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Synthesis of conformationally locked carbocyclic 1,3-diazepinone nucleosides as inhibitors of cytidine deaminase

  1. Author:
    Ludek, O. R.
    Schroeder, G. K.
    Wolfenden, R.
    Marquez, V. E.

  2. Author Address

    Laboratory of Medicinal Chemistry, Center for Cancer Research, National Cancer Institute at Frederick, National Institutes of Health, Frederick, MD 21702, USA.
    1. Year: 2008
    2. Epub Date: 9/9/2008
  2. Journal: Nucleic acids symposium series (2004)
    1. 52
    2. Pages: 659-60
  4. Type of Article: Article
  5. ISSN: 1746-8272 (Electronic);0261-3166 (Linking)
  1. Abstract:

    We synthesized a series of carbocyclic nucleoside inhibitors of cytidine deaminase (CDA) based on a seven-membered 1,3-diazepin-2-one moiety. In the key step, the seven-membered ring was formed by a ring-closing-metathesis reaction. Therefore, the bis-allyl-urea moiety had to be protected by benzoylation in order to obtain an orientation suitable for ring closure. To our surprise, the analogue built on a flexible sugar template (4) showed a 100-fold stronger inhibition of CDA than the derivative with the preferred south-conformation.

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External Sources

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  2. DOI: 10.1093/nass/nrn333
  3. PMID: 18776552
  4. PMCID: PMC2730941
  5. NIHMSID: Nihms120298

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