Molecular dynamics and computational study of Mannich-based coumarin derivatives: potent tyrosine kinase inhibitor

References

• Anary-Abbasinejad, M., Anaraki-Ardakani, H., & Hassanabadi, A. (2008). P2O5-hexamethyldisiloxane (HMDS): An efficient system to induce the three-component reaction of enolic systems, aromatic aldehydes, and acetonitrile. Synthetic Communications, 38(21), 3706–3716.
   Web of Science ®Google Scholar
• Arora, R. K., Kaur, N., Bansal, Y., & Bansal, G. (2014). Novel coumarin–benzimidazole derivatives as antioxidants and safer anti-inflammatory agents. Acta Pharmaceutica Sinica B, 4(5), 368–375.
   PubMed Web of Science ®Google Scholar
• Baral, N., Mohapatra, S., Raiguru, B. P., Mishra, N. P., Panda, P., Nayak, S., … Sahoo, C. R. (2019). Microwave‐assisted rapid and efficient synthesis of new series of chromene‐based 1, 2, 4‐oxadiazole derivatives and evaluation of antibacterial activity with molecular docking investigation. Journal of Heterocyclic Chemistry, 56(2), 552–565. doi:10.1002/jhet.3430
   Web of Science ®Google Scholar
• Chilin, A., Battistutta, R., Bortolato, A., Cozza, G., Zanatta, S., Poletto, G., … Pinna, L. A. (2008). Coumarin as attractive casein kinase 2 (CK2) inhibitor scaffold: An integrate approach to elucidate the putative binding motif and explain structure–activity relationships. Journal of Medicinal Chemistry, 51(4), 752–759. doi:10.1021/jm070909t
   PubMed Web of Science ®Google Scholar
• Cozzone, J. A. (2009). Bacterial tyrosine kinases: Novel targets for antibacterial therapy. Trends in Microbiology, 17(12), 536–543. doi:10.1016/j.tim.2009.09.005
   PubMed Web of Science ®Google Scholar
• Dehury, B., Behera, S. K., & Mahapatra, N. (2017). Structural dynamics of casein kinase I (CKI) from malarial parasite Plasmodium falciparum (Isolate 3D7): Insights from theoretical modelling and molecular simulations. Journal of Molecular Graphics and Modelling, 71, 154–166. doi:10.1016/j.jmgm.2016.11.012
   PubMed Web of Science ®Google Scholar
• Dehury, B., Patra, M. C., Maharana, J., Sahu, J., Sen, P., Modi, M. K., … Barooah, M. (2014). Structure-based computational study of two disease resistance gene homologues (Hm1 and Hm2) in maize (Zea mays L.) with implications in plant-pathogen interactions. PloS One, 9(5), e97852. doi:10.1371/journal.pone.0097852
   PubMed Web of Science ®Google Scholar
• Fang, C., Lee, K. K., Nietupski, R., Bates, R. H., Fernandez-Menendez, R., Lopez-Roman, E. M., … Fisher, S. (2018). Discovery of heterocyclic replacements for the coumarin core of anti-tubercular FadD32 inhibitors. Bioorganic & Medicinal Chemistry Letters, 28(22), 3529–3533. doi:10.1016/j.bmcl.2018.09.037
   PubMed Web of Science ®Google Scholar
• Girdhar, K., Dehury, B., Singh, M. K., Daniel, V. P., Choubey, A., Dogra, S., … Mondal, P. (2019). Novel insights into the dynamics behavior of glucagon-like peptide-1 receptor with its small molecule agonists. Journal of Biomolecular Structure and Dynamics, 37(15), 3976–3986. doi:10.1080/07391102.2018.1532818
   PubMed Web of Science ®Google Scholar
• Kontogiorgis, C. A., & Hadjipavlou-Litina, D. J. (2005). Synthesis and antiinflammatory activity of coumarin derivatives. Journal of Medicinal Chemistry, 48(20), 6400–6408. doi:10.1021/jm0580149
   PubMed Web of Science ®Google Scholar
• Kostova, I., Raleva, S., Genova, P., & Argirova, R. (2006). Structure-activity relationships of synthetic coumarins as HIV-1 inhibitors. Bioinorganic Chemistry and Applications, 2006, 1–9. doi:10.1155/BCA/2006/68274
   Web of Science ®Google Scholar
