Researchers of the Zelinsky Institute have obtained effective nitrogen monoxide donors

Nitric oxide (NO) is one of the signaling molecules in animal and human biology, playing various roles in both physiology and pathophysiology. NO exhibits vasodilating activity, inhibits platelet adhesion and aggregation, and has other anti-inflammatory properties. The discovery of such diverse biochemical roles for NO has stimulated the search for chemical compounds capable of releasing NO under physiological conditions, which besides must be resistant to hydrolysis and safely stored.

Scientists from the Laboratory of Nitrogen-Containing Compounds of the ZIOC have developed a simple and effective approach to the synthesis of hybrid structures consisting of fragments of the two most promising heterocyclic NO donors: furoxans and sydnonimines. The key step in the process is the NOBF4-mediated nitrosation-cyclization of α-aminonitriles. The developed method excludes the formation of carcinogenic N-nitrosamines as intermediates and is compatible with a wide range of initial substrates. As a result, fully substituted sydnonimines linked to the furoxan ring directly through a carbon-carbon bond or through various linkers can be obtained. The synthesized hybrid structures have demonstrated a promising ability to release NO under physiological conditions. The combination of ease of their synthesis and high NO-donor capacity has significant potential for their use in pharmacology and various biochemical applications.
 

Source:

Alexander D. Shuvaev, Egor S. Zhilin, Leonid L. Fershtat NOBF4-mediated Assembly of the Sydnone Imine Scaffold in the Synthesis of Double Nitric Oxide Donors // Synthesis, 2023, accepted manuscript. DOI: 10.1055/a-2011-7264.