Design, Synthesis, Crystal Structure, Biological Activity and Molecular Modeling of Novel Schiff Bases Derived from Chalcones and 5-Hydrazino-1,3-Dimethyl-4-Nitropyrazole as Anticancer Agents

References

• A. Kajal, S. Bala, S. Kamboj, N. Sharma, and V. Saini, “Schiff Bases: A Versatile Pharmacophore,” Journal of Catalysis 2013  (2013): 893512.
   Google Scholar
• H. M. Abosalim, M. A. Nael, and T. F. El-Moselhy, “Design, Synthesis and Molecular Docking of Chalcone Derivatives as Potential Anticancer Agents,” ChemistrySelect 6, no. 4 (2021): 888–895. doi:10.1002/slct.202004088
   Web of Science ®Google Scholar
• D. Gupta, and D. K. Jain, “Chalcone Derivatives as Potential Antifungal Agents: Synthesis, and Antifungal Activity,” Journal of Advanced Pharmaceutical Technology & Research 6, no. 3 (2015): 114–117. doi:10.4103/2231-4040.161507
   PubMed Web of Science ®Google Scholar
• E. N. Okolo, D. I. Ugwu, B. E. Ezema, J. C. Ndefo, F. U. Eze, C. G. Ezema, J. A. Ezugwu, and O. T. Ujam, “New Chalcone Derivatives as Potential Antimicrobial and Antioxidant Agent,” Scientific Reports 11, no. 1 (2021): 21781. doi:10.1038/s41598-021-01292-5
   PubMed Web of Science ®Google Scholar
• M. F. A. Mohamed, M. S. A. Shaykoon, M. H. Abdelrahman, B. E. M. Elsadek, A. S. Aboraia, and G. E. A. A. Abuo-Rahma, “Design, Synthesis, Docking Studies and Biological Evaluation of Novel Chalcone Derivatives as Potential Histone Deacetylase Inhibitors,” Bioorganic Chemistry 72 (2017): 32–41. doi:10.1016/j.bioorg.2017.03.005
   PubMed Web of Science ®Google Scholar
• K. Karrouchi, S. Radi, Y. Ramli, J. Taoufik, Y. N. Mabkhot, F. A. Al-Aizari, and M. Ansar. “Synthesis and Pharmacological Activities of Pyrazole Derivatives: A Review,” Molecules 23 (2018): 6-41. doi:10.3390/molecules23010134
   PubMed Web of Science ®Google Scholar
• A. Ansari, A. Ali, M. Asif, and S. Shamsuzzaman, “Review: Biologically Active Pyrazole Derivatives,” New Journal of Chemistry 41, no. 1 (2017): 16–41. doi:10.1039/C6NJ03181A
   Web of Science ®Google Scholar
• K. Dahlman-Wright, V. Cavailles, S. A. Fuqua, V. C. Jordan, J. A. Katzenellenbogen, K. S. Korach, A. Maggi, M. Muramatsu, M. G. Parker, and J.-A. Gustafsson, “International Union of Pharmacology. LXIV. Estrogen Receptors,” Pharmacological Reviews 58, no. 4 (2006): 773–781. doi:10.1124/pr.58.4.8
   PubMed Web of Science ®Google Scholar
• K. J. Hamilton, S. C. Hewitt, Y. Arao, and K. S. Korach, “Estrogen Hormone Biology,” Current Topics in Developmental Biology 125 (2017): 109–146. doi:10.1016/bs.ctdb.2016.12.005
   PubMed Web of Science ®Google Scholar
• H. Hua, H. Zhang, Q. Kong, and Y. Jiang, “Mechanisms for Estrogen Receptor Expression in Human Cancer,” Experimental Hematology & Oncology 7 (2018): 24. doi:10.1186/s40164-018-0116-7
