Novel synthesis of a new class of substituted S-glycosylisothiourea derivatives and their conversion to 5-amino-1,2,4-triazoles

References

• Larsen, P. K.; Liljefors, T.; Madsen, H. Text Book of Drug Design and Discovery, 3rd ed.; Taylor and Francis: London, New York, 2002; Vol. 511.
   Google Scholar
• Compañón, I.; Guerreiro, A.; Mangini, V.; Castro-López, J.; Escudero-Casao, M.; Avenoza, A.; Busto, J. H.; Castillón, S.; Jiménez-Barbero, J.; Asensio, J. L.; et al. Structure-Based Design of Potent Tumor-Associated Antigens: Modulation of Peptide Presentation by Single-Atom O/S or O/Se Substitutions at the Glycosidic Linkage. J. Am. Chem. Soc. 2019, 141, 4063–4072. DOI: 10.1021/jacs.8b13503.
   PubMed Web of Science ®Google Scholar
• Komor, R.; Pastuch-Gawołek, G.; Sobania, A.; Jadwinski, M.; Szeja, W. Application of Different Alpha-1-Thioglycosides Preparation Methods in Synthesis of 5-Nitro-2-Pyridyl-1- Thioglycosides Substrates in Synthesis of Conjugates with Uridine Moiety. Part I. Acta Pol. Pharm. 2012, 69, 1259–1269.
   PubMed Web of Science ®Google Scholar
• Abu-Zaied, M. A.; El-Telbani, E. M.; Elgemeie, G. H.; Nawwar, G. A. Synthesis and In Vitro Anti-Tumor Activity of New Oxadiazole Thioglycosides. Eur. J. Med. Chem. 2011, 46, 229–235. DOI: 10.1016/j.ejmech.2010.11.008.
   PubMed Web of Science ®Google Scholar
• Elgemeie, G. H.; Salah, A. M.; Abbas, N. S.; Hussein, H. A.; Mohamed, R. A. Nucleic Acid Components and Their Analogs: Design and Synthesis of Novel Cytosine Thioglycoside Analogs. Nucleosides Nucleotides Nucleic Acids 2017, 36, 139–150. DOI: 10.1080/15257770.2016.1231318.
   PubMed Web of Science ®Google Scholar
• Elgemeie, G. H.; Ahmed, M. M. A New Class of Biheterocyclic Thioglycosides from Pyridine-2(1H) Thiones. Nucleosides Nucleotides Nucleic Acids. 2002, 21, 837–847. DOI: 10.1081/NCN-120016511.
   PubMed Web of Science ®Google Scholar
• Elgemeie, G. H.; Attia, A. M.; Al-Kabai, S. S. Nucleic Acid Components and Their Analogues: New Synthesis of Bicyclic Thiopyrimidine Nucleosides. Nucleosides Nucleotides Nucleic Acids 2000, 19, 723–733. DOI: 10.1080/15257770008035020.
   PubMed Web of Science ®Google Scholar
• Elgemeie, G. H.; Heikel, A. Z.; Ahmed, M. A. A Direct Route to 2-(β-D-Ribofuranosylthio) Pyridine Glycosides. Nucleosides Nucleotides 2002, 21, 411–416. DOI: 10.1081/NCN-120014813.
   Google Scholar
• Elgemeie, G. H.; Fathy, N. M.; Farag, A. B.; Al-Kursani, S. S. Antimetabolites: Design, Synthesis, and Cytotoxic Evaluation of Novel Dihydropyridine Thioglycosides and Pyridine Thioglycosides. Nucleosides Nucleotides Nucleic Acids. 2017, 36, 355–377. DOI: 10.1080/15257770.2017.1297454.
   PubMed Web of Science ®Google Scholar
• Zhang, G. L.; Gadi, M. R.; Cui, X.; Liu, D.; Zhang, J.; Saikam, V.; Gibbons, C.; Wang, P. G.; Li, L. Protecting-Group-Free S-Glycosylation towards Thioglycosides and Thioglycopeptides in Water. Green Chem. 2021, 23, 2907–2912. DOI: 10.1039/D1GC00098E.
   PubMed Web of Science ®Google Scholar
• Wen, P.; Větvička, V.; Crich, D. Synthesis and Evaluation of Oligomeric Thioether-Linked Carbacyclic β-(1?3)-Glucan Mimetics. J. Org. Chem. 2019, 84, 5554–5563. DOI: 10.1021/acs.joc.9b00504.
