Abstract
We report an indirect method for synthesis of previously inaccessible diazeniumdiolated carbamates. Synthesis involves use of previously reported triisopropylsilyloxymethylated isopropylamine diazeniumdiolate (TOM-ylated IPA/NO). These novel diazeniumdiolated carbamate prodrugs upon activation release nitric oxide (NO) similar to their secondary amine counterparts. They are also efficient sources of intracellular NO. These prodrugs may have potential applications as therapeutic NO-donors.
Copyright © 2012 Elsevier Ltd. All rights reserved.
Publication types
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Research Support, N.I.H., Extramural
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Research Support, N.I.H., Intramural
MeSH terms
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Azo Compounds / chemical synthesis
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Azo Compounds / chemistry
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Azo Compounds / pharmacology
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Carbamates / chemical synthesis
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Carbamates / chemistry*
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Carbamates / pharmacology*
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Cell Line
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Chemistry Techniques, Synthetic / methods
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Fibroblasts / drug effects
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Fibroblasts / metabolism
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Humans
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Nitric Oxide / metabolism
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Nitric Oxide Donors / chemical synthesis
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Nitric Oxide Donors / chemistry*
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Nitric Oxide Donors / pharmacology*
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Prodrugs / chemical synthesis
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Prodrugs / chemistry*
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Prodrugs / pharmacology*
Substances
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Azo Compounds
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Carbamates
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Nitric Oxide Donors
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Prodrugs
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diazeniumdiolate
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Nitric Oxide