Synthesis and Potent Anti-leukemic Activity of Novel 5'-Norcarbocyclic C-nucleoside Phosphonic Acids

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 p...

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Bibliographic Details
Published in:Bulletin of the Korean Chemical Society 2014, 35(12), , pp.3502-3508
Main Authors: Kim, Seyeon, Kim, Eunae, Oh, Chang-Hyun, Yoo, Kyung Ho, Hong, Joon Hee
Format: Article
Language:English
Subjects:
화학
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Summary: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. KCI Citation Count: 2
ISSN:0253-2964
1229-5949
DOI:10.5012/bkcs.2014.35.12.3502