234
Views
33
CrossRef citations to date
0
Altmetric
Original Articles

Novel Nucleoside Analogues: First Synthesis of Pyridine-4-Thioglycosides and Their Cytotoxic Evaluation

, , , &
Pages 659-673 | Received 01 Aug 2014, Accepted 27 Jun 2015, Published online: 13 Oct 2015

REFERENCES

  • Bozo, E.; Demeter, A.; Rilla, A.; Kuszmann, J. The behavior of two thiosugar thioglycosides towards oxidation. Tetrahedron: Asymmetry 2001, 3423–3433.
  • Despras, G.; Robert, R.; Sendid, B.; Machez, E.; Poulain, D.; Mallet, J. Biotin sulfone tagged oligomannosides as immunogens for eliciting antibodies against specific mannan epitopes. Bioorg. Med. Chem. 2012, 20, 1817–1831.
  • Suzuki, K.; Ito, Y.; Kanie, O. An improved method for the synthesis of protected glycosyl fluorides from thioglycosides using N,N diethylaminosulfur trifluoride (DAST). Carbohydr. Res. 2012, 359, 81–91.
  • Komor, R.; Kasprzycka, A.; Gawołek, G.; Szeja, W. Simple synthesis of glycosylthiols and thioglycosides by rearrangement of O-glycosyl thionocarbamates. Carbohydr. Res. 2014, 396, 37–42.
  • 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.
  • Elgemeie, G.H.; Elsayed, S.H.; Hassan, A.S. Design and synthesis of the first thiophene thioglycosides. Synth. Commun. 2009, 39, 1781–1792.
  • Elgemeie, G.H.; Zaghary, W.A.; Amin, K.M.; Nasr, T.M. First synthesis of thiophene thioglycosides. J. Carbohydr. Chem. 2009, 28, 161–172.
  • Elgemeie, G.H.; Eltamny, E.H.; Elgawad, I.I.; Mahmoud, N.M. Direct route to novel 2-(β-D-xylo- and arabinopyranosylthio)dihydropyridine glycosides and their corresponding dehydrogenated forms. Synth. Commun. 2009, 39, 443–458.
  • Elgemeie, G.H.; Hussein, M.M.; 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.; Attia, A.M.; Hussain, B.A. A synthetic strategy to a new class of cycloalkane ring-fused pyridine nucleosides as potential anti-HIV agents. Nucleos. Nucleot. 1998, 17, 855–868.
  • Elgemeie, G.H.; Mansour, O.A.; Metwally, N.H. Synthesis and anti-HIV activity of different novel nonclassical nucleosides. Nucleos. Nucleot. 1999, 18, 113–123.
  • Elgemeie, G.H.; Zaghary, W.A.; Amin, K.M.; Nasr, T.M. First synthesis of thienopyrazole thioglycosides. J. Carbohydr. Chem. 2008, 27, 345–355.
  • Jandu, K.S.; Selwood, D.L. 4’-Thio-nucleosides via in situ pyranose-furanose rearrangements: a short synthesis of the antiherpes agent 2’-deoxy-5-ethyl-4’-thiouridine via direct coupling of a silylated pyrimidine base with a 4-thiopyranose sugar. J. Org. Chem. 1995, 60, 5170–5173.
  • Elgemeie, G.H.; Hussein, M.M.; Al-Khursani, S.A. A total synthesis of a new class of biazine thioglycosides. J. Carbohydr. Chem. 2004, 23, 465–475.
  • 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, 65c, 577–587.
  • 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. 1977, 51, 1024–1033.
  • Elgemeie, G.H.; Attia, A. A new class of dihydropyridine thioglycosides via piperdinium salts. Synth. Commun. 2003, 33, 2243–2255.
  • Elgemeie, G.H.; Ali, H.A.; Elghandour, A.H.; Abd-Elaziz, G.W. Synthesis of novel derivatives of 4-methylthio-N-aryl-2-pyridone and deazapurine analogues: The reaction of ketene dithioacetals with substituted acetanilides. Phosphorus, Sulfur Silicon 2000, 164, 189–197.
  • Mosmann, T. Rapid colorimetric assay for cellular growth and survival: Application to proliferation and cytotoxicity assays. J. Immunol. Methods 1983, 65, 55–63.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.