Synthesis, Characterization and Molecular Docking of New Nucleosides and Schiff Bases Derived from Ampyrone as Antiviral Agents to Contain the COVID-19 Virus

References

• World Health Organization. “WHO Director-General’s Remarks at the media briefing on 2019-nCoV on 11 February 2020,” https://www.who.int/dg/speeches/detail/who-director-general-s-remarks-at-the-media-briefing-on-2019-ncov-on-11-february-2020 (accessed March 12, 2020). Geneva (Switzerland): World Health Organization, 2020.
   Google Scholar
• H. I. Hosein, M. D. Moore, and A. S. Abdel-Moneim, “Abdel-Moneim as: Known SARS-CoV-2 Infections: The Tip of an Important Iceberg,” The International Journal of Health Planning and Management 35, no. 5 (2020): 1270–3.
   PubMed Web of Science ®Google Scholar
• N. Zhu, D. Zhang, W. Wang, X. Li, B. Yang, J. Song, X. Zhao, B. Huang, W. Shi, R. Lu, et al., “A Novel Coronavirus from Patients with Pneumonia in China, 2019,” The New England Journal of Medicine 382, no. 8 (2020): 727–33.
   PubMed Web of Science ®Google Scholar
• J. Ziebuhr, E. J. Snijder, and A. E. Gorbalenya, “Virus-Encoded Proteinases and Proteolytic Processing in the Nidovirales,” The Journal of General Virology 81, no. Pt 4 (2000): 853–79.
   PubMed Web of Science ®Google Scholar
• X. Xu, Y. Liu, S. Weiss, E. Arnold, S. G. Sarafianos, and J. Ding, “Molecular Model of SARS Coronavirus Polymerase: Implications for Biochemical Functions and Drug Design,” Nucleic Acids Research 31, no. 24 (2003): 7117–30.
   PubMed Web of Science ®Google Scholar
• L. D. Eckerle, M. M. Becker, R. A. Halpin, K. Li, E. Venter, X. Lu, S. Scherbakova, R. L. Graham, R. S. Baric, T. B. Stockwell, et al., “Infidelity of SARS-CoV Nsp14-Exonuclease Mutant Virus Replication is Revealed by Complete Genome Sequencing,” PLoS Pathogens 6, no. 5 (2010): e1000896.
   PubMed Web of Science ®Google Scholar
• K. A. Ivanov, V. Thiel, J. C. Dobbe, Y. van der Meer, E. J. Snijder, and J. Ziebuhr, “Multiple Enzymatic Activities Associated with Severe Acute Respiratory Syndrome Coronavirus helicase,” Journal of virology 78, no. 11 (2004): 5619–32.
   PubMed Web of Science ®Google Scholar
• Y. Wang, X. Huang, T. Sun, G. Fan, Q. Zhan, and L. Weng, “Non‐HIV‐Infected Patients with Pneumocystis Pneumonia in the Intensive Care Unit: A Bicentric, Retrospective Study Focused on Predictive Factors of in‐Hospital Mortality,” The Clinical Respiratory Journal 16, no. 2 (2022): 152–61.. [CrossRef][10.1111/crj.13463]
   PubMed Web of Science ®Google Scholar
• A. V. Hebbani, S. Pulakuntla, P. Pannuru, S. Aramgam, K. R. Badri, and V. D. Reddy, “COVID-19: Comprehensive Review on Mutations and Current Vaccines,” Archives of Microbiology 204, no. 1 (2022): 1–17.
   Web of Science ®Google Scholar
• A. S. Abdel-Moneim, E. M. Abdelwhab, and Z. A. Memish, “Insights into SARS-CoV-2 Evolution, Potential Antivirals, and Vaccines,” Virology 558 (2021): 1–12.
   PubMed Web of Science ®Google Scholar
• S. H. Alotaibi and H. H. Amer, “Synthesis, Spectroscopic and Molecular Docking Studies on New Schiff Bases, Nucleosides and α-Aminophosphonate Derivatives as Antibacterial Agents,” Saudi Journal of Biological Sciences 27, no. 12 (2020): 3481–8.
   PubMed Web of Science ®Google Scholar
• S. N. Sriharsha, S. Satish, S. Shashikanth, and K. A. Raveesha, “Design, Synthesis and Antibacterial Activity of Novel1,3-Thiazolidine Pyrimidine Nucleoside Analogues ,” Bioorganic & Medicinal Chemistry 14, no. 22 (2006): 7476–81.
   PubMed Web of Science ®Google Scholar
• T. Al-Muamin, N. Al-Lami, S. Rahman, and R. Ali, “Synthesis, Characterization and Antimicrobial Activity of New Nucleoside Analogues from Benzotriazole,” Chemistry and Chemical Technology 10, no. 3: 271–78.
