Viganor L, Howe O, McCarron P, McCann M, Devereux M. The Antibacterial Activity of Metal Complexes Containing 1,10- phenanthroline: Potential as Alternative Therapeutics in the Era of Antibiotic Resistance. Curr. Top. Med. Chem. 2017; 17(11):1280-1302. https://doi.org/10.2174/1568026616666161003143333 PMid:27697043
13. Cujin A, Rudic I, Svenda M. Recent developments in the synthesis and characterization of imidazole derivatives with potential biological activity. Eur. J. Med. Chem. 2017; 126:45-68.
14. Dickeson JE, Summers LA. Derivatives of 1,10-Phenanthroline-5,6-quinone. Aust. J. Chem. 1970; 23(5):1023. https://doi.org/10.1071/CH9701023
15. National Committee for Clinical Laboratory Standards. Performance Standards for Antimicrobial Disk Susceptibility Tests. 5th ed. Approved Standard M2-A5. NCCLS, Villanova, PA; 1993.
16. Lakshmidevi VR., Reeja D, Rajan AR, Vinod B. Advanced Spectrum of Imidazole Derivatives in Therapeutics: A Review. J. Chem. Rev. 2023; 5(3):241-262.
17. Gugwad VM, Yadav YJ, Jadhav PA, Ghanwat AA. Synthesis, Characterization and Investigation of Biological Activities of Some New Zinc Complexes of Imidazo [4,5-f]1,10-phenanthroline Derivatives. Der Pharma Chemica 2017; 9(14):64-76.
18. Reich E, Schibli A. High Performance Thin Layer Chromatography for the Analysis of Medicinal Plants. Thieme Medical Publishers 2007. https://doi.org/10.1055/b-002-66241
19. Bele AA & Khale A. An Overview of Thin Layer Chromatography. Int. J. Pharm. Sci. Res. 2011; 2(2):256-267.
20. Clinical and Laboratory Standards Institute. Methods for dilution antimicrobial susceptibility tests for bacteria that grow aerobically (9th ed.; CLSI document M07-A9). 50 West Valley Road, Suite 2500, Wayne, Pennsylvania; 2012
Published
Abstract Display: 484
PDF Downloads: 461
PDF Downloads: 41 How to Cite
Issue
Section
Copyright (c) 2025 Shahana Salam , Rakesh Kumar Jat

This work is licensed under a Creative Commons Attribution-NonCommercial 4.0 International License.
Authors who publish with this journal agree to the following terms:
- Authors retain copyright and grant the journal right of first publication with the work simultaneously licensed under a Creative Commons Attribution-NonCommercial 4.0 International (CC BY-NC 4.0). that allows others to share the work with an acknowledgment of the work's authorship and initial publication in this journal.
- Authors are able to enter into separate, additional contractual arrangements for the non-exclusive distribution of the journal's published version of the work (e.g., post it to an institutional repository or publish it in a book), with an acknowledgment of its initial publication in this journal.
- Authors are permitted and encouraged to post their work online (e.g., in institutional repositories or on their website) prior to and during the submission process, as it can lead to productive exchanges, as well as earlier and greater citation of published work (See The Effect of Open Access).

.