Enaminones as Building Blocks in Heterocyclic Synthesis: Novel Routs for Synthesis of Coumarin Analogs and Study their Anticancer Activities

References

• S. Sidney, A. S. Go, and J. S. Rana, “Transition from Heart Disease to Cancer as the Leading Cause of Death in the United States,” Annals of Internal Medicine 171, no. 3 (2019): 225. doi:10.7326/L19-0202
   PubMed Web of Science ®Google Scholar
• B. N. Marak, J. Dowarah, L. Khiangte, and V. P. Singh, “A Comprehensive Insight on the Recent Development of Cyclic Dependent Kinase Inhibitors as Anticancer Agents,” European Journal of Medicinal Chemistry 203 (2020): 112571. doi:10.1016/j.ejmech.2020.112571
   PubMed Web of Science ®Google Scholar
• Z. Huang, B. Zhao, Z. Qin, Y. Li, T. Wang, W. Zhou, J. Zheng, S. Yang, Y. Shi, Y. Fan, et al, “Novel Dual Inhibitors Targeting CDK4 and VEGFR2 Synergistically Suppressed Cancer Progression and Angiogenesis,” European Journal of Medicinal Chemistry 181 (2019): 111541. doi:10.1016/J.EJMECH.2019.07.044
   PubMed Web of Science ®Google Scholar
• Y. Wan, Y. Li, C. Yan, M. Yan, and Z. Tang, “Indole: A Privileged Scaffold for the Design of Anti-Cancer Agents,” European Journal of Medicinal Chemistry 183 (2019): 111691. doi:10.1016/j.ejmech.2019.111691
   PubMed Web of Science ®Google Scholar
• E. K. Akkol, Y. Genç, B. Karpuz, E. Sobarzo-Sánchez, and R. Capasso, “Coumarins and Coumarin-Related Compounds in Pharmacotherapy of Cancer,” Cancers (Cancers 12, no. 7 (2020): 1959. doi:10.3390/cancers12071959
   PubMed Web of Science ®Google Scholar
• M. B. Yerer, S. Dayan, M. I. Han, A. Sharma, H. S. Tuli, and K. Sak, “Nanoformulations of Coumarins and the Hybrid Molecules of Coumarins with Potential Anticancer Effects,” Anti-Cancer Agents in Medicinal Chemistry 20, no. 15 (2020): 1797–816. doi:10.2174/1871520620666200310094646
   PubMed Web of Science ®Google Scholar
• K. N. Venugopala, V. Rashmi, and B. Odhav, “Review on Natural Coumarin Lead Compounds for Their Pharmacological Activity,” Biomed Research International. 2013 (2013): 1–14. doi:10.1155/2013/963248
   Web of Science ®Google Scholar
• B. Bibak, F. Shakeri, G. E. Barreto, Z. Keshavarzi, T. Sathyapalan, and A. Sahebkar, “A Review of the Pharmacological and Therapeutic Effects of Auraptene,” BioFactors (Oxford, England) 45, no. 6 (2019): 867–79. doi:10.1002/biof.1550
   PubMed Web of Science ®Google Scholar
• J. J. Zhu, and J. G. Jiang, “Pharmacological and Nutritional Effects of Natural Coumarins and Their Structure–Activity Relationships,” Molecular Nutrition & Food Research 62, no. 14 (2018): 1701073. doi:10.1002/mnfr.201701073
   Web of Science ®Google Scholar
• J. R. S. Hoult, and M. Payá, “Pharmacological and Biochemical Actions of Simple Coumarins: Natural Products with Therapeutic Potential,” General Pharmacology 27, no. 4 (1996): 713–22. doi:10.1016/0306-3623(95)02112-4
   PubMedGoogle Scholar
• F. Annunziata, C. Pinna, S. Dallavalle, L. Tamborini, and A. Pinto, “An Overview of Coumarin as a Versatile and Readily Accessible Scaffold with Broad-Ranging Biological Activities,” International Journal of Molecular Sciences 21, no. 13 (2020): 4618. doi:10.3390/ijms21134618
   PubMed Web of Science ®Google Scholar
• M. Lončar, M. Jakovljević, D. Šubarić, M. Pavlić, V. Buzjak Služek, I. Cindrić, and M. Molnar, “Coumarins in Food and Methods of Their Determination,” Foods 9, no. 5 (2020): 645. doi:10.3390/foods9050645