   PubMed Web of Science ®Google Scholar
• Scott, K. A.; Njardarson, J. T. Analysis of US FDA-Approved Drugs Containing Sulfur Atoms. Top. Curr. Chem. (Cham.). 2018, 376, 5. DOI: 10.1007/s41061-018-0184-5.
   PubMed Web of Science ®Google Scholar
• Ryzhakov, D.; Beillard, A.; Le Bideau, F.; Ahmed Atto Al-Shuaeeb, R.; Alami, X.; Bantreil, M.; Bonnemoy, A.; Gautier, A.; Lamaty, F.; Messaoudi, S. Azoliums and g(I)-N-Heterocyclic Carbene Thioglycosides: Synthesis, Reactivity and Bioactivity. Eur. J. Org. Chem. 2022, 2022, 49–56. DOI: 10.1002/ejoc.202101499.
   Web of Science ®Google Scholar
• Elgemeie, G. H.; Kamal, E. A. Pyrimidinethione Nucleosides and Their Deaza Analogues. Nucleosides Nucleotides Nucleic Acids 2002, 21, 287–325. DOI: 10.1081/NCN-120006827.
   PubMed Web of Science ®Google Scholar
• Azzam, R. A.; Gad, N. M.; Elgemeie, G. H. Novel Thiophene Thioglycosides Substituted with the Benzothiazole Moiety: Synthesis, Characterization, Antiviral and Anticancer Evaluations, and NS3/4A and USP7 Enzyme Inhibitions. ACS Omega 2022, 7, 35656–35667. DOI: 10.1021/acsomega.2c03444.
   PubMed Web of Science ®Google Scholar
• Azzam, R. A.; Elgemeie, G. H.; Gad, N. M.; Jones, P. G. Crystal Structure of 4-Amino-5-(4-Bromobenzoyl)-3-(Benzo[d]Thiazol-2-yl)-2-[(2',3',4',6'-tetra-O-Acetyl-β-D-Galactopyranosyl)Sulfanyl]Thiophene. IUCrdata. 2022, 7, x220412. DOI: 10.1107/S2414314622004126.
   PubMedGoogle Scholar
• Elgemeie, G. H.; Alkhursani, S. A.; Mohamed, R. A. New Synthetic Strategies for Acyclic and Cyclic Pyrimidinethione Nucleosides and Their Analogues. Nucleosides Nucleotides Nucleic Acids 2019, 38, 12–87. DOI: 10.1080/15257770.2018.1498511.
   PubMed Web of Science ®Google Scholar
• Elgemeie, G. H.; Abu-Zaied, M. A.; Loutfy, S. A. 4-Aminoantipyrine in Carbohydrate Research: Design, Synthesis and Anticancer Activity of a Novel Class of Derivatives of 4-Aminoantipyrine Thioglycosides and Their Corresponding Pyrazolopyrimidine and Pyrazolopyridine Thioglycosides. Tetrahedron 2017, 73, 5853–5861. DOI: 10.1016/j.tet.2017.08.024.
   Web of Science ®Google Scholar
• Scala, S.; Akhmed, N.; Rao, U. S.; Paul, K.; Lan, L.; Dickstein, B.; Lee, J.; Elgemeie, G. H.; Stein, W. D.; Bates, S. E. P-Glycoprotein Substrates and Antagonists Cluster into Two Distinct Groups. Mol. Pharmacol. 1997, 51, 1024–1033. DOI: 10.1124/mol.51.6.1024.
   PubMed Web of Science ®Google Scholar
• Elgemeie, G. H.; Mahdy, E. M.; Elgawish, M. A.; Ahmed, M. M.; Shousha, W. G.; Eldin, M. E. A New Class of Antimetabolites: Pyridine Thioglycosides as Potential Anticancer Agents. Z Naturforsch. C J. Biosci. 2010, 65, 577–587. DOI: 10.1515/znc-2010-9-1008.
   PubMed Web of Science ®Google Scholar
• Elgemeie, G. H.; Zaghary, W. A.; Amin, K. M.; Nasr, T. M. First Synthesis of Thiophene Thioglycosides. J. Carbohydr. Chem. 2009, 28, 161–178. DOI: 10.1080/07328300902789209.
