Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 51, 2021 - Issue 3
138
Views
3
CrossRef citations to date
0
Altmetric
Articles

Synthesis of hexopyranosyl pyrimidine homonucleosides

, , , &
Pages 446-452 | Received 11 Jun 2020, Published online: 25 Oct 2020

References

  • Break, L. M.; Mohamed, M. A. M.; Al-Thubaiti, O. A. A.; Eibaih, F. E. M. Nucleosides 10: Synthesis of New Derivatives of Pyrimidine Nucleosides of Expected Biological Activity. IJOC 2019, 09, 107–120. DOI: 10.4236/ijoc.2019.93010.
  • Trznadel, R.; Singh, A.; Kleczewska, N.; Liberska, J.; Ruszkowski, P.; Celewicz, L. Synthesis and in Vitro Anticancer Activity of New Gemcitabine-Nucleoside Analogue Dimers Containing Methyltriazole or Ester-Methyltriazole Linker. Bioorg. Med. Chem. Lett. 2019, 29, 2587–2594. DOI: 10.1016/j.bmcl.2019.08.003.
  • Li, X.; Dumbre, S. G.; Lescrinier, E.; Groaz, E.; Herdewijn, P. Synthesis and Conformation of Pentopyranoside Nucleoside Phosphonates. J. Org. Chem. 2019, 84, 6589–6603. DOI: 10.1021/acs.joc.8b03178.
  • Epple, R.; Kudirka, R.; Greenberg, W. A. Solid-Phase Synthesis of Nucleoside Analogues. J. Comb. Chem. 2003, 5, 292–310. DOI: 10.1021/cc020087f.
  • 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. 2013, 12, 447–464. DOI: 10.1038/nrd4010.
  • Aerschot Van, A.; Verheggen, I.; Hendrix, C.; Herdewijn, P. 1,5-Anhydrohexitol Nucleic Acids, a New Promising Antisense Construct. Angew. Chem. Int. Ed. Engl. 1995, 34, 1338–1339. DOI: 10.1002/anie.199513381.
  • Eschenmoser, A. Chemical Etiology of Nucleic Acid Structure. Science 1999, 284, 2118–2124. DOI: 10.1126/science.284.5423.2118.
  • Malinovskii, V. L.; Wenger, D.; Haner, R. Nucleic Acid-Guided Assembly of Aromatic Chromophores. Chem. Soc. Rev. 2010, 39, 410–422. DOI: 10.1039/b910030j.
  • Bandy, T. J.; Brewer, A.; Burns, J. R.; Marth, G.; Nguyen, T.; Stulz, E. DNA as Supramolecular Scaffold for Functional Molecules: Progress in DNA Nanotechnology. Chem. Soc. Rev. 2011, 40, 138–148. DOI: 10.1039/b820255a.
  • Deleavey, G. F.; Damha, M. Designing Chemically Modified Oligonucleotides for Targeted Gene Silencing. J. Chem. Biol. 2012, 19, 937–954. DOI: 10.1016/j.chembiol.2012.07.011.
  • Hornum, M.; Sharma, P. K.; Jacobsen, C. R.; Kumar, P.; Petersen, M.; Nielsen, P. Condensing the Information in DNA with Double-Headed Nucleotides. Chem. Commun. 2017, 53, 9717–9720. DOI: 10.1039/c7cc05047j.
  • Sharma, P. K.; Kumar, P.; Nielsen, P. Double-Headed Nucleotides: Building Blocks for New Nucleic Acid Architectures. Aust. J. Chem. 2016, 69, 1094–1101. DOI: 10.1071/CH16021.
  • Christensen, M. S.; Madsen, C. M.; Nielsen, P. Synthesis and Modelling of DNA Junction and Minor Groove Zipper Motifs Incorporating the Double-Headed Nucleoside 5'(S)-C-(thymine-1-ylmethyl)thymidine. Org. Biomol. Chem. 2007, 5, 1586–1594. DOI: 10.1039/b700852j.
  • Pedersen, S. L.; Nielsen, P. Stabilisation of Nucleic Acid Secondary Structures by Oligonucleotides with an Additional Nucleobase; Synthesis and Incorporation of 2´-Deoxy-2´-C-(2-(Thymine-1-yl)Ethyl)Uridine. Org. Biomol. Chem. 2005, 3, 3570. DOI: 10.1039/b510167k.
  • Kumar, S.; Steffansen, S. I.; Albaek, N.; Nielsen, P. Synthesis of Bicyclic Double-Headed Nucleoside. Tetrahedron 2014, 70, 583–589. DOI: 10.1016/j.tet.2013.12.013.
  • Wu, T.; Nauwelaerts, K.; Van Aerschot, A.; Froeyen, M.; Lescrinier, E.; Herdewijn, P. Base-Base Interactions in the Minor Groove of Double-Stranded DNA. J. Org. Chem. 2006, 71, 5423–5431. DOI: 10.1021/jo052194c.
  • Wu, T.; Froeyen, M.; Schepers, G.; Mullens, K.; Rozenski, J.; Busson, R.; Aerschot, A. V.; Herdewijn, P. Synthesis and Stability of Oligonucleotides Containing Acyclic Achiral Nucleoside Analogues with Two Base Moieties. Org. Lett. 2004, 6, 51–54. DOI: 10.1021/ol0360647.
  • Andersen, C.; Sharma, P. K.; Christensen, M. S.; Pedersen, N. S.; Nielsen, P. Synthesis of Double-Headed Nucleosides with the Additional Nucleobase in the 5´-C-Position. Nucleic Acids Symp. Ser. 2008, 52, 275–276. DOI: 10.1093/nass/nrn139.
  • Kiritsis, C.; Manta, S.; Papasotiriou, I.; Argyropoulou, E. C.; Trakossas, S.; Balzarini, J.; Komiotis, D. Synthesis and Biological Evaluation of 3′-C-ethynyl and 3′-C-(1,4-Disubstituted-1,2,3-triazolo) Double-Headed Pyranonucleosides. Med. Chem. 2012, 8, 320–329. DOI: 10.2174/157340612800786624.
  • Khatri, V.; Kumar, A.; Singh, B.; Malhotra, S.; Prasad, A. K. Synthesis of β-C-Glycopyranosyl Aldehydes and 2,6-Anhydro-Heptitols. J. Org. Chem. 2015, 80, 11169–11174. DOI: 10.1021/acs.joc.5b01933.
  • El-Dossoki, F. I. The Effect of 18-Crown-6 on the Solubility and Thermodynamic Parameters of Li2CO3, Na2CO3, NaCl, CH3COONa and KCl in Methanol and Ethanol. Indian J. Chem. 2005, 44A, 1594–1596.
  • Kikuchi, Y.; Sakamoto, Y. Complex Formation of Alkali Metal Ions with 18-Crown-6 and Its Derivatives in 1,2-Dichloroethane. Anal. Chim. Acta 2000, 403, 325–332. DOI: 10.1016/S0003-2670(99)00648-0.
  • Solov’ev, V. P.; Strakhova, N. N.; Raevsky, O. A.; Rudiger, V.; Schneider, H. J. Solvents Effects on Crown Ether Complexations. J. Org. Chem. 1996, 61, 5221–5226. DOI: 10.1021/jo952250h.

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.