• Ladbury, J. E., Hensmann, M., Panayotou, G., & Campbell, I. D. (1996). Alternative modes of tyrosyl phosphopeptide binding to a Src family SH2 domain: Implications for regulation of tyrosine kinase activity. Biochemistry, 35 (34), 11062–11069. doi:10.1021/bi960543e
   PubMed Web of Science ®Google Scholar
• Lipinski, C. A., Lombardo, F., Dominy, B. W., & Feeney, P. J. (1997). Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Advanced Drug Delivery Reviews, 23(1–3), 3–25. doi:10.1016/S0169-409X(96)00423-1
   Web of Science ®Google Scholar
• Mah, S., Jang, J., Song, D., Shin, Y., Latif, M., Jung, Y., & Hong, S. (2019). Discovery of fluorescent 3-heteroarylcoumarin derivatives as novel inhibitors of anaplastic lymphoma kinase. Organic & Biomolecular Chemistry, 17(1), 186–194. doi:10.1039/C8OB02874E
   Web of Science ®Google Scholar
• Molinspiration. (2018). Molinspiration Cheminformatics. Nova ulica, Slovensky Grob, Slovak Republic. Retrieved from http://www.molinspiration.com/
   Google Scholar
• Mulhern, T. D., Shaw, G. L., Morton, C. J., Day, A. J., & Campbell, I. D. (1997). The SH2 domain from the tyrosine kinase Fyn in complex with a phosphotyrosyl peptide reveals insights into domain stability and binding specificity. Structure, 5(10), 1313–1323. doi:10.1016/S0969-2126(97)00283-9
   Google Scholar
• Roman, G. (2015). Mannich bases in medicinal chemistry and drug design. European Journal of Medicinal Chemistry, 89, 743–816. doi:10.1016/j.ejmech.2014.10.076
   PubMed Web of Science ®Google Scholar
• Rueping, M., Nachtsheim, B. J., & Sugiono, E. (2010). Direct catalytic benzylation of hydroxycoumarin-efficient synthesis of warfarin derivatives and analogues. Synlett, 2010(10), 1549–1553. doi:10.1055/s-0029-1219936
   Google Scholar
• Sahoo, C. R., Paidesetty, S. K., & Padhy, R. N. (2019). Norharmane as a potential chemical entity for development of anticancer drugs. European Journal of Medicinal Chemistry, 162, 752–764. doi:10.1016/j.ejmech.2018.11.024
   PubMed Web of Science ®Google Scholar
• Sahoo, J., & Sudhir Kumar, P. (2015). Biological evaluation of some 4-Hydroxy Coumarin analogues and their spectral characterization. Journal of Taibah University Medical Sciences, 10(3), 306–319. doi:10.1016/j.jtumed.2015.03.001
   Web of Science ®Google Scholar
• Sandhya, B., Giles, D., Mathew, V., Basavarajaswamy, G., & Abraham, R. (2011). Synthesis, pharmacological evaluation and docking studies of coumarin derivatives. European Journal of Medicinal Chemistry, 46(9), 4696–4701. doi:10.1016/j.ejmech.2011.07.013
   PubMedGoogle Scholar
• 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.
   PubMed Web of Science ®Google Scholar
• Swain, S. S., Paidesetty, S. K., Dehury, B., Sahoo, J., Vedithi, S. C., Mahapatra, N., … Padhy, R. N. (2018). Molecular docking and simulation study for synthesis of alternative dapsone derivative as a newer antileprosy drug in multidrug therapy. Journal of Cellular Biochemistry, 119(12), 9838–9852. doi:10.1002/jcb.27304
   PubMed Web of Science ®Google Scholar
• Tao, D., Wang, Y., Bao, X., Yang, B., Gao, F., Wang, L., … Li, L. (2019). Discovery of coumarin Mannich base derivatives as multifunctional agents against monoamine oxidase B and neuroinflammation for the treatment of Parkinson's disease. European Journal of Medicinal Chemistry, 173, 203–212. doi:10.1016/j.ejmech.2019.04.016
   PubMed Web of Science ®Google Scholar
• Zhang, L., & Xu, Z. (2019). Coumarin-containing hybrids and their anticancer activities. European Journal of Medicinal Chemistry, 181, 111587. doi:10.1016/j.ejmech.2019.111587
   PubMed Web of Science ®Google Scholar