Organoselenium Compounds: Chemistry and Applications in Organic Synthesis

Selenium, originally described as a toxin, turns out to be a crucial trace element for life that appears as selenocysteine and its dimer, selenocystine. From the point of view of drug developments, selenium-containing drugs are isosteres of sulfur and oxygen with the advantage that the presence of the selenium atom confers antioxidant properties and high lipophilicity, which would increase cell membrane permeation leading to better oral bioavailability. In this article, we have focused on the relevant features of the selenium atom, above all, the corresponding synthetic approaches to access a variety of organoselenium molecules along with the proposed reaction mechanisms. The preparation and biological properties of selenosugars, including selenoglycosides, selenonucleosides, selenopeptides, and other selenium-containing compounds will be treated. We have attempted to condense the most important aspects and interesting examples of the chemistry of selenium into a single article.

Automated summary

Originally described as a toxin, selenium is now recognized as a crucial trace element for life. Selenium-containing drugs have advantages over sulfur and oxygen isosteres, as the presence of selenium confers antioxidant properties and high lipophilicity, improving oral bioavailability. This article focuses on the features of selenium atom and synthetic approaches to various organoselenium compounds, as well as their proposed reaction mechanisms. The preparation and biological properties of selenosugars, including selenoglycosides, selenonucleosides, selenopeptides, and other selenium-containing compounds are discussed.