Synthesis, Identification, and Biological Evaluation of new coumarin-pyrazoline Derivatives as Anti-oxidant Agents
DOI:
https://doi.org/10.21123/bsj.2024.8978Keywords:
ABTS assay, Antioxidants compounds, Ascorbic acid, Coumarin- pyrazoline derivatives, Hybrid coumarin.Abstract
The coumarin scaffold was combined with nitrogen containing heteroatom molecule known as pyrazoline to increase its biological activity, and it demonstrated a wide range of activity. The study involved the synthesis of a new compound by condensation method, and the structural structures of the prepared compounds were characterized using spectroscopic and analytical studies FT-IR, 1H-NMR,13CNMR, and mass spectrometry, through which it was proven that pyrazoline ring through the appearance of protons of the methylene group in different coupling constants. On the other hand, the proton of C11’, adapts to two different adjacent angles for the two protons of the methylene group, so the coupling constant of the protons adjacent to each other is different, and the bidirectional angle between the protons can be related to the karplus relationship with the adjacent proton coupling constant. The biological activity of the prepared compounds was studied using the principle of ABTS•+ assay depended on the generation of the blue/green ABTS•+ chromophore by the reaction between ABTS and potassium persulfate at about 734 nm, as the results of its effectiveness showed the results show that coumarin-pyrazoline derivatives are characterized by high antioxidant activity that is superior to ascorbic acid, especially the dimethylamine derivative.
Received 20/04/2024
Revised 23/10/2023
Accepted 25/10/2023
Published Online First 20/07/2024
References
Akkol EK, Genç Y, Karpuz B, Sobarzo-Sánchez E, Capasso R. Coumarins and coumarin-related compounds in pharmacotherapy of cancer. Cancers (Basel). 2020; 12(7): 1-25. https://doi.org/10.3390/cancers1207195
Egan D, O’kennedy R, Moran E, Cox D, Prosser E, Thornes RD. The pharmacology, metabolism, analysis, and applications of coumarin and coumarin-related compounds. Drug Metab Rev.1990; 22(5): 503-529. https://doi.org/10.3109/03602539008991449.
Al- Zobaydi SF, Al-Hammed KA, Ismael BD. Synthesis and Characterization of 3 - Substituted Coumarin. Baghdad Sci J. 2016; 13(1): 0089. https://doi.org/10.21123/bsj.2016.13.1.0089
Peng XM, Damu GL V, Zhou CH. Review: Developments of Coumarin Compounds in Medicinal Chemistry. Curr Pharm Des. 2013; 19: 3884-3930. https://doi.org/10.2174/1381612811319210013
Singh H, Singh JV, Bhagat K, Kaur Gulati H, Sanduja M, Kumar N et al., Rational approaches, design strategies, structure activity relationship and mechanistic insights for therapeutic coumarin hybrids. Bioorganic Med Chem. 2019; 27(16): 3477-3510. http://doi.10.1016/j.bmc.2019.06.033
Akkol EK, Genç Y, Karpuz B, Sobarzo-Sánchez E, Capasso R. Coumarins and coumarin-related compounds in pharmacotherapy of cancer. Cancers (Basel). 2020; 12(7): 1-25. https://doi.org/10.3390/cancers12071959
Lacy A. Studies on Coumarins and Coumarin-Related Compounds to Determine their Therapeutic Role in the Treatment of Cancer. Curr Pharm Des. 2005; 10(30): 3797-3811.http://doi.org/10.2174/1381612043382693
Sharifi-Rad J, Cruz-Martins N, López-Jornet P, Harun N, Yeskaliyeva B, Beyatli A et al., Natural Coumarins: Exploring the Pharmacological Complexity and Underlying Molecular Mechanisms. Oxid Med Cell Longev. 2021; Aug 23: 6492346.https://doi.org/10.1155/2021/6492346
Tsivileva OM, Koftin OV, and Evseeva NV. Coumarins as Fungal Metabolites with Potential Medicinal Properties. Antibiotics (Basel). 2022 Sep; 11(9): 1156. https://doi.org/10.3390/antibiotics11091156
Patel G, Banerjee S. Review on Synthesis of Bio-active Coumarin-fused Heterocyclic Molecules. Curr Org Chem. 2020; 24(22): 2566-2587. http://doi.org/10.2174/1385272824999200709125717
Nepali K, Sharma S, Sharma M, Bedi PMS, Dhar KL. Rational approaches, design strategies, structure activity relationship and mechanistic insights for anticancer hybrids. Eur J Med Chem. 2014; 77: 422-487.
