Advanced search
Publication Cover
Bioscience, Biotechnology, and Biochemistry Volume 63, 1999 - Issue 4
Journal homepage
157
Views
5
CrossRef citations to date
0
Altmetric
Original Articles

Synthesis of 4′-C-Ethynyl-β-D-ribo-pentofuranosyl Pyrimidines

Ritsuko YAMAGUCHIDepartment of Applied Biological Chemistry, Faculty of Agriculture, Tohoku University
,
Tatsuma IMANISHIDepartment of Applied Biological Chemistry, Faculty of Agriculture, Tohoku University
,
Satoru KOHGODepartment of Applied Biological Chemistry, Faculty of Agriculture, Tohoku University
,
Hiroko HORIEDepartment of Applied Biological Chemistry, Faculty of Agriculture, Tohoku University
&
Hiroshi OHRUIDepartment of Applied Biological Chemistry, Faculty of Agriculture, Tohoku University
Pages 736-742 | Received 09 Nov 1998, Accepted 21 Dec 1998, Published online: 22 May 2014

  • 1) Goodman, B. K., and Greenberg, M. M., Independent generation and reactivity of 2′-deoxyurid-1′-yl. J. Org. Chem., 61, 2-3 (1996).
  • 2) Auguste, S. P., and Young, D. W., Synthesis of uridine derivatives containing strategically placed radical traps as potential inhibitors of ribonucleotide reductase. J. Chem. Soc., Perkin Trans. 1, 395-404 (1995).
  • 3) Beigelman, L., Karpeisky, A., Matulic-Adamic, J., Haeberi, P., Sweedler, D., and Usmann, N., Synthesis of 2′-modified nucleotides and their incorporation into hammerhead ribozyme. Nucleic Acids Res., 23, 4434-4442 (1995).
  • 4) Azuma, A., Hanaoka, K., Kurihara, A., Kobayashi, T., Miyauchi, S., Kano, N., Tanaka, M., Sasaki, T., and Matsuda, A., Nucleosides and nucleotides. 141. Chemical stability of new antitumor nucleosides. 2′-C-Cyano-2′-deoxy-1-β-D-arabino-pentofuranosylcytosine in alkaline medium: Formation of 2′-C-Cyano-2′-deoxy-1-β-D-ribo-pentofuranosylcytosine and its antitumor activity. J. Med. Chem., 38, 3391-3397 (1995).
  • 5) Hassan, A. E. A., Nishizono, N., Minakawa, N., Shuto, S., and Matsuda, A., Nucleosides and nucleotides. 151. Conversion of (Z)-2′-(cyanomethylene)-2′-deoxyuridines into their (E)-isomers via addition of thiophenol to the cyanomethylene moiety followed by oxidative syn-elimination reaction. J. Org. Chem., 61, 1368-1375 (1996).
  • 6) Hattori, H., Tanaka, M., Fukushima, M., Sasaki, T., and Matsuda, A., Nucleosides and nucleotides. 158. 1-(3-C-Ethynyl-β-D-ribo-pentofuranosyl)cytosine, 1-(3-C-ethynyl-β-D-ribo-pentofuranosyl)uracil, and their nucleobase analogues as new potential multifunctional antitumor nucleosides with a broad spectrum of activity. J. Med. Chem., 39, 5005-5011 (1996).
  • 7) Youssefyeh, R. D., Verheyden, P. H., and Moffatt, J. G., 4′-Substituted nucleosides. 4. Synthesis of some 4′-hydroxymethyl nucleosides. J. Org. Chem., 44, 1301-1309 (1979).
  • 8) Waga, T., Nishizaki, T., Miyakawa, I., Ohrui, H., and Meguro, H., Synthesis of 4′-C-methylnucleosides. Biosci. Biotechnol. Biochem., 57, 1433-1438 (1993).
  • 9) O-Yang, C., Wu, H. Y., Fraser-Smith, W. B., and Walker, K. A. M., Synthesis of 4′-cyanothymidine and analogs as potent inhibitors of HIV. Tetrahedron Lett., 33, 37-40 (1992).
  • 10) Thrane, H., Fensholdt, J., Regner, M., and Wengel, J., Novel linear and branched oligodeoxynucleotide analogues containing 4′-C-(hydoroxymethyl)thymidine. Tetrahedron, 51, 10389-10402 (1995).
  • 11) Waga, T., Ohrui, H., and Meguro, H., Synthesis and biological evaluation of 4′-C-methylnucleosides. Nucleosides Nucleotides, 15, 287-304 (1996).
  • 12) Yamaguchi, T., Tomikawa, A., Hirai, T., Kawaguchi, T., Ohrui, H., and Saneyoshi, M., Antileukemic activities and mechanism of action of 2′-deoxy-4′-methylcytidine and related nucleosides. Nucleosides Nucleotides, 16, 1347-1350 (1997).
  • 13) Kitano, K., Miura, S., Ohrui, H., and Meguro, H., Synthesis of 4′-C-fluoromethylnucleosides as potential antineoplastic agents. Tetrahedron, 53, 13315-13322 (1997).
  • 14) Corey, E. J., and Fuchs, P. L., A synthetic method for formyl-ethynyl conversion. Tetrahedron Lett., 36, 3769-3772 (1972).
  • 15) Vorbruggen, H., Krolikiewicz, K., and Bennua, B., Nucleoside synthesis with trimethylsilyl triflate and perchlorate as catalysts. Chem. Ber., 114, 1234-1247 (1981).
  • 16) Lemieux, R. U., Lineback, D. R., Chemistry of the carbohydrates. Ann. Rev. Biochem., 32, 155-178 (1963).
  • 17) Baker, D. C., Horton, C. G., and Tindall, C. G., Large-scale preparation of D-allose: observations on the stereoselectivity of the reduction of 1, 2: 5, 6-di-O-isopropylidene-α-D-ribo-hexofuranos-3-ulose hydrate. Carbohyd. Res., 24, 192-197 (1972).
  • 18) Divaker, K. J., and Reese, C. B., 4-(1, 2, 4-Triazole-1-yl)- and 4-(3-nitro-1, 2, 4-triazole-1-yl)-1-(β-D-2, 3, 5-tri-O-acetylarabinofuranosyl)pyrimidine-2(1H)-ones. Valuable intermediates in the synthesis of derivatives of 1-(β-D-arabinofuranosyl)cytosine (ara-C). J. Chem. Soc., Perkin Trans. 1, 1171-1176 (1982).

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:

Order Reprints Request Corporate Permissions

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:

Request Academic Permissions

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.

Related research

People also read lists articles that other readers of this article have read.

Recommended articles lists articles that we recommend and is powered by our AI driven recommendation engine.

Cited by lists all citing articles based on Crossref citations.
Articles with the Crossref icon will open in a new tab.