Nitrate Esters as Nitric Oxide Donors:  SS-Nitrates

The important biological secondary messenger NO can be generated from exogenous nitrovasodilators and NO donors. Nitrate esters are nitrovasodilators and NO mimetics, believed to be biotransformed to NO in vivo. On the basis of a mechanistic hypothesis, nitrates have been synthesized that release NO...

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Bibliographic Details
Published in:Organic letters 2001-04, Vol.3 (8), p.1113-1116
Main Authors: Zavorin, Sergei I, Artz, Jennifer D, Dumitrascu, Adina, Nicolescu, Adrian, Scutaru, Dan, Smith, Stefanie V, Thatcher, Gregory R. J
Format: Article
Language:English
Subjects:
Electrochemistry
Esters - chemistry
Models, Chemical
Nitric Oxide - chemistry
Sulfhydryl Compounds - chemistry
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Summary:The important biological secondary messenger NO can be generated from exogenous nitrovasodilators and NO donors. Nitrate esters are nitrovasodilators and NO mimetics, believed to be biotransformed to NO in vivo. On the basis of a mechanistic hypothesis, nitrates have been synthesized that release NO at significant rates in neutral aqueous solution in the presence only of added thiol. The novel masked β-mercaptonitrates reported (SS-nitrates), provide information on possible sulfhydryl-dependent biotransformation mechanisms for nitrates in clinical use.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol007022a