   PubMed Web of Science ®Google Scholar
• F. Lumachi, D. A. Santeufemia, and S. M. Basso, “Current Medical Treatment of Estrogen Receptor-Positive Breast Cancer,” World Journal of Biological Chemistry 6, no. 3 (2015): 231–239. doi:10.4331/wjbc.v6.i3.231
   PubMedGoogle Scholar
• P. A. Halim, R. A. Hassan, K. O. Mohamed, S. O. Hassanin, M. G. Khalil, A. M. Abdou, and E. O. Osman, “Synthesis and Biological Evaluation of Halogenated Phenoxychalcones and Their Corresponding Pyrazolines as Cytotoxic Agents in Human Breast Cancer,” Journal of Enzyme Inhibition and Medicinal Chemistry 37, no. 1 (2022): 189–201. doi:10.1080/14756366.2021.1998023
   PubMed Web of Science ®Google Scholar
• K. A. Abu Safieh, A. M. Abu Mahthieh, M. M. El-Abadelah, M. T. Ayoub, and W. Voelter, “Synthesis of 5-Substituted 1,3-Dimethylpyrazolo[4,3-e][1,2,4]Triazines,” Monatshefte Für Chemie - Chemical Monthly 138, no. 2 (2007): 157–160. doi:10.1007/s00706-006-0583-0
   Google Scholar
• A. Abdel-Rahman, A. Abdel-Megied, M. Hawata, E. Kasem, and M. Shabaan, “Synthesis and Antimicrobial Evaluation of Some Chalcones and Their Derived Pyrazoles, Pyrazolines, Isoxazolines, and 5,6-Dihydropyrimidine-2-(1 H) -Thiones,” Monatshefte Für Chemie – Chemical Monthly 138, no. 9 (2007): 889–897. doi:10.1007/s00706-007-0700-8
   Google Scholar
• A. I. M. Ibrahim, H. Abul-Futouh, La. M. S. Bourghli, M. Abu-Sini, S. Sunoqrot, B. Ikhmais, V. Jha, Q. Sarayrah, D. H. Abulebdah, and W. H. Ismail, “Design and Synthesis of Thionated Levofloxacin: Insights into a New Generation of Quinolones with Potential Therapeutic and Analytical Applications,” Current Issues in Molecular Biology 44, no. 10 (2022): 4626–4638. doi:10.3390/cimb44100316
   PubMed Web of Science ®Google Scholar
• A. Waterhouse, M. Bertoni, S. Bienert, G. Studer, G. Tauriello, R. Gumienny, F. T. Heer, T. A. P. de Beer, C. Rempfer, L. Bordoli, et al. “SWISS-MODEL: Homology Modelling of Protein Structures and Complexes,” Nucleic Acids Research 46, NO. W1 (2018): W296–W303. doi:10.1093/nar/gky427
   PubMed Web of Science ®Google Scholar
• G. M. Morris, R. Huey, W. Lindstrom, M. F. Sanner, R. K. Belew, D. S. Goodsell, and A. J. Olson, “AutoDock4 and AutoDockTools4: Automated Docking with Selective Receptor Flexibility,” Journal of Computational Chemistry 30, no. 16 (2009): 2785–2791. doi:10.1002/jcc.21256
   PubMed Web of Science ®Google Scholar
• R. Dennington, and T. M. Keith. GaussView. (2009).
   Google Scholar
• M. Frisch, G. Trucks, H. Schlegel, G. Scuseria, M. Robb, J. Cheeseman, J. Montgomery, T. Vreven, K. Kudin, and J. Burant, Gaussian 03 (2004).
