SYNTHESIS OF 7-(2,3-EPOXYPROPOXY)COUMARIN DERIVATIVES AND EVALUATION OF THEIR RADICAL-SCAVENGING PROPERTIES BY EPR SPECTROSCOPY

Kinga Ostrowska; Alicja Duszek; Magdalena Kołodziejska; Katerina Makarova

doi:10.56782/pps.676

Published : 2025-10-05

No. 2025 (Early Access)

SYNTHESIS OF 7-(2,3-EPOXYPROPOXY)COUMARIN DERIVATIVES AND EVALUATION OF THEIR RADICAL-SCAVENGING PROPERTIES BY EPR SPECTROSCOPY

Kinga Ostrowska

Alicja Duszek

Magdalena Kołodziejska

Katerina Makarova

DOI: https://doi.org/10.56782/pps.676

Abstract

Coumarin derivatives are known for their broad biological activities, particularly their ability to influence oxidative stress pathways. In this work, a new series of 7-(2,3-epoxypropoxy)coumarin derivatives were synthesized and fully characterized by NMR and HRMS. The structural modification introduced a 3’-ethoxy-2’-hydroxypropoxy fragment, and the compounds were evaluated for their ability to modulate hydroxyl and methyl radical formation in the Fenton reaction using Electron Paramagnetic Resonance (EPR) spectroscopy. Comparative analysis revealed that derivatives 1 and its precursor a (6-acetyl-4-methyl-7-(oxiran-2-ylmethoxy)-2H-chromen-2-one) exhibited the most pronounced radical-scavenging activity, demonstrating stronger antioxidant effects than their corresponding substrates. These findings highlight coumarin epoxide derivatives as promising scaffolds for redox-modulating agents and confirm the utility of EPR as a sensitive tool for probing antioxidant potential.

Keywords:

coumarin, Electron Paramagnetic Resonance

Similar Articles

Marta Oleszczuk, NUCLEAR MAGNETIC RESONANCE IN THE STRUCTURAL INVESTIGATION OF BIOMOLECULES: APPLICATION IN THE STUDY OF MODEL HELICAL SYSTEMS , Prospects in Pharmaceutical Sciences: Vol. 4 No. 1 (2006)
Emilia Balcer, Maciej Mazur, GOLD NANOPARTICLES IN THE DIAGNOSTICS AND THERAPY OF CANCER – CHOSEN APPLICATIONS , Prospects in Pharmaceutical Sciences: Vol. 18 No. 1 (2020)
Paulina Jeleniewicz, Zuzanna Czarnocka, Dawid Grzeszczuk, Kinga Ostrowska, SELECTED ASPECTS OF BIOLOGICAL ACTIVITY OF 5-HYDROXYCOUMARIN DERIVATIVES , Prospects in Pharmaceutical Sciences: Vol. 16 No. 1 (2018)
Elżbieta Hejchman, Dominik Lewandowski, SCHIFF BASE COPPER (II) COMPLEXES - NOVEL COMPOUNDS WITH ANTIMICROBIAL ACTIVITY , Prospects in Pharmaceutical Sciences: Vol. 15 No. 9 (2017)
Sylwester Krukowski, SYNTHESIS AND STRUCTURAL STUDIES OF CALCIUM HYDROXYAPATITES MODIFIED WITH AMINO ACIDS , Prospects in Pharmaceutical Sciences: Vol. 11 No. 7 (2013)
Karolina Nowakowska, EPIDEMIOLOGY, CLASSIFICATION AND DIAGNOSIS OF FUNCTIONING AND NONFUNCTIONING PITUITARY ADENOMAS , Prospects in Pharmaceutical Sciences: Vol. 13 No. 6 (2015)
Fatih Islamoğlu, Molecular docking, bioactivity, adme, toxicity risks, and quantum mechanical parameters of some 1,2-dihydroquinoline derivatives were calculated theoretically for investigation of its use as a pharmaceutical active ingredient in the treatment of multiple sclerosis (MS) , Prospects in Pharmaceutical Sciences: Vol. 22 No. 4 (2024)
Swati Pawar, Vishnu P Choudhari, Deepak Jha, Bhanudas Kuchekar, Reshma Jadhav, Isolation and characterization of β-sitosterol and β-citraurin from saponified paprika oleoresin , Prospects in Pharmaceutical Sciences: Vol. 23 No. 1 (2025)

You may also start an advanced similarity search for this article.

