Abstract
In the last decades, organoselenium compounds gained interest due to their important biological features. However, the lack of solubility, which characterizes most of them, makes their actual clinical exploitability a hard to reach goal. Selenosugars, with their intrinsic polarity, do not suffer from this issue and as a result, they can be conceived as a useful alternative. The aim of this review is to provide basic knowledge of the synthetic aspects of selenosugars, selenonium salts, selenoglycosides, and selenonucleotides. Their biological properties will be briefly detailed. Of course, it will not be a comprehensive dissertation but an analysis of what the authors think is the cream of the crop of this interesting research topic.
Highlights
Organoselenium compounds are gaining interest in the medicinal chemistry community due to their promising biological activities for a wide range of clinical applications [1,2,3,4,5,6,7]
The selenosugars and the selenosugar-containing classes of compounds were analyzed in order to give fruitful insights to those interested in this research field or who are just approaching it
SeTal, compound 20, is a clear example of an organoselenium compound endowed with antioxidant activity in vitro and in vivo thanks to its water-solubility, which makes it
Summary
Organoselenium compounds are gaining interest in the medicinal chemistry community due to their promising biological activities for a wide range of clinical applications [1,2,3,4,5,6,7]. Its treatment with an ethanolic solution of Na2Se and the successive acidic deprotection gave. Compounds 17 and 18 were efficiently obtained starting from D-mannose, which was firstly regioselectively protected and reduced, giving the diol 24, that was successively activated by bismesylation for the subsequent selenium nucleophilic substitution, affording 17 after deprotection using TFA (Scheme 4). The keto moiety was stereoselectively converted into the key alcohol by employing the Luche-type reductive conditions, and activated as mesylate in compound 27. Its treatment with an ethanolic solution of Na2Se and the successive acidic deprotection gave the target selenosugar 18 [28]. Compound 31 was converted into the prot5ecotfe2d7 selenosugar and deprotected by treatment with trifluoroacetic acid in dichloromethane [29]
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