   PubMed Web of Science ®Google Scholar
• A. Abdel-Aziem, and A. O. Abdelhamid, “Synthesis of Coumarin Analogues Clubbed 1,3,4-Thiadiazine or Thiazole and Their Anticancer Activity,” Polycyclic Aromatic Compounds 42 (2021): 7310–20. doi:10.1080/10406638.2021.1998152
   Web of Science ®Google Scholar
• H. L. Qin, Z. W. Zhang, L. Ravindar, and K. P. Rakesh, “Antibacterial Activities with the Structure-Activity Relationship of Coumarin Derivatives,” European Journal of Medicinal Chemistry 207 (2020): 112832. doi:10.1016/j.ejmech.2020.112832
   PubMed Web of Science ®Google Scholar
• C. Liang, W. Ju, S. Pei, Y. Tang, and Y. Xiao, “Pharmacological Activities and Synthesis of Esculetin and Its Derivatives: A Mini-Review,” Journal of Lipid Research. 22, no. 3 (2017): 387. doi:10.3390/molecules22030387
   Google Scholar
• M. O. Sarhan, S. S. Abd El-Karim, M. M. Anwar, R. H. Gouda, W. A. Zaghary, and M. A. Khedr, “Discovery of New Coumarin-Based Lead with Potential Anticancer, cdk4 Inhibition and Selective Radiotheranostic Effect: Synthesis, 2d & 3d Qsar, Molecular Dynamics, in Vitro Cytotoxicity, Radioiodination, and Biodistribution Studies,” Molecules 26, no. 8 (2021): 2273. doi:10.3390/molecules26082273
   PubMed Web of Science ®Google Scholar
• Z. Tayarani-Najaran, N. Tayarani-Najaran, and S. Eghbali, “A Review of Auraptene as an Anticancer Agent,” Frontiers in Pharmacology 12, (2021): 1–9. doi:10.3389/fphar.2021.698352
   Web of Science ®Google Scholar
• T. Al-Warhi, A. Sabt, E. B. Elkaeed, and W. M. Eldehna, “Recent Advancements of Coumarin-Based Anticancer Agents: An up-to-Date Review,” Bioorganic Chemistry 103 (2020): 104163. doi:10.1016/J.BIOORG.2020.104163
   PubMed Web of Science ®Google Scholar
• N. Bhattarai, A. A. Kumbhar, Y. R. Pokharel, and P. N. Yadav, “Anticancer Potential of Coumarin and Its Derivatives,” Mini-Reviews in Medicinal Chemistry 21, no. 19 (2021): 2996–3029. doi:10.2174/1389557521666210405160323
   PubMed Web of Science ®Google Scholar
• B. Z. Kurt, N. Ozten Kandas, A. Dag, F. Sonmez, and M. Kucukislamoglu, “Synthesis and Biological Evaluation of Novel Coumarin-Chalcone Derivatives Containing Urea Moiety as Potential Anticancer Agents,” Arabian Journal of Chemistry 13, no. 1 (2020): 1120–9. doi:10.1016/j.arabjc.2017.10.001
   Web of Science ®Google Scholar
• S. K. Ramadan, and S. A. Rizk, “Synthesis, Density Functional Theory, and Cytotoxic Activity of Some Heterocyclic Systems Derived from 3-(3-(1,3-Diphenyl-1H-Pyrazol-4-yl)Acryloyl)-2H-Chromen-2-One,” Journal of the Iranian Chemical Society 19, no. 1 (2022): 187–201. doi:10.1007/s13738-021-02298-6
   Web of Science ®Google Scholar
• A. Thakur, R. Singla, and V. Jaitak, “Coumarins as Anticancer Agents: A Review on Synthetic Strategies, Mechanism of Action and SAR Studies,” European Journal of Medicinal Chemistry. 101 (2015): 476–95. doi:10.1016/j.ejmech.2015.07.010
   PubMed Web of Science ®Google Scholar
• A. M. El-Naggar, M. M. Hemdan, and S. R. Atta-Allah, “An Efficient One-Pot Synthesis of New Coumarin Derivatives as Potent Anticancer Agents under Microwave Irradiation,” Journal of Heterocyclic Chemistry 54, no. 6 (2017): 3519–26. doi:10.1002/jhet.2975
   Web of Science ®Google Scholar
• X. Wang, H. Zhou, X. Wang, K. Lei, and S. Wang, “Coumarin Derivatives with Potential Antidepressant Effects,” Published Online (2021).
