Improved synthesis of V-PYRRO/NO, a liver-selective nitric oxide prodrug, and analogues |
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Authors: | Sam Y. Hong Larry K. Keefer |
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Affiliation: | a Chemistry Section, Laboratory of Comparative Carcinogenesis, National Cancer Institute at Frederick, Frederick, MD 21702, USA b Basic Research Program, SAIC-Frederick, National Cancer Institute at Frederick, Frederick, MD 21702, USA |
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Abstract: | The reported synthesis of O2-vinyl 1-(pyrrolidin-1-yl)diazen-1-ium-1,2-diolate (V-PYRRO/NO), a hepatoprotective agent, was cumbersome and limited by a poor overall yield of 4% from sodium 1-(pyrrolidin-1-yl)diazen-1-ium-1,2-diolate (PYRRO/NO). We report an improved synthesis of V-PYRRO/NO in two steps with a significantly higher overall yield of 40% from PYRRO/NO. Using this protocol, a number of structural analogues of V-PYRRO/NO were prepared in good yields. |
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