Coumarin Based Analogues, a Vivid Terrace for Developing Oncology Medications

Authors

  • Dr. Pratap Chandra Pradhan Director, Mothers’ Group of Institution, Institute of Pharmaceutical Sciences, Jaleswar, Balasore, Odisha, 756032, India
  • Subhajit Makar Assistant Professor, Department of Pharm. Chem., Institute of Pharmaceutical Sciences, Jaleswar, Balasore, Odisha, 756032, India
  • Hemanta Kumar Khatua Assistant Professor, Department of Pharm. Chem., Institute of Pharmaceutical Sciences, Jaleswar, Balasore, Odisha, 756032, India
  • Gargi Pal Assistant Professor, Department of Pharmaceutics, Institute of Pharmaceutical Sciences, Jaleswar, Balasore, Odisha, 756032, India

Keywords:

Coumarins, Cancer, Chromone, Synthesis, Topoisomerase, Triazole, Halo coumarin, Quinone, Aromatase

Abstract

Coumarins are found in higher plants like Rutaceae and Umbelliferae and essential oils of cinnamon bark, cassia leaf, and lavender oil. It shows different biological properties, viz antimicrobial, antibacterial, antifungal, antioxidant, antitumor, anti-HIV, antihypertension, anticoagulant, anticancer, antiviral, anti-inflammatory, analgesics, antidiabetic, anti-depressive, and other bioactive properties. Despite numerous effects of coumarins in the search for bioactive compounds, they remain as one of the most versatile class of compounds for anticancer drug design and discovery. Coumarin and its derivatives possess anticancer activity against different types of cancers such as prostate, renal, breast, laryngeal, lung, colon, CNS, leukemia, malignant melanoma. In this review, current developments of coumarin-based anticancer agents viz simple coumarin, furanocoumarin, pyranocoumarin, pyrone-substituted coumarin, and their important derivatives have been discussed. The coumarin-triazole, coumarin-chalcone, coumarin-thiosemicarbazone derivatives, and coumarin-metal complexes have been found more potent than coumarin. Hence, further study and structural improvement on coumarin and its derivatives may lead to the design and development of more potent anticancer agents.

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References

Han, X., Luo, J., Wu, F., Hou, X., Yan, G., Zhou, M., ... & Li, R. (2016). Synthesis and biological evaluation of novel 2, 3-dihydrochromeno [3, 4-d] imidazol-4 (1H)-one derivatives as potent anticancer cell proliferation and migration agents. European journal of medicinal chemistry, 114, 232-243.

Imran, M., Bawadekji, A., & Nayeem, N. (2019). Preparation And In Vitro Anticancer Activity Evaluation Of‎ Some Coumarin Derivatives. Pharmacophore, 10(4-2019), 8-14.

Nikhil, B., Shikha, B., & Prakash, N. B. (2012). Diverse pharmacological activities of 3-substituted coumarins: a review. The International Research Journal of Pharmacy, 3(7), 17-22.

Stefanachi, A., Leonetti, F., Pisani, L., Catto, M., & Carotti, A. (2018). Coumarin: A natural, privileged and versatile scaffold for bioactive compounds. Molecules, 23(2), 250.

Pelkonen, O., Raunio, H., Rautio, A., Pasanen, M., & Lang, M. (1997). The metabolism of coumarins: In; Coumarins: Biology, Applications and mode of action. Wiley.

Saidu, N. E. B., Valente, S., Bana, E., Kirsch, G., Bagrel, D., & Montenarh, M. (2012). Coumarin polysulfides inhibit cell growth and induce apoptosis in HCT116 colon cancer cells. Bioorganic & medicinal chemistry, 20(4), 1584-1593.

Geisler, J., Sasano, H., Chen, S., & Purohit, A. (2011). Steroid sulfatase inhibitors: promising new tools for breast cancer therapy? The Journal of Steroid Biochemistry and Molecular Biology, 125(1-2), 39-45.

Lin, M. H., Cheng, C. H., Chen, K. C., Lee, W. T., Wang, Y. F., Xiao, C. Q., & Lin, C. W. (2014). Induction of ROS-independent JNK-activation-mediated apoptosis by a novel coumarin-derivative, DMAC, in human colon cancer cells. Chemico-Biological Interactions, 218, 42-49.