   Google Scholar
• S. Weigt, N. Huebler, R. Strecker, T. Braunbeck, and T. H. Broschard, “Developmental Effects of Coumarin and the Anticoagulant Coumarin Derivative Warfarin on Zebrafish (Danio rerio) Embryos,” Reproductive Toxicology (Elmsford, NY) 33, no. 2 (2012): 133–41. doi:10.1016/j.reprotox.2011.07.001
   PubMed Web of Science ®Google Scholar
• B. M. Bizzarri, L. Botta, E. Capecchi, I. Celestino, P. Checconi, A. T. Palamara, L. Nencioni, and R. Saladino, “Regioselective IBX-Mediated Synthesis of Coumarin Derivatives with Antioxidant and anti-Influenza Activities,” Journal of Natural Products 80, no. 12 (2017): 3247–54. doi:10.1021/acs.jnatprod.7b00665
   PubMed Web of Science ®Google Scholar
• K. I. Bhat, A. Kumar, and P. Kumar, “Synthesis, Cytotoxic and Antihyperlipidemic Activities of Some New Coumarinyl 4-Thiazolidinone Derivatives,” Indian Journal of Pharmaceutical Education and Research 55, no. 3s (2021): S807–S813. doi:10.5530/ijper.55.3s.188
   Google Scholar
• C. A. Kontogiorgis, K. Savvoglou, and D. J. Hadjipavlou-Litina, “Antiinflammatory and Antioxidant Evaluation of Novel Coumarin Derivatives,” Journal of Enzyme Inhibition and Medicinal Chemistry 21, no. 1 (2006): 21–9. doi:10.1080/14756360500323022
   PubMed Web of Science ®Google Scholar
• K. Pérez-Cruz, M. Moncada-Basualto, J. Morales-Valenzuela, G. Barriga-González, P. Navarrete-Encina, L. Núñez-Vergara, J. A. Squella, and C. Olea-Azar, “Synthesis and Antioxidant Study of New Polyphenolic Hybrid-Coumarins,” Arabian Journal of Chemistry 11, no. 4 (2018): 525–37. doi:10.1016/j.arabjc.2017.05.007
   Web of Science ®Google Scholar
• Y. K. Al-Majedy, D. L. Al-Duhaidahawi, K. F. Al-Azawi, A. A. Al-Amiery, A. A. H. Kadhum, and A. B. Mohamad, “Coumarins as Potential Antioxidant Agents Complemented with Suggested Mechanisms and Approved by Molecular Modeling Studies,” Molecules 21, no. 2 (2016): 135. doi:10.3390/molecules21020135
   PubMed Web of Science ®Google Scholar
• C. P. Kaushik, and M. Chahal, “Synthesis, Antimalarial and Antioxidant Activity of Coumarin Appended 1,4-Disubstituted 1,2,3-Triazoles,” Monatshefte Für Chemie - Chemical Monthly 152, no. 8 (2021): 1001–12. doi:10.1007/s00706-021-02821-8
   Google Scholar
• Z. Najafi, M. Mahdavi, M. Saeedi, E. Karimpour-Razkenari, N. Edraki, M. Sharifzadeh, M. Khanavi, and T. Akbarzadeh, “Novel Tacrine-Coumarin Hybrids Linked to 1,2,3-Triazole as Anti-Alzheimer’s Compounds: In Vitro and in Vivo Biological Evaluation and Docking Study,” Bioorganic Chemistry 83 (2019): 303–16. doi:10.1016/j.bioorg.2018.10.056
   PubMed Web of Science ®Google Scholar
• Q. He, J. Liu, J. S. Lan, J. Ding, Y. Sun, Y. Fang, N. Jiang, Z. Yang, L. Sun, Y. Jin, et al, “Coumarin-Dithiocarbamate Hybrids as Novel Multitarget AChE and MAO-B Inhibitors against Alzheimer’s Disease: Design, Synthesis and Biological Evaluation,” Bioorganic Chemistry 81 (2018): 512–28. doi:10.1016/j.bioorg.2018.09.010
   PubMed Web of Science ®Google Scholar
• A. Abdel-Aziem, B. S. Baaiu, A. W. Elbazzar, and F. Elabbar, “A Facile Synthesis of Some Novel Thiazoles, Arylazothiazoles, and Pyrazole Linked to Thiazolyl Coumarin as Antibacterial Agents,” Synthetic Communications. 50, no. 16 (2020): 2522–30. doi:10.1080/00397911.2020.1782431
   Web of Science ®Google Scholar
• A. Abdel-Aziem, B. S. Baaiu, and E. R. El-Sawy, “Reactions and Antibacterial Activity of 6-Bromo-3-(2-Bromoacetyl)-2H-Chromen-2-One,” Polycyclic Aromatic Compounds 42 (2021): 4809–18. doi:10.1080/10406638.2021.1916543
   Web of Science ®Google Scholar
