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Original Articles

Design, synthesis, and in vitro anti-hepatocellular carcinoma of novel thymine thioglycoside analogs as new antimetabolic agents

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Pages 328-342 | Received 19 Feb 2016, Accepted 05 Jan 2017, Published online: 31 Mar 2017

References

  • Jordheim, L.P.; Durantel, D.; Zoulim, F.; Dumontet, C. Advances in the development of nucleoside and nucleotide analogues for cancer and viral diseases. Nat. Rev. Drug Discov. 2013, 12, 447–464.
  • 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, 229–238.
  • Elgemeie, G.H.; Jones, P.G. 2-(2′,3′,4′,6′-Tetra-O-acetyl-β-D-glucopyranosylthio)-4-pyridin-4-yl 6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-3-carbonitrile. Acta Cryst. 2002, E58, 1244–1245.
  • Elgemeie, G.H.; Zaghary, W.A.; Amin, K.M.; Nasr, T.M. First synthesis of thienopyrazole thioglycosides. J. Carbohydrate Chem. 2008, 27, 345–356.
  • Elgemeie, G.H.; Zaghary, W.A.; Amin, K.M.; Nasr, T.M. First synthesis of thiophene thioglycosides. J. Carbohydrate Chem. 2009, 28, 161–178.
  • 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. (Omics) 2014, 4, 814–820.
  • Elgemeie, G.H.; Saber, N.M. Synthesis and in vitro anti-tumor activity of a new class of acyclic thioglycosides. Nucleos. Nucleot. Nucleic Acids 2015, 34, 463–477.
  • Elgemeie, G.H.; Hussein, M.M.; Al-Khursani, S.A. A total synthesis of a new class of biazine thioglycosides. J. Carbohydrate Chem. 2004, 23, 465–481.
  • Elgemeie, G.H.; Attia, A. A new class of dihydropyridine thioglycosides via piperdinium salts. Synth. Commun. 2003, 33, 2243–2267.
  • Scala, S.; Akhmed, N.; Rao, U. S.; Paull, 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.
  • 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. 2010, 65, 577–587.
  • Still, I.W.; Plavac, N.; Mackinnon, T.M.; Chauhan, M.S. Carbon-13 nuclear magnetic resonance spectra of organic sulfur compounds. Comparison of chemical shifts for carbonyl and thiocarbonyl compounds in the pyron, thiopyrone, and pyridone series. Can. J. Chem. 1976, 54, 280–289.
  • Stefaniak, L. Nitrogen-14 and carbon-13 NMR of tautomeric systems of mercapto- and amino-pyridines. Org. Magn. Reson. 1979, 12, 379–385.
  • Mosmann, T. Rapid colorimetric assay for cellular growth and survival: Application to proliferation and cytotoxicity assays. J. Immunol. Methods 1983, 65, 55–63.
  • Kumar, V.P.; Cisneros, J.A.; Frey, K.M.; Castellanos-Gonzalez, A.; Wang, Y.; Gangjee, A.; White, A.C.; Jorgensen, W.L.; Anderson, K.S. Structural studies provide clues for analog design of specific inhibitors of Cryptosporidium hominis thymidylate synthase-dihydrofolate reductase. Bioorg. Med. Chem. Lett. 2014, 24, 4158–61.
  • Molecular Operating Environment (MOE), 2013.08, Chemical Computing Group Inc., 1010 Sherbooke St. West, Suite #910, Montreal, QC, Canada 2013, H3A, 2R7.
  • Labute, P. Assignment of ionization states and hydrogen coordinates to macromolecular structures. Proteins 2008, 75, 187–205.
  • Naïm, M.; Bhat, S.; Rankin, K.N.; Dennis, S.; Chowdhury, S.F.; Siddiqi, I.; Drabik, P.; Sulea, T.; Bayly, C.I.; Jakalian, A.; Purisima, E.O. Solvated interaction energy (SIE) for scoring protein-ligand binding affinities. 1. Exploring the parameter space. J. Chem. Inf. Model 2007, 47, 122–133.

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