V-PROLI/NO, a Prodrug of the Nitric Oxide Donor, PROLI/NO
- 20 July 2007
- journal article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 9 (17) , 3409-3412
- https://doi.org/10.1021/ol701419a
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 O2-vinyl derivative, V-PROLI/NO. Metabolism of V-PROLI/NO by liver microsomes enriched in human cytochrome P450 isoforms was demonstrated.Keywords
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