Details

References

Statistics

Authors

Download files

PDF

Citation rules

Ostrowska, K., Duszek, A., Kołodziejska, M., & Makarova, K. (2025). SYNTHESIS OF 7-(2,3-EPOXYPROPOXY)COUMARIN DERIVATIVES AND EVALUATION OF THEIR RADICAL-SCAVENGING PROPERTIES BY EPR SPECTROSCOPY. Prospects in Pharmaceutical Sciences, (2025 (Early Access). https://doi.org/10.56782/pps.676

Altmetric indicators

Cited by / Share

Licence

This work is licensed under a Creative Commons Attribution 4.0 International License.

References

1. Annunziata, F.; Pinna, C.; Dallavalle, S.; Tamborini, L.; Pinto, A. An Overview of Coumarin as a Versatile and Readily Accessible Scaffold with Board-Ranging Biological Activities, Int. J. Mol. Sci. 2020, 21, 4618. https://doi.org/10.3390/ijms21134618 DOI: https://doi.org/10.3390/ijms21134618

2. Lacy, A. Studies on Coumarins and Coumarin-Related Compounds to Determine their Therapeutic Role in the Treatment of Cancer, Curr. Pharm. Design. 2004, 10, 3797-3811. https://doi.org/10.2174/13816120433826933 DOI: https://doi.org/10.2174/1381612043382693

3. Hoffmann, C.; Leitz, M.R.; Oberdorf-Maass, S.; Lohse, M.J.; Klotz, K.N. Comparative pharmacology of human ꞵ-adrenergic receptor subtypes - characterization of stably transfected receptors in CHO cells, N-S Arch. Pharmacol. 2004, 369, 151-159. http://doi.org/10.1007/s00210-003-0860-y DOI: https://doi.org/10.1007/s00210-003-0860-y

4. Damu, G.L.V.; Cui, S.F.; Peng, X.M.; Cai, G.X.; Zhou, C.H. Synthesis and bioactive evaluation of a novel series of coumarinazoles, Bioorg. Med. Chem. Lett. 2004, 24, 3605–3608. https://doi.org/10.1016/j.bmcl.2014.05.029 DOI: https://doi.org/10.1016/j.bmcl.2014.05.029

5. Haque, A.S.; Singh, V.; Katiyar, D.; Khan, M.T.A.; Tripathi, V.; Enshasy, A.E.; Pasupuleti, M.; Mishra, B.N. Biotransformation of newly synthesized coumarin derivatives by Candida albicans as potential antibacterial, antioxidant and cytotoxic agents. Process Biochem. 2019, 87, 138-144. https://doi.org/10.1016/j.procbio.2019.08.024 DOI: https://doi.org/10.1016/j.procbio.2019.08.024

6. Gao, Y.; Cheng, H.; Khan, S.; Xiao, G.; Rong, L.; Bai, C. Development of coumarine derivatives as potent anti-filovirus entry inhibitors targeting viral glycoprotein. Eur. J. Med. Chem. 2020 204, 112595. https://doi.org/10.1016/j.ejmech.2020.112595 DOI: https://doi.org/10.1016/j.ejmech.2020.112595

7. Misra, S.; Singh, L.K.; Priyanka, P.; Gupta, J.; Misra-Bhattacharya, S.; Katiyar, D. Synthesis and biological evaluation of 4-oxycoumarin derivatives as a new class of antifilarial agents. Eur. J. Med. Chem. 2015, 94, 211-217. https://doi.org/10.1016/j.ejmech.2015.02.043 DOI: https://doi.org/10.1016/j.ejmech.2015.02.043

8. Priyanka, P.; Misra, S.; Misra-Bhattacharya, S.; Butcher, R.J.; Katiyar, D. Resolution, absolute configuration and antifilarial activity of coumarinyl amino alcohols. Tetrahedron Asymmetr. 2017, 28, 734–743. https://doi.org/10.1016/j.tetasy.2017.04.005 DOI: https://doi.org/10.1016/j.tetasy.2017.04.005

9. Kossakowski, J.; Zawadowski, T.; Suski, S. Synthesis of aminopropanol derivatives of 7-ethoxy-8-hydroxy- and 6,7-diethoxy-8-hydroxy-2H-1-benzopyran-2-one with an expected ꞵ-adrenolytic activity. Acta Polon. Pharm. 1998, 55, 77-79.

