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Novel protection-deprotection strategies in diazeniumdiolate chemistry: synthesis of V-IPA/NO

  1. Author:
    Nandurdikar, R. S.
    Keefer, L. K.
    Saavedra, J. E.

  2. Author Address

    [Nandurdikar, RS; Keefer, LK] Natl Canc Inst, Chem Sect, Comparat Carcinogenesis Lab, Frederick, MD 21702 USA [Saavedra, JE] Natl Canc Inst, Basic Sci Program, SAIC Frederick Inc, Frederick, MD 21702 USA;Nandurdikar, RS (reprint author), Natl Canc Inst, Chem Sect, Comparat Carcinogenesis Lab, Frederick, MD 21702 USA;nandurdikarr@mail.nih.gov
    1. Year: 2011
    2. Date: Jun 21
  2. Journal: Chemical Communications
    1. 47
    2. 23
    3. Pages: 6710-6712
  4. Type of Article: Article
  5. ISSN: 1359-7345
  1. Abstract:

    Synthesis of previously inaccessible, potentially liver selective HNO donor V-IPA/NO ([iPrHN(3)-N(1)(O(1))=N(2)-O(2)-R], where R = vinyl) is reported here. A novel fluoride-labile TOM group at O-2 in conjunction with MOM protection at N-3 in IPA/NO is employed. The strategy developed is also extended to synthesis of other NO-releasing prodrugs and has applications in diversity-oriented synthesis of HNO- and NO-prodrugs.

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External Sources

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  2. DOI: 10.1039/c1cc12130h
  3. View record in Web of Science®
  4. WOS: 000291113000059

Library Notes

  1. Fiscal Year: FY2010-2011
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