De, S. K., & Gibbs, R. A. (2005). An efficient and practical procedure for the synthesis of 4-substituted coumarins. Synthesis, 2005(08), 1231-1233.

Gadakh, S. K., Dey, S., & Sudalai, A. (2015). Rh-catalyzed synthesis of coumarin derivatives from phenolic acetates and acrylates via C–H bond activation. The Journal of organic chemistry, 80(22), 11544-11550.

Cervi, A., Vo, Y., Chai, C. L., Banwell, M. G., Lan, P., & Willis, A. C. (2020). Gold (I)-Catalyzed Intramolecular Hydroarylation of Phenol-Derived Propiolates and Certain Related Ethers as a Route to Selectively Functionalized Coumarins and 2 H-Chromenes. The Journal of Organic Chemistry, 86(1), 178-198.

Qian, H., & Sun, J. (2021). Synthesis of coumarins via [4+ 2] cyclization of siloxy alkynes and salicylaldehydes. Synlett, 32(02), 207-210.

Moazzam, A., Khodadadi, M., Jafarpour, F., & Ghandi, M. (2022). Dual role of oxoaldehydes: Divergent synthesis of 3-aryl-and 3-aroylcoumarins. The Journal of Organic Chemistry, 87(5), 3630-3637.

Chauhan, S., Kumar, A. S., & Swamy, K. K. (2023). δ-Acetoxy allenoate as a 5C-synthon in domino-annulation with sulfamidate imines: ready access to coumarins. The Journal of Organic Chemistry, 88(17), 12432-12444.

Wang, Y., Wang, S., Chen, B., Li, M., Hu, X., Hu, B., ... & Shen, Z. (2020). Visible-light-induced arene C (sp2)–H lactonization promoted by DDQ and tert-butyl nitrite. Synlett, 31(03), 261-266.

Kashyap, A., Singh, P. P., Murti, Y., Gahtori, P., Mahajan, S., Kandhari, H., ... & Srivastava, V. (2024). Visible-light photocatalysed synthesis of coumarin derivatives. Tetrahedron Letters, 142, 155099.

Wu, Y., Xu, J., Liu, Y., Zeng, Y., & Wu, G. (2020). A review on anti-tumor mechanisms of coumarins. Frontiers in oncology, 10, 592853.

Correa de Moraes, M., Frassini, R., Roesch-Ely, M., Reisdorfer de Paula, F., & Barcellos, T. (2024). Novel Coumarin–Nucleobase Hybrids with Potential Anticancer Activity: Synthesis, In Vitro Cell-Based Evaluation, and Molecular Docking. Pharmaceuticals, 17(7), 956.

Mustafa, Y. F., Hassan, D. A., Faisal, A. F., & Alshaher, M. M. (2024). Synthesis of novel skipped diene-3-halocoumarin conjugates as potent anticancer and antibacterial biocompatible agents. Results in Chemistry, 11, 101846.

Rubab, L., Afroz, S., Ahmad, S., Hussain, S., Nawaz, I., Irfan, A., ... & Mojzych, M. (2022). An update on synthesis of coumarin sulfonamides as enzyme inhibitors and anticancer agents. Molecules, 27(5), 1604.

Ibrar, A., Zaib, S., Jabeen, F., Iqbal, J., & Saeed, A. (2016). Unraveling the alkaline phosphatase inhibition, anticancer, and antileishmanial potential of coumarin–triazolothiadiazine hybrids: design, synthesis, and molecular docking analysis. Archiv der Pharmazie, 349(7), 553-565.

Sinha, S., Kumaran, A. P., Mishra, D., & Paira, P. (2016). Synthesis and cytotoxicity study of novel 3-(triazolyl) coumarins based fluorescent scaffolds. Bioorganic & Medicinal Chemistry Letters, 26(22), 5557-5561.

Alshabanah, L. A., Al-Mutabagani, L. A., Gomha, S. M., & Ahmed, H. A. (2022). Three-component synthesis of some new coumarin derivatives as anticancer agents. Frontiers in Chemistry, 9, 762248.

Chen, S., Cho, M., Karlsberg, K., Zhou, D., & Yuan, Y. C. (2004). Biochemical and biological characterization of a novel anti-aromatase coumarin derivative. Journal of Biological Chemistry, 279(46), 48071-48078.