   Google Scholar
• L. E. Núñez, C. Méndez, A. F. Braña, G. Blanco, and J. A. Salas, “The Biosynthetic Gene Cluster for the Beta-lactam Carbapenem Thienamycin in Streptomyces cattleya ,” Chemistry & Biology 10, no. 4 (2003): 301–11.
   PubMedGoogle Scholar
• N. Watanabe, Y. Kabasawa, Y. Takase, M. Matsukura, K. Miyazaki, H. Ishihara, K. Kodama, and H. Adachi, “4-Benzylamino-1-Chloro-6-Substituted Phthalazines: Synthesis and Inhibitory Activity toward Phosphodiesterase 5,” Journal of Medicinal Chemistry 41, no. 18 (1998): 3367–72.
   PubMed Web of Science ®Google Scholar
• S. Demirayak, A. C. Karaburun, and R. Beis, “Some Pyrrole Substituted Aryl Pyridazinone and Phthalazinone Derivatives and Their Antihypertensive Activities,” European Journal of Medicinal Chemistry 39, no. 12 (2004): 1089–95.
   PubMed Web of Science ®Google Scholar
• E. Lenz, I. Wilson, B. Wright, E. Partridge, C. Rodgers, P. Haycock, J. Lindon, and J. Nicholson, “A Comparison of Quantitative NMR and Radiolabelling Studies of the Metabolism and Excretion of Statil™(3-(4-Bromo-2-Fluorobenzyl)-4-Oxo-3H-Phthalazin-1-Ylacetic Acid) in the Rat,” Journal of Pharmaceutical and Biomedical Analysis 28, no. 1 (2002): 31–43.
   PubMed Web of Science ®Google Scholar
• D. S. Dogruer, E. Kupeli, E. Yesilada, and M. F. Sahin, “Synthesis of New 2-[1(2H)-phthalazinon-2-yl]acetamide and 3-[1(2H)-phthalazinon-2-yl]propanamide Derivatives as Antinociceptive and Anti-inflammatory Agents ,” Archiv Der Pharmazie 337, no. 6 (2004): 303–10.
   PubMed Web of Science ®Google Scholar
• M. K. Mishra, A. K. Gupta, S. Negi, and M. Bhatt, “Synthesis of Some New Oxadiazole with Antimicrobial Activity,” International Journal of Pharmaceutical Sciences and Research 1 (2010): 172–7.
   Google Scholar
• R. Ramajayam, K. P. Tan, H. G. Liu, and P. H. Liang, “Synthesis, Docking Studies, and Evaluation of Pyrimidines as Inhibitors of SARS-CoV 3CL Protease,” Bioorganic & Medicinal Chemistry Letters 20, no. 12 (2010): 3569–72.
   PubMed Web of Science ®Google Scholar
• M. Zhu, L. Ma, H. Zhou, B. Dong, Y. Wang, Z. Wang, J. Zhou, G. Zhang, J. Wang, C. Liang, et al., “Preliminary SAR and Biological Evaluation of Potent HIV-1 Protease Inhibitors with Pyrimidine Bases as Novel P2 Ligands to Enhance Activity against DRV-Resistant HIV-1 Variants,” European Journal of Medicinal Chemistry 185 (2020): 111866.
   PubMed Web of Science ®Google Scholar
• M. A. Hosny, Y. H. Zaki, W. A. Mokbel, and A. O. Abdelhamid, “Synthesis, Characterization, Antimicrobial Activity and Anticancer of Some New Pyrazolo [1, 5-a] Pyrimidines and Pyrazolo [5, 1-c] 1, 2, 4-Triazines,” Medicinal Chemistry 16, no. 6 (2020): 750–60.
   PubMed Web of Science ®Google Scholar
• Y. H. Zaki, M. S. Al-Gendey, and A. O. Abdelhamid, “A Facile Synthesis, and Antimicrobial and Anticancer Activities of Some Pyridines, Thioamides, Thiazole, Urea, Quinazoline, β-Naphthyl Carbamate, and Pyrano [2, 3-d] Thiazole Derivatives,” Chemistry Central Journal 12, no. 1 (2018): 1–14.
   PubMedGoogle Scholar
• Y. H. Zaki, S. M. Gomha, and A. M. G. Mohamed, “Utility of 2-Thioxo-Pyrido [2, 3-d] Pyrimidinone in Synthesis of Pyridopyrimido [2, 1-b][1, 3, 5]-Thiadiazinones and Pyridopyrimido [2, 1-b][1, 3] Thiazinones as Antimicrobial Agents,” Chemistry Central Journal 11, no. 1 (2017): 1–10.