   Web of Science ®Google Scholar
• Abu-Zaied, M. A.; Elgemeie, G. H. Synthesis of the First Novel Pyrazole Thioglycosides as Deaza Ribavirin Analogues. Nucleosides Nucleotides Nucleic Acids 2017, 36, 713–725. DOI: 10.1080/15257770.2017.1378817.
   PubMed Web of Science ®Google Scholar
• Abu-Zaied, M. A.; Hebishy, A. M. S.; Elgemeie, G. H.; Salama, H. T.; Jones, P. G. Crystal Structure of 5-(β-D-Glucopyranosylthio)-N-(4-Methylphenyl)-1,3,4-Thiadiazol-2-Amine. Acta Cryst. 2023, E79, 652–656. DOI: 10.1107/S2056989023005248.
   Google Scholar
• Elgemeie, G. H.; Abu-Zaied, M. A.; Nawwar, G. A. First Novel Synthesis of Triazole Thioglycosides as Ribavirin Analogues. Nucleosides Nucleotides Nucleic Acids 2018, 37, 112–123. DOI: 10.1080/15257770.2017.1423079.
   PubMed Web of Science ®Google Scholar
• Elgemeie, G. H.; Farag, A. B.; Amin, K. M.; El-Badry, O. M.; Hassan, G. S. Design, Synthesis and Cytotoxic Evaluation of Novel Heterocyclic Thioglycosides. Med. Chem. 2014, 4, 814–820. DOI: 10.4172/2161-0444.1000234.
   Google Scholar
• Abu-Zaied, M. A.; Elgemeie, G. H. Thiazoles in Glycosylation Reactions: Novel Synthesis of Thiazole Thioglycosides. Heteroatom Chem. 2017, 28, e21404. DOI: 10.1002/hc.21404.
   Web of Science ®Google Scholar
• Elgemeie, G. H.; El-Enany, M. M.; Ismail, M. M.; Ahmed, E. K. Nucleic Acid Components and Their Analogues: A Novel and Efficient Method for the Synthesis of a New Class of Bipyridyl and Biheterocyclic-Nitrogen Thioglycosides from Pyridine-2(1H)-Thiones. Nucleosides Nucleotides Nucleic Acids 2002, 21, 477–493. DOI: 10.1081/NCN-120014820.
   PubMed Web of Science ®Google Scholar
• Elgemeie, G. H.; Fathy, N. M.; Farag, A. B.; Bin Yahab, A. M. Design and Synthesis of a New Class of Indeno[1,2-b]Pyridine Thioglycosides. Nucleosides Nucleotides Nucleic Acids 2020, 39, 1134–1149. DOI: 10.1080/15257770.2020.1780436.
   PubMed Web of Science ®Google Scholar
• Elgemeie, G. H.; Zaghary, W. A.; Amin, K. M.; Nasr, T. M. First Synthesis of Thienopyrazole Thioglycosides. J. Carbohydr. Chem. 2008, 27, 345–356. DOI: 10.1080/07328300802236178.
   Web of Science ®Google Scholar
• Abu-Zaied, M. A.; Elgemeie, G. H. A Facile Synthesis of Novel Pyrazolopyrimidine Thioglycosides as Purine Thioglycoside Analogues. Nucleosides Nucleotides Nucleic Acids 2018, 37, 67–77. DOI: 10.1080/15257770.2017.1419254.
   PubMed Web of Science ®Google Scholar
• Elgemeie, G.; Abou-Zeid, M.; Alsaid, S.; Hebishy, A.; Essa, H. Novel Nucleoside Analogues: First Synthesis of Pyridine-4-Thioglycosides and Their Cytotoxic Evaluation. Nucleosides Nucleotides Nucleic Acids 2015, 34, 659–673. DOI: 10.1080/15257770.2015.1071843.
   PubMed Web of Science ®Google Scholar
• Abu-Zaied, M. A.; Mahmoud, N. M.; Elgemeie, G. H. Toward Developing Therapies against Corona Virus: Synthesis and Anti-Avian Influenza Virus Activity of Novel Cytosine Thioglycoside Analogues. ACS Omega 2020, 5, 20042–20050. DOI: 10.1021/acsomega.0c01537.
   PubMed Web of Science ®Google Scholar
• Abu-Zaied, M. A.; Mahmoud, N. M.; Elgemeie, G. H. Synthesis of Novel Pyrimidine Thioglycosides as Structural Analogs of Favipiravir (Avigan) and Their Antibird Flu Virus Activity. Nucleosides Nucleotides Nucleic Acids 2021, 40, 336–356. DOI: 10.1080/15257770.2021.1872794.