• D. Feng, A. Zhang, Y. Yang, and P. Yang, “Coumarin-Containing Hybrids and Their Antibacterial Activities,” Archiv Der Pharmazie 353, no. 6 (2020): 1900380. doi:10.1002/ardp.201900380
   PubMed Web of Science ®Google Scholar
• C. Ranjan Sahoo, J. Sahoo, M. Mahapatra, D. Lenka, P. Kumar Sahu, B. Dehury, R. Nath Padhy, and S. Kumar Paidesetty, “Coumarin Derivatives as Promising Antibacterial Agent(s),” Arabian Journal of Chemistry 14, no. 2 (2021): 102922. doi:10.1016/j.arabjc.2020.102922
   Web of Science ®Google Scholar
• Y. F. Shen, L. Liu, C. Z. Feng, Y. Hu, C. Chen, G. X. Wang, and B. Zhu, “Synthesis and Antiviral Activity of a New Coumarin Derivative against Spring Viraemia of Carp Virus,” Fish & Shellfish Immunology 81 (2018): 57–66. doi:10.1016/J.FSI.2018.07.005
   PubMed Web of Science ®Google Scholar
• S. Mishra, A. Pandey, and S. Manvati, “Coumarin: An Emerging Antiviral Agent,” Heliyon 6, no. 1 (2020): e03217. doi:10.1016/j.heliyon.2020.e03217
   PubMed Web of Science ®Google Scholar
• N. Prahadeesh, M. Sithambaresan, and U. Mathiventhan, “A Study on Hydrogen Peroxide Scavenging Activity and Ferric Reducing Ability of Simple Coumarins,” Emerging Science Journal 2, no. 6 (2018): 417. doi:10.28991/esj-2018-01161
   Google Scholar
• M. Zhu, L. Ma, J. Wen, B. Dong, Y. Wang, Z. Wang, J. Zhou, G. Zhang, J. Wang, Y. Guo, et al, “Rational Design and Structure − Activity Relationship of Coumarin Derivatives Effective on HIV-1 Protease and Partially on HIV-1 Reverse Transcriptase,” European Journal of Medicinal Chemistry 186 (2020): 111900. doi:10.1016/j.ejmech.2019.111900
   PubMed Web of Science ®Google Scholar
• Z. Xu, Q. Chen, Y. Zhang, and C. Liang, “Coumarin-Based Derivatives with Potential anti-HIV Activity,” Fitoterapia 150 (2021): 104863. doi:10.1016/j.fitote.2021.104863
   PubMed Web of Science ®Google Scholar
• E. J. T. Sierra, C. F. Cordeiro, L. de Figueiredo Diniz, I. S. Caldas, J. A. Hawkes, and D. T. Carvalho, “Coumarins as Potential Antiprotozoal Agents: Biological Activities and Mechanism of Action,” Revista Brasileira de Farmacognosia 31, no. 5 (2021): 592–611. doi:10.1007/s43450-021-00169-y
   Google Scholar
• V. Mandlik, S. Patil, R. Bopanna, S. Basu, and S. Singh, “Biological Activity of Coumarin Derivatives as anti-Leishmanial Agents,” PLoS One 11, no. 10 (2016): e0164585. doi:10.1371/journal.pone.0164585
   PubMed Web of Science ®Google Scholar
• R. S. Keri, B. S. Sasidhar, B. M. Nagaraja, and M. A. Santos, “Recent Progress in the Drug Development of Coumarin Derivatives as Potent Antituberculosis Agents,” European Journal of Medicinal Chemistry 100 (2015): 257–69. doi:10.1016/j.ejmech.2015.06.017
   PubMed Web of Science ®Google Scholar
• S. M. Gomha, Y. H. Zaki, A. O. Abdelhamid, and R. A. Bunce, “Utility of 3-Acetyl-6-Bromo-2H-Chromen-2-One for the Synthesis of New Heterocycles as Potential Antiproliferative Agents,” Molecules (Basel, Switzerland) 20, no. 12 (2015): 21826–39. doi:10.3390/molecules201219803
   PubMed Web of Science ®Google Scholar
• R. H. Shoemaker, “The NCI60 Human Tumour Cell Line Anticancer Drug Screen,” Nature Reviews Cancer 6, no. 10 (2006): 813–23. doi:10.1038/nrc1951
   PubMed Web of Science ®Google Scholar
• M. R. Boyd, “The NCI in Vitro Anticancer Drug Discovery Screen,” Anticancer Drug Dev Guid. Published Online (Totowa, NJ: HumanaPress, 1997), 23–42. doi:10.1007/978-1-4615-8152-9_2
   Google Scholar
• M. R. Boyd, and K. D. Paull, “Some Practical Considerations and Applications of the National Cancer Institute in Vitro Anticancer Drug Discovery Screen,” Drug Development Research 34, no. 2 (1995): 91–109. doi:10.1002/ddr.430340203
   Web of Science ®Google Scholar