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Click Reaction in Conjunction with Diazeniumdiolate Chemistry: Developing High-Load Nitric Oxide Donors

  1. Author:
    Oladeinde, O. A.
    Hong, S. Y.
    Holland, R. J.
    Maciag, A. E.
    Keefer, L. K.
    Saavedra, J. E.
    N, urdikar

  2. Author Address

    [Maciag, Anna E.; Saavedra, Joseph E.] NCI, Basic Sci Program, SAIC Frederick, Frederick, MD 21702 USA. [Oladeinde, Oyebola A.; Hong, Sam Y.; Holland, Ryan J.; Keefer, Larry K.; Nandurdikar, Rahul S.] NCI, Chem Sect, Comparat Carcinogenesis Lab, Frederick, MD 21702 USA.;Saavedra, JE, NCI, Basic Sci Program, SAIC Frederick, Frederick, MD 21702 USA.;saavedjo@mail.nih.gov nandurdikarr@mail.nih.gov
    1. Year: 2010
    2. Date: Oct
  2. Journal: Organic Letters
    1. 12
    2. 19
    3. Pages: 4256-4259
  4. Type of Article: Article
  5. ISSN: 1523-7060
  1. Abstract:

    The use of Cu(I)-catalyzed "click" reactions of alkyne-substituted diazeniumdiolate prodrugs with bis- and tetrakis-azido compounds is described. The "click" reaction for the bis-azide using CuSO4/Na-ascorbate predominantly gave the expected bis-triazole. However, CuI/diisopropylethylamine predominantly gave uncommon triazolo-triazole products as a result of oxidative coupling. Neither set of "click" conditions showed evidence of compromising the integrity of the diazeniumdiolate groups. The chemistry developed has applications in the synthesis of polyvalent and dendritic nitric oxide donors.

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External Sources

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  2. DOI: 10.1021/ol101645k
  3. View record in Web of Science®
  4. WOS: 000282041900011

Library Notes

  1. Fiscal Year: FY2010-2011
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