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An improved synthesis of V-PROLI/NO, a cytochrome P450-activated nitric oxide prodrug

  1. Author:
    Hong, S. Y.
    Nandurdikar, R. S.
    Keefer, L. K.
    Saavedra, J. E.
    Chakrapani, H.

  2. Author Address

    Saavedra, Joseph E.] NCI, Basic Sci Program, SAIC Frederick, Frederick, MD 21702 USA. [Hong, Sam Y.; Nandurdikar, Rahul S.; Keefer, Larry K.; Chakrapani, Harinath] NCI, Chem Sect, Comparat Carcinogenesis Lab, Frederick, MD 21702 USA.
    1. Year: 2009
  2. Journal: Tetrahedron Letters
    1. 50
    2. 31
    3. Pages: 4545-4548
  4. Type of Article: Article
  1. Abstract:

    An improved synthesis of V-PROLI/NO, a cytochrome P450-activated nitric oxide (NO) prodrug, in an overall yield of 26% in four steps from prolinol is reported: the previously published yield of this transformation was 1%. Using this revised strategy, the sarcosine analogue (14) of V-PROLI/NO was prepared. Finally, the methyl ester of V-PROLI/NO (15) was found to be an esterase-activated prodrug form of V-PROLI/NO. Published by Elsevier Ltd.

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  2. DOI: 10.1016/j.tetlet.2009.05.089
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