C-nitroso compounds: synthesis, physicochemical properties and biological activities.

Journal Article (Review;Journal Article)

Because of the chemical and physical properties of nitric oxide, its effective use and delivery for therapeutic application represents a significant challenge. Accordingly, current understanding of nitric oxide biology largely stems from the use of nitric oxide prodrugs and adducts whose biological activities are based on their ability to release nitric oxide or a redox-related species. Among the structurally diverse ensemble of nitric oxide donor compounds reported to date are the C-nitroso compounds. These compounds have only recently been investigated with respect to their potential as nitric oxide donors, although they have been known and studied for over 120 years. Here, we consider the synthesis and physico-chemical properties of the C-nitroso compounds and the available data regarding their biological activities. Synthetic methods reviewed include direct substitution of H by NO, oxidative approaches, and the addition of various oxides of nitrogen across multiple bonds. The electronic spectra of C-nitroso compounds and the mechanism and thermodynamics of monomer-dimer equilibration are described. The physico-chemical and biological properties of two related classes of compounds, the diazetine dioxides and the furoxans, are also described.

Full Text

Duke Authors

Cited Authors

  • Gooden, DM; Chakrapani, H; Toone, EJ

Published Date

  • January 2005

Published In

Volume / Issue

  • 5 / 7

Start / End Page

  • 687 - 705

PubMed ID

  • 16101429

Pubmed Central ID

  • 16101429

Electronic International Standard Serial Number (EISSN)

  • 1873-4294

International Standard Serial Number (ISSN)

  • 1568-0266

Digital Object Identifier (DOI)

  • 10.2174/1568026054679353


  • eng