10. Zawadowski, T.; Kossakowski, J. Synteza aminoalkanolowych pochodnych 8-hydroksy-7-metoksy-2H-1-benzopiran-2-onu o spodziewanym działaniu ꞵ-adrenolitycznym. Acta Polon. Pharm. 1993, 50, 269-273.

11. Chen, Y.L.; Wang, T.C.; Lee, K.H.; Tzeng, C.C.; Chang, Y.L.; Teng, C.M. Synthesis of Coumarin Derivatives as Inhibitors of Platelet Aggregation. Helv. Chim. Acta 1996, 79, 651-657. https://doi.org/10.1002/hlca.19960790308 DOI: https://doi.org/10.1002/hlca.19960790308

12. Farag, N.A.; Mohamed, S.R.; Soliman, G.A.H. Design, synthesis, and docking studies of novel benzopyrone derivatives as H1-antihistaminic agents. Bioorg. Med. Chem. 2008, 16, 9009–9017. https://doi.org/10.1016/j.bmc.2008.08.039 DOI: https://doi.org/10.1016/j.bmc.2008.08.039

13. Wang, G.; Wang, J.; He, D.; Li, X.; Peng, Z. One-pot and three-component synthesis characterization and biological evaluation of some new 1,2,4-triazine-coumarins. Heterocycles 2016, 92, 1430-1439. https://doi.org/10.3987/com-16-13491 DOI: https://doi.org/10.3987/COM-16-13491

14. Srivastava, P.; Vyas, V.K.; Variya, B.; Patel, P.N.; Qureshi, G.A.; Ghate, M. Synthesis, anti-inflammatory, analgesic, 5-lipoxygenase (5-LOX) inhibition activities, and molecular docking study of 7-substituted coumarin derivatives. Bioorg. Chem. 2016, 67, 130–138. https://doi.org/10.1016/j.bioorg.2016.06.004 DOI: https://doi.org/10.1016/j.bioorg.2016.06.004

15. Ostrowska, K.; Ciesielski, A.; Sadocha, A.; Prokopiuk, D.; Trzaskowski, B. A detailed structural analysis of selected (oxiran-2-yl)methoxy- and 3-chloro-2-hydroxypropoxycoumarin. J. Mol. Struct. 2025, 1321, 140269. https://doi.org/10.1016/j.molstruc.2024.140269 DOI: https://doi.org/10.1016/j.molstruc.2024.140269

16. Ostrowska, K.; Horosz, G.; Kruk, K.; Sieroń, B.; Leśniak, A.; Czartoryska, Z.; Bujalska-Zadrożny, M.; Milenkovic, D.; Trzaskowski, B.; Exploring the Potential of Coumarin Derivatives on Serotonin Receptors 5-HT1A and 5-HT2A, Int. J. Mol. Sci. 2025, 26, 1946, https://doi.org/10.3390/ijms26051946 DOI: https://doi.org/10.3390/ijms26051946

Kinga Ostrowska

kostrowska@wum.edu.pl

Affiliation:

a:1:{s:5:"en_US";s:120:"Department of Organic and Physical Chemistry, Faculty of Pharmacy, Medical University of Warsaw, 02-097 Warsaw, Poland. ";} Poland

Alicja Duszek

alicja.duszek24@gmail.com

Bio Statement (e.g., department and rank)

Department of Organic and Physical Chemistry, Faculty of Pharmacy, Medical University of Warsaw, 02-097 Warsaw, Poland.

Magdalena Kołodziejska

s082139@student.wum.edu.pl

Bio Statement (e.g., department and rank)

Department of Organic and Physical Chemistry, Faculty of Pharmacy, Medical University of Warsaw, 02-097 Warsaw, Poland.

Katerina Makarova

katerina.makarova@wum.edu.pl

Bio Statement (e.g., department and rank)

Department of Organic and Physical Chemistry, Faculty of Pharmacy, Medical University of Warsaw, 02-097 Warsaw, Poland.

SYNTHESIS OF 7-(2,3-EPOXYPROPOXY)COUMARIN DERIVATIVES AND EVALUATION OF THEIR RADICAL-SCAVENGING PROPERTIES BY EPR SPECTROSCOPY

Kinga Ostrowska

Alicja Duszek

Magdalena Kołodziejska

Katerina Makarova

Abstract

Keywords:

Most read articles by the same author(s)

Similar Articles

Kinga Ostrowska

Alicja Duszek

Magdalena Kołodziejska

Katerina Makarova