Leonetti, F., Favia, A., Rao, A., Aliano, R., Paluszcak, A., Hartmann, R. W., & Carotti, A. (2004). Design, synthesis, and 3D QSAR of novel potent and selective aromatase inhibitors. Journal of medicinal chemistry, 47(27), 6792-6803.

Stefanachi, A., Favia, A. D., Nicolotti, O., Leonetti, F., Pisani, L., Catto, M., ... & Carotti, A. (2011). Design, Synthesis, and Biological Evaluation of Imidazolyl Derivatives of 4, 7-Disubstituted Coumarins as Selective Aromatase Inhibitors. JOURNAL OF MEDICINAL CHEMISTRY, 54, 1625-1643.

Hussain, M. K., Ansari, M. I., Yadav, N., Gupta, P. K., Gupta, A. K., Saxena, R., ... & Hajela, K. (2014). Design and synthesis of ERα/ERβ selective coumarin and chromene derivatives as potential anti-breast cancer and anti-osteoporotic agents. RSC Advances, 4(17), 8828-8845.

Valente, S., Bana, E., Viry, E., Bagrel, D., & Kirsch, G. (2010). Synthesis and biological evaluation of novel coumarin-based inhibitors of Cdc25 phosphatases. Bioorganic & medicinal chemistry letters, 20(19), 5827-5830.

Saidu, N. E. B., Valente, S., Bana, E., Kirsch, G., Bagrel, D., & Montenarh, M. (2012). Coumarin polysulfides inhibit cell growth and induce apoptosis in HCT116 colon cancer cells. Bioorganic & medicinal chemistry, 20(4), 1584-1593.

Zhang, W., Li, Z., Zhou, M., Wu, F., Hou, X., Luo, H., ... & Li, R. (2014). Synthesis and biological evaluation of 4-(1, 2, 3-triazol-1-yl) coumarin derivatives as potential antitumor agents. Bioorganic & medicinal chemistry letters, 24(3), 799-807.

Bana, E., Sibille, E., Valente, S., Cerella, C., Chaimbault, P., Kirsch, G., ... & Bagrel, D. (2015). A novel coumarin‐quinone derivative SV37 inhibits CDC25 phosphatases, impairs proliferation, and induces cell death. Molecular carcinogenesis, 54(3), 229-241.

Neelgundmath, M., Dinesh, K. R., Mohan, C. D., Li, F., Dai, X., Siveen, K. S., ... & Kotresh, O. (2015). Novel synthetic coumarins that targets NF-κB in Hepatocellular carcinoma. Bioorganic & medicinal chemistry letters, 25(4), 893-897.

Fayed, E. A., Sabour, R., Harras, M. F., & Mehany, A. B. (2019). Design, synthesis, biological evaluation and molecular modeling of new coumarin derivatives as potent anticancer agents. Medicinal Chemistry Research, 28, 1284-1297.

Manidhar, D. M., Kesharwani, R. K., Reddy, N. B., Reddy, C. S., & Misra, K. (2013). Designing, synthesis, and characterization of some novel coumarin derivatives as probable anticancer drugs. Medicinal Chemistry Research, 22, 4146-4157.

Al-Wahaibi, L. H., Abu-Melha, H. M., & Ibrahim, D. A. (2018). Synthesis of Novel 1, 2, 4‐Triazolyl Coumarin Derivatives as Potential Anticancer Agents. Journal of Chemistry, 2018(1), 5201374.

Vaarla, K., Karnewar, S., Panuganti, D., Peddi, S. R., Vedula, R. R., Manga, V., & Kotamraju, S. (2019). 3‐(2‐(5‐Amino‐3‐aryl‐1H‐pyrazol‐1‐yl) thiazol‐4‐yl)‐2H‐chromen‐2‐ones as Potential Anticancer Agents: Synthesis, Anticancer Activity Evaluation and Molecular Docking Studies. ChemistrySelect, 4(14), 4324-4330.

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Published

21-03-2025

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How to Cite

Pradhan , P. C., Makar, S., Khatua , H. K., & Pal, G. (2025). Coumarin Based Analogues, a Vivid Terrace for Developing Oncology Medications. International Journal of Innovative Scientific Research, 3(1), 144-156. https://ijisr.net/ijisr/article/view/68