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V-PROLI/NO, a prodrug of the nitric oxide donor, PROLI/NO

  1. Author:
    Chakrapani, H.
    Showalter, B. M.
    Kong, L.
    Keefer, L. K.
    Saavedra, J. E.

  2. Author Address

    NCI, Comparat Carcinogenesis Lab, Chem Sect, Frederick, MD 21702 USA. NCI, SAIC Frederick, Basic Res Program, Frederick, MD 21702 USA.;Saavedra, JE, NCI, Comparat Carcinogenesis Lab, Chem Sect, Frederick, MD 21702 USA.;saavj@ncifcrf.gov
    1. Year: 2007
    2. Date: Aug
  2. Journal: Organic Letters
    1. 9
    2. 17
    3. Pages: 3409-3412
  4. Type of Article: Article
  5. ISSN: 1523-7060
  1. Abstract:

    The sensitivity to decomposition of the nitric oxide (NO) donor ion, 1-[2-(carboxylato)pyrrolidin-1-yl]diazen-1-ium-1,2-diolate (PROLI/NO), complicates direct electrophilic substitution to form useful prodrug derivatives. A modified general synthetic approach involving 1-[2-(hydroxymethyl)pyrrolidin-1-yl]diazen-1-ium-1,2-diolate ion (structure A, above) was used to prepare several PROLI/NO prodrugs including the previously inaccessible O-2-vinyl derivative, V-PROLI/NO. Metabolism of V-PROLI/NO by liver microsomes enriched in human cytochrome P450 isoforms was demonstrated.

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External Sources

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  2. DOI: 10.1021/ol701419a
  3. View record in Web of Science®
  4. WOS: 000248658800054

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