Pasricha S, Gahlot P. Synthetic Strategies and Biological Potential of Coumarin-Chalcone Hybrids: A New Dimension to Drug Design. Curr Org Chem. 2020; 24(4): 402-438. http://doi.org/10.2174/1385272824666200219091830
Rawat A, Vijaya Bhaskar Reddy A. Recent advances on anticancer activity of coumarin derivatives. Eur J Med Chem Reports. 2022; 5 Feb: 100038. http://doi./10.1016/j.ejmcr.2022.100038
Nehra B, Rulhania S, Jaiswal S, Kumar B, Singh G, Monga V. Recent Advancements in the Development of Bioactive Pyrazoline Derivatives. Eur J Med Chem. Published online 2020: 112666. https://doi.org/10.1016/j.ejmech.2020.112666
Bashir MK, Al-omari NA wahhab, Omar AO. Glucose conjugation of coumarin-pyrazoline derivatives as a promising strategy for cancer cell targeting. 2019 . https://api.semanticscholar.org/CorpusID:212509444
Sandhu S, Bansal Y, Silakari O, Bansal G. Coumarin hybrids as novel therapeutic agents. Bioorganic Med Chem. 2014; 22(15): 3806-3814. https://doi.org/10.1016/j.bmc.2014.05.032
Annunziata F, Pinna C, Dallavalle S, Tamborini L and Pinto A. Review : An Overview of Coumarin as a Versatile and Readily Accessible Scaffold with Broad-Ranging Biological Activities. Int J Mol Sci. 2020; 21(13): 4618. https://doi.org/10.3390/ijms21134618
Al-Awad SM, Raheem LA, Jaccob AA. Synthesis and pharmacological evaluation of novel coumarin derivatives. Int J Res Pharm Sci. 2020; 11(1) :865-874. http://doi.org/10.26452/ijrps. v11i1.1908
Ahmed MH, El-Hashash MA, Marzouk MI, El-Naggar AM. Design, Synthesis, and Biological Evaluation of Novel Pyrazole, Oxazole, and Pyridine Derivatives as Potential Anticancer Agents Using Mixed Chalcone. J Heterocycl Chem. 2019; 56(1): 114-123. https://doi.org/10.1002/jhet.3380
Patel M, Pandey N, Timaniya J, Parikh P, Jain CN and Patel K. Coumarin–carbazole based functionalized pyrazolines: synthesis, characterization, anticancer investigation and molecular docking. RSC Adv. 2021; 11: 27627.https://doi.org/10. 1039/d1ra03970a
Al-naseeri AKA. Synthesis and Characterization of Some New Pyrazoline and Isoxazoline Derivatives as Antibacterial Agents, Baghdad Sci J. 2016; 13(3): 568-577. https://doi.org/10.21123/bsj.2016.13.3.0568
Çelik G, Arslan T, Şentürk M, Ekinci D. Synthesis and characterization of some new pyrazolines and their inhibitory potencies against carbonic anhydrases. Arch Pharm (Weinheim). 2020; 353(3): 4-9. https://doi.org/10.1002/ardp.201900292
Saroja T, Ezhilarasi RM, Selvamani V, Mahalakshmi S. Synthesis, Characterization and In-Silico Analysis of New 2-Pyrazolines. J Sci Res. 2021; 13(1):183-194. https://doi.org/10.3329/jsr.v13i1.46995
Patel M, Pandey N, Timaniya J, Parikh P, Chauhan, A Jain N et al., Coumarin-carbazole based functionalized pyrazolines: Synthesis, characterization, anticancer investigation and molecular docking. RSC Adv. 2021; 11(44): 27627-27644. https://doi.org/10.1039/D1RA03970A
Patel J. Microwave assisted synthesis, characterization and antimicrobial evaluation of pyrazolyl and pyrazoline substituted coumarins. Int J Res Anal Rev. 2019; 6(1): 385-404. www.ijrar.org (E-ISSN 2348-1269, P- ISSN 2349-5138)
Mustafa G. Synthesis and Antioxidant Activity of a Novel Series of Pyrazolotriazine, Coumarin, Oxoazinone, and Pyrazinopyrimidine Derivatives. Arch Pharm Chem Life Sci. 2013; 346: 1–9. https://doi.org/10.1002/ardp.201300128
Mustafa YF, Sarah AW, Sara FJ, Rahma MJ et al., A Narrative Review of Benzo-Fused Coumarins, Shedding Light on Their Medicinal Activities.Iraqi J Pharm. 20(1) (2023) 07-14. https://doi.org/10.33899/iphr.2023.138286.1024
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