Reactions of nitroxides, part 7: Synthesis of novel nitroxide selenoureas

Abstract

ABSTRACT:The reactions of 4-isoselenocyanato-2,2,6,6-tetramethylpiperidine-1-oxyl

Synthesis and biological applications of selenoureas

“…Nitroxyl‐bearing selenoureas were offered by reacting 4‐isoselenocyanato‐2,2,6,6‐tetramethylpiperidine‐1‐oxyl with selected amines . The starting material for the synthesis of 4‐isoselenocyanato‐2,2,6,6‐tetramethylpiperidine‐1‐oxyl was 4‐amino‐2,2,6,6‐tetramethylpiperidine‐1‐oxyl, which was converted to 4‐formyl‐2,2,6,6‐tetramethylpiperidine‐1‐oxyl by reacting it with excess ethyl formate .…”

Reactions of Nitroxides, Part 17. Synthesis, Fungistatic and Bacteriostatic Activity of Novel Five- and Six-Membered Nitroxyl Selenoureas and Selenocarbamates

“…Selenoureas showed free-radical scavenging [10,11,12], and enzyme inhibition [10,11,13,14,15,16] potential. They demonstrated anticancer [10,11,17], DNA binding [17,18,19,20], antioxidant [17,18,21,22,23], antibacterial [18], antifungal [18,24,25,26], and herbicidal [25] properties.…”

“…Selenoureas served as starting materials to the synthesis of further organoselenium derivatives [59]. Selenocarbamates showed antiproliferative [60], cytotoxic [61], antioxidant [22], pesticidal [24,26], and effective superoxide anion scavenger [62] activities. Selenocarbamates were obtained by addition reaction of isoselenocyanate with alcohols [54,63].…”

“…Methyl and ethyl nitroxyl selenocarbamates were obtained from 4-isoselenocyanato-2,2,6,6-tetramethylpiperidine-1-oxyl, by the reaction with either sodium methoxide or ethoxide, in methanol or ethanol, respectively [26]. The biological action of nitroxyl radicals was well documented [64,65,66,67].…”

Reactions of nitroxides, part XI: O‐Aryl phenylselenophosphonates bearing a nitroxyl moiety

“…In spite of that, attempts to apply selenium‐containing compounds as insecticides: beta‐selenolactams 13 and selenophosphates 12 were described. Recently, we have investigated antifungal properties of the selenoureas bearing a nitroxyl moiety 14. Because there are only a few examples of nitroxyl radicals containing a selenium atom 15,16 or P=Se moiety 17,18, we are encouraged to continue the investigation of the antifungal properties of the nitroxyl radicals with a P=Se function.…”