Over the last two decades, fluorine substitution has become one of the essential structural traits in modern pharmaceuticals. Thus, about half of the most successful drugs (blockbuster drugs) contain fluorine atoms. In this review, we profile 17 fluorine‐containing drugs approved by the food and drug administration (FDA) in 2018. The newly approved pharmaceuticals feature several types of aromatic F and CF3, as well as aliphatic (CF2) substitution, offering advances in the treatment of various diseases, including cancer, HIV, malarial and smallpox infections.

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cyclizations · homogeneous catalysis · oxidation · seleniumApplications of selenium reagents in organic chemistry have developed rapidly over the past years, and comprehensive reviews on this area have appeared.[1] Rather new, however, is the use of selenium-based catalysts in organic synthesis. We highlight new developments in organoselenium catalysis and in particular the use of selenium electrophiles and organoselenium compounds in carbonylation reactions and the oxidation of alkenes and carbonyl compounds. The use of organoselenium ligands for metal-catalyzed processes is not covered here; the topic has been reviewed recently elsewhere.[1f] Also their potential as efficient mimetics for selenoenzymes will not be discussed. [2] In this Highlight we will focus on the catalytic use of selenium electrophiles for selenenylations and halogenations as well as the use of perseleninic acids as catalytic oxidants for various substrates.The use of electrophilic selenium reagents is a very versatile strategy for functionalizing alkenes 1. To avoid the use of stoichiometric amounts of selenium reagents, researchers have sought for analogous catalytic methods. Selenenylation-deselenenylation sequences involve two steps: the initial selenofunctionalization is followed by oxidation of the organoselenium moiety in 2, which allows the regeneration of the reagent through b elimination giving 3 or substitution to provide 4 (Scheme 1). Various reagents can be used to activate the selenide moiety in 2 to undergo elimination or substitution. The most explored approach involves oxidation with an excess of persulfate.[3] The oxidant is initially responsible for the generation of the electrophilic selenenylating agent from the corresponding diselenide and then for the oxidation of the selenium moiety in 2 allowing the regeneration of the catalyst. This approach proved to be useful for functionalizations such as hydroxylations, alkoxylations, and cyclizations, and when chiral nonracemic diselenides were used, interesting levels of stereoselectivity were reached. [3] Depending on the substrate 5, either an addition-elimination sequence to yield 6 or a cyclization-elimination sequence to give 7 is possible by using an electrochemical procedure (Scheme 2).[4] The reaction is initiated by anodic oxidation of bromide to bromine. The latter reacts with the diselenide to afford the arylselenenyl bromide, which promotes the selenofunctionalization. Subsequent elimination of the selenium moiety via a tetravalent selenium compound gives the products 6 or 7 and regenerates the arylselenenyl bromide. Alternatively, hypervalent iodine reagents such as [bis(trifluoroacetoxy)iodo]benzene can be used as oxidants, in combination with catalytic amounts (5 mol %) of diselenides, to effect the conversion of butenoic acids 5 (R = H) to the corresponding butenolides 7 in yields of up to 95 %.[5] In a diselenide-catalyzed dihydroxylation of alkenes with ammonium persulfate as the oxidant both nucleophiles are hydroxy groups and diols of type 4 (Nu = Nu' =...

Selenium (Se) is an important micronutrient for living organisms, since it is involved in several physiological and metabolic processes. Se intake in humans is often low and very seldom excessive, and its bioavailability depends also on its chemical form, with organic Se as the most available after ingestion. The main dietary source of Se for humans is represented by plants, since many species are able to metabolize and accumulate organic Se in edible parts to be consumed directly (leaves, flowers, fruits, seeds, and sprouts) or after processing (oil, wine, etc.). Countless studies have recently investigated the Se biofortification of plants to produce Se-enriched foods and elicit the production of secondary metabolites, which may benefit human health when incorporated into the diet. Moreover, feeding animals Se-rich diets may provide Se-enriched meat. This work reviews the most recent literature on the nutraceutical profile of Se-enriched foods from plant and animal sources.

The interest in the synthesis of Se-containing compounds is growing with the discovery of derivatives exhibiting various biological activities. In this manuscript, we have identified a series of 2,2'-diselenobisbenzamides (DISeBAs) as novel HIV retroviral nucleocapsid protein 7 (NCp7) inhibitors. Because of its pleiotropic functions in the whole viral life cycle and its mutation intolerant nature, NCp7 represents a target of great interest which is not reached by any anti-HIV agent in clinical use. Using the diselenobisbenzoic scaffold, amino acid, and benzenesulfonamide derivatives were prepared and biologically profiled against different models of HIV infection. The incorporation of amino acids such as glycine and glutamate into DISeBAs 7 and 8 resulted in selective anti-HIV activity against both acutely and chronically infected cells as well as an interesting virucidal effect. DISeBAs demonstrated broad antiretroviral activity, encompassing HIV-1 drug-resistant strains including clinical isolates, as well as simian immunodeficiency virus (SIV). Time of addition experiments, along with the observed dose dependent inhibition of the Gag precursor proper processing, confirmed that their mechanism of action is based on NCp7 inhibition.