Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Synthesis and Potent Anti-leukemic Activity of Novel 5'-Norcarbocyclic C-nucleoside Phosphonic Acids

  • Kim, Seyeon (BK21-Project Team, College of Pharmacy, Chosun University) ;
  • Kim, Eunae (BK21-Project Team, College of Pharmacy, Chosun University) ;
  • Oh, Chang-Hyun (Center for Biomaterials, Korea Institute of Science and Technology) ;
  • Yoo, Kyung Ho (Chemical Kinomics Research Center, Korea Institute of Science and Technology) ;
  • Hong, Joon Hee (BK21-Project Team, College of Pharmacy, Chosun University)
  • Received : 2014.07.28
  • Accepted : 2014.08.14
  • Published : 2014.12.20
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Abstract

The first synthetic route to 5'-norcarbocyclic C-nucleoside [7-oxa-7,9-dideazadenosine (furo[3,2-d]pyrimidine) and 9-deazaadenosine (pyrrolo[3,2-d]pyrimidine)] phosphonic acids from commercially available 1,3-dihydroxy cyclopentane was described. The key C-C bond formation from sugar to base precursor was performed using Knoevenagel-type condensation from a ketone derivative. Synthesized C-nucleoside phosphonic acids were tested for anti-HIV activity as well as anti-leukemic activity. Compound 26 showed significant anti-leukemic activity.

Keywords

References

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