   PubMed Web of Science ®Google Scholar
• Elgemeie, G.; Abu-Zaied, M.; Azzam, R. Antimetabolites: A First Synthesis of a New Class of Cytosine Thioglycoside Analogs. Nucleosides Nucleotides Nucleic Acids 2016, 35, 211–222. DOI: 10.1080/15257770.2015.1127961.
   PubMed Web of Science ®Google Scholar
• Abu-Zaied, M. A.; Hammad, S. F.; Halaweish, F. T.; Elgemeie, G. H. Sofosbuvir Thio-Analogues: Synthesis and Antiviral Evaluation Ofthe First Novel Pyridine- and Pyrimidine-Based Thioglycoside Phosphoramidates. ACS Omega 2020, 5, 14645–14655. DOI: 10.1021/acsomega.0c01364.
   PubMed Web of Science ®Google Scholar
• Abu-Zaied, M. A.; Elgemeie, G. H.; Halaweish, F. T.; Hammad, S. F. Synthesis of Novel Pyridine and Pyrimidine Thioglycoside Phosphoramidates for the Treatment of COVID-19 and Influenza a Viruses. Nucleosides Nucleotides Nucleic Acids 2022, 41, 851–877. DOI: 10.1080/15257770.2022.2085293.
   PubMed Web of Science ®Google Scholar
• Elgemeie, G. H.; Fathy, N.; Zaghary, W.; Farag, A. S-Glycosides in Medicinal Chemistry: Novel Synthesis of Cyanoethylene Thioglycosides and Their Pyrazole Derivatives. Nucleosides Nucleotides Nucleic Acids 2017, 36, 198–212. DOI: 10.1080/15257770.2016.1257807.
   PubMed Web of Science ®Google Scholar
• Elgemeie, G. H.; Elsayed, S. H.; Hassan, A. S. Direct Route to a New Class of Acrylamide Thioglycosides and Their Conversions to Pyrazole Derivatives. Synth. Commun. 2008, 38, 2700–2706. DOI: 10.1080/00397910802222605.
   Web of Science ®Google Scholar
• Elgemeie, G. H.; Fathy, N. M.; Farag, A. B.; El-Badry, O. M.; Hassan, G. S.; Amin, K. M.; Halaweish, F. Design, Synthesis and In Vitro Anti-Tumor Evaluation of Novel Acrylohydrazide Thioglycosides. Med. Chem. 2014, 4, 400–406. DOI: 10.4172/2161-0444.1000171.
   Google Scholar
• Elgemeie, G. H.; Saber, N. M. Synthesis and In Vitro Anti-Tumor Activity of a New Class of Acyclic Thioglycosides. Nucleosides Nucleotides Nucleic Acids 2015, 34, 463–474. DOI: 10.1080/15257770.2015.1016168.
   PubMed Web of Science ®Google Scholar
• Abu-Zaied, M. A.; Elgemeie, G. H.; Jones, P. G. Crystal Structure of 4,6-Dimethyl2-[(2,3,4,6-tetra-O-Acetyl-β-D-Galactopyranosyl) Sulfanyl] Pyrimidine. Acta Cryst. 2019, E75, 1820–1823. DOI: 10.1107/S205698901901449X.
   Google Scholar
• Hammad, S. F.; Masoud, D. M.; Elgemeie, G. H.; Jones, P. G. Crystal Structure of Racemic 2-[(β-Arabinopyranosyl)Sulfanyl]-4,6-Diphenylpyridine-3-Carbonitrile. Acta Cryst. 2018, E74, 853–856. DOI: 10.1107/S2056989018007284.
   Google Scholar
• Kalinina, S. A.; Kalinina, D. V.; Dolzhenko, A. V. A One-Pot, Three-Component, Microwave-Promoted Synthesis of 2-Amino-Substituted 7-Amino-1,2,4-Triazolo[1,5-a][1,3,5]Triazines. Tet. Lett. 2013, 54, 5537–5540. DOI: 10.1002/chin.201403197.
   Web of Science ®Google Scholar
• Scott, A. C.; et al. Laboratory Control of Antimicrobial Therapy. In Practical Medical Microbiology, 13th ed.; Collee, J. G., Duguid, J. P., Fraser, A. G., Marmion, B. P., Eds.; Churchill Livingstone: Edinburgh, 1989; p. 161–181.
   Google Scholar