   Google Scholar
• J. J. P. Stewart, “Optimization of Parameters for Semiempirical Methods II. Applications,” Journal of Computational Chemistry 10, no. 2 (1989): 221–264. doi:10.1002/jcc.540100209
   Web of Science ®Google Scholar
• G. M. Morris, D. S. Goodsell, R. S. Halliday, R. Huey, W. E. Hart, R. K. Belew, and A. J. Olson, “Automated Docking Using a Lamarckian Genetic Algorithm and an Empirical Binding Free Energy Function,” Journal of Computational Chemistry 19, no. 14 (1998): 1639–1662. doi:10.1002/(SICI)1096-987X(19981115)19:14<1639::AID-JCC10>3.0.CO;2-B
   Web of Science ®Google Scholar
• E. F. Pettersen, T. D. Goddard, C. C. Huang, G. S. Couch, D. M. Greenblatt, E. C. Meng, and T. E. Ferrin, “UCSF Chimera—A Visualization System for Exploratory Research and Analysis,” Journal of Computational Chemistry 25, no. 13 (2004): 1605–1612. doi:10.1002/jcc.20084
   PubMed Web of Science ®Google Scholar
• M. Šudomová, S. T. S. Hassan, H. Khan, M. Rasekhian, and S. M. Nabavi, “A Multi-Biochemical and in Silico Study on anti-Enzymatic Actions of Pyroglutamic Acid against PDE-5, ACE, and Urease Using Various Analytical Techniques: Unexplored Pharmacological Properties and Cytotoxicity Evaluation,” Biomolecules 9 (2019): 392. doi:10.3390/biom9090392
   PubMed Web of Science ®Google Scholar
• A. Daina, O. Michielin, and V. Zoete, “iLOGP: A Simple, Robust, and Efficient Description of n-Octanol/Water Partition Coefficient for Drug Design Using the GB/SA Approach,” Journal of Chemical Information and Modeling 54, no. 12 (2014): 3284–3301. doi:10.1021/ci500467k
   PubMed Web of Science ®Google Scholar
• L. Hamadneh, B. Abu-Irmaileh, M. Al-Majawleh, Y. Bustanji, Y. Jarrar, and T. Al-Qirim, “Doxorubicin-Paclitaxel Sequential Treatment: Insights of DNA Methylation and Gene Expression Changes of Luminal a and Triple Negative Breast Cancer Cell Lines,” Molecular and Cellular Biochemistry 476, no. 10 (2021): 3647–3654. doi:10.1007/s11010-021-04191-5
   PubMed Web of Science ®Google Scholar
• S. Shukla, A. K. Sood, K. Goyal, A. Singh, V. Sharma, N. Guliya, S. Gulati, and S. Kumar, “Chalcone Scaffolds as Anticancer Drugs: A Review on Molecular Insight in Action of Mechanisms and Anticancer Properties,” Anti-Cancer Agents in Medicinal Chemistry 21, no. 13 (2021): 1650–1670. doi:10.2174/1871520620999201124212840
   PubMed Web of Science ®Google Scholar
• F. Gao, G. Huang, and J. Xiao, “Chalcone Hybrids as Potential Anticancer Agents: Current Development, Mechanism of Action, and Structure-Activity Relationship,” Medicinal Research Reviews 40, no. 5 (2020): 2049–2084. doi:10.1002/med.21698
   PubMed Web of Science ®Google Scholar
• A. Daina, O. Michielin, and V. Zoete, “SwissADME: A Free Web Tool to Evaluate Pharmacokinetics, Drug-Likeness and Medicinal Chemistry Friendliness of Small Molecules,” Scientific Reports 7 (2017): 42717. doi:10.1038/srep42717
   PubMed Web of Science ®Google Scholar
• D. F. Veber, S. R. Johnson, H.-Y. Cheng, B. R. Smith, K. W. Ward, and K. D. Kopple, “Molecular Properties That Influence the Oral Bioavailability of Drug Candidates,” Journal of Medicinal Chemistry 45, no. 12 (2002): 2615–2623. doi:10.1021/jm020017n
   PubMed Web of Science ®Google Scholar
• V. Ezhilarasan, O. P. Sharma, and A. Pan, “In Silico Identification of Potential Drug Targets in Clostridium difficile R20291: Modeling and Virtual Screening Analysis of a Candidate Enzyme MurG,” Medicinal Chemistry Research 22, no. 6 (2013): 2692–2705. doi:10.1007/s00044-012-0262-0
   Web of Science ®Google Scholar