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

✍ Scribed by Sam Y. Hong; Rahul S. Nandurdikar; Larry K. Keefer; Joseph E. Saavedra; Harinath Chakrapani

Book ID
104096640
Publisher
Elsevier Science
Year
2009
Tongue
French
Weight
541 KB
Volume
50
Category
Article
ISSN
0040-4039

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✦ Synopsis

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.

πŸ“œ SIMILAR VOLUMES

Injectable formulation of disodium 1-[2-
Injectable formulation of disodium 1-[2-(carboxylato)pyrrolidin-1-yl]diazen-1-ium-1,2-diolate (PROLI/NO), an ultrafast nitric oxide donor prodrug
✍ David J. Waterhouse; Joseph E. Saavedra; Keith M. Davies; Michael L. Citro; Xia πŸ“‚ Article πŸ“… 2006 πŸ› John Wiley and Sons 🌐 English βš– 105 KB

PROLI/NO is an agent of structure XN(O)==NONa (X = L-prolyl) whose 2-s half-life for nitric oxide (NO) release at physiological pH makes it an excellent prodrug for localizing NO's therapeutic effects at the site of application, but a difficult one to formulate and certify as pure. Despite its extra