   PubMedGoogle Scholar
• S. M. Gomha, Y. H. Zaki, and A. O. Abdelhamid, “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.
   PubMed Web of Science ®Google Scholar
• A. O. Abdelhamid, E. K. A. Abdelall, and Y. H. Zaki, “Reactions with Hydrazonoyl Halides 62: Synthesis and Antimicrobial Evaluation of Some New Imidazo [1, 2‐a] Pyrimidine, Imidazo [1, 2‐a] Pyridine, Imdazo [1, 2‐b] Pyrazole, and Quinoxaline Derivatives,” Journal of Heterocyclic Chemistry 47, no. 2 (2010): 482.
   Web of Science ®Google Scholar
• A. O. Abdelhamid, M. A. Mohamed, and Y. H. Zaki, “Reactions with Hydrazonoyl Halides 59: Synthesis and Antimicrobial Activity of 2, 3-Dihydro-1, 3, 4-Thiadiazole, Triazolino [4, 3-a] Pyrimidine, and Pyrimido [1, 2-b][1, 2, 4, 5] Tetrazin-6-One Containing Benzofuran Moiety,” Phosphorus, Sulfur, and Silicon and the Related Elements 183, no. 7 (2008): 1746–54.
   Web of Science ®Google Scholar
• H. H. Amer, S. H. Alotaibi, A. H. Trawneh, A. M. Metwaly, and I. H. Eissa, “Anticancer Activity, Spectroscopic and Molecular Docking of Some New Synthesized Sugar Hydrazones, Arylidene and α-Aminophosphonate Derivatives,” Arabian Journal of Chemistry 14, no. 10 (2021): 103348.
   Web of Science ®Google Scholar
• A. Aboelmagd, S. H. Alotaibi, S. M. El Rayes, G. M. Elsayed, I. A. I. Ali, W. Fathalla, F. H. Pottoo, and F. A. Khan, “Synthesis and Anti Proliferative Activity of New N‐Pentylquinoxaline Carboxamides and Their O‐Regioisomer,” ChemistrySelect 5, no. 43 (2020): 13439–53.
   Web of Science ®Google Scholar
• A. O. Abdelhamid, A. R. Sayed, and Y. H. Zaki, “Reaction of Hydrazonoyl Halides 511: A Facile Synthesis of 5-Arylthiazoles and Triazolino [4, 3-a] Pyrimidines as Antimicrobial Agents,” Phosphorus, Sulfur, and Silicon and the Related Elements 182, no. 7 (2007): 1447–57.
   Web of Science ®Google Scholar
• J. L. Sussman, D. Lin, J. Jiang, N. O. Manning, J. Prilusky, O. Ritter, and E. E. Abola, “Protein Data Bank (PDB): Database of Three-Dimensional Structural Information of Biological Macromolecules,” Acta Crystallographica. Section D, Biological Crystallography 54, no. Pt 6, Pt 1 (1998): 1078–84.
   PubMedGoogle Scholar
• L. J. Reed and H. Muench, “A Simple Method of Estimating Fifty per Cent Endpoints,” American Journal of Epidemiology 27, no. 3 (1938): 493–7.
   Google Scholar
• A. Rfaki, N. Touil, M. Hemlali, S. Alaoui Amine, M. Melloul, M. A. El Alaoui, H. Elannaz, A. I. Lahlou, M. Elouennass, K. Ennibi, et al., “Complete Genome Sequence of a SARS-CoV-2 Strain Sampled in Morocco in May 2020, Obtained Using Sanger Sequencing,” Microbiology Resource Announcements 10, no. 20 (2021): e00387–00321..
   PubMed Web of Science ®Google Scholar
• M. Y. Gokhale, W. R. Kearney, and L. E. Kirsch, “Glycosylation of Aromatic Amines I: Characterization of Reaction Products and Kinetic Scheme,” AAPS PharmSciTech 10, no. 2 (2009): 317–28.
   PubMed Web of Science ®Google Scholar
• R. R. Deshpande, A. P. Tiwari, N. Nyayanit, and M. Modak, “In Silico Molecular Docking Analysis for Repurposing Therapeutics against Multiple Proteins from SARS-CoV-2,” European Journal of Pharmacology 886 (2020): 173430.
   PubMed Web of Science ®Google Scholar
• M. A. Abu-Zaied, G. H. Elgemeie, and N. M. Mahmoud, “Anti-Covid-19 Drug Analogues: synthesis of Novel Pyrimidine Thioglycosides as Antiviral Agents against SARS-COV-2 and Avian Influenza H5N1 Viruses,” ACS Omega 6, no. 26 (2021): 16890–904.
   PubMed Web of Science ®Google Scholar