Organoselenium Compounds: Chemistry and Applications in Organic Synthesis

Abstract

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.

4-(Phenylselanyl)-2H-chromen-2-one-Loaded Nanocapsule Suspension—A Promising Breakthrough in Pain Management: Comprehensive Molecular Docking, Formulation Design, and Toxicological and Pharmacological Assessments in Mice

“…The lipophilic nature of the 4-PSCO molecule is recognized for its association with critical criteria such as gastrointestinal permeability, blood–brain barrier passage, and plasma protein binding [ 86 ]. Indeed, it has already been described in the literature that the presence of the selenium atom, as well as the coumarin nucleus in the structure of organic compounds, gives them high lipophilicity [ 87 , 88 ]. In this study, the lipophilic properties of 4-PSCO, coupled with the selection of ethylcellulose polymer, aligned with the promising effects of the formulated nanocapsules.…”

Photoredox-Catalyzed Synthesis of C-Benzoselenazolyl/Benzothiazolyl Glycosides from 2-Isocyanoaryl Selenoethers/Thioethers and Glycosyl Bromides

“…Se, as a trace element closely related to human health, is involved in many biomolecules, such as selenoproteins, Se-nucleosides, and selenosugars . Due to the low toxicity and easily absorbed form, organoselenium compounds, especially selenoglycosides, have received extensive attention. As shown in Figure a, acetylated-selenoglycosides (AcSG) are effective activators of protein phosphatase-1 (PP1) and -2A (PP2A) .…”

Aminoselenation and Dehydroaromatization of Cyclohexanones with Anilines and Diselenides

“…The ortho-substituted aryl selenides not only serve as fundamental scaffolds in numerous lead compounds, bioactive molecules, and functional materials (Scheme A), but also hold potential as bioisosteres . Due to the presence of two different substituents at adjacent positions on the benzene ring, traditional construction methods such as electrophilic substitution reactions, coupling reactions, and C–H functionalization are quite challenging, requiring multiple reaction steps and encountering regioselectivity issues .…”