SnAP reagents for the synthesis of selenomorpholines and 1,4-selenazepanes and their biological evaluation

β-Seleno-α-amino acids, known as selenocysteine (Sec) derivatives, have emerged as important targets because of their role in chemical biology, not only as part of selenoproteins with important redox properties, but also because of their activities as antivirals or metabolites effective in inhibiting carcinogenesis. In addition, there is a demand for this type of compounds due to their use in native chemical ligation to construct large peptides. Therefore, this review summarizes the various synthetic methods that have been published to construct Sec derivatives. Most of them involve the generation of the C-Se bond by nucleophilic substitution reactions, but other reactions such as radical or multicomponent strategies are also reported. Of particular importance is the Se-Michael addition of Se-nucleophiles to chiral bicyclic dehydroalanines, in which the stereogenic centre is generated under complete stereocontrol. 1 Introduction 2 Previously reviewed synthesis of Sec 3 Retrosynthesis of Sec derivatives 4 Sec derivatives by nucleophilic substitutions 5 Sec derivatives by radical processes 6 Sec derivatives by 1,4-conjugate additions

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SnAP reagents for the synthesis of selenomorpholines and 1,4-selenazepanes and their biological evaluation

Abstract: We report the first set of selenium-containing SnAP reagents for the direct synthesis of C-substituted selenomorpholines and 1,4-selenazepanes and the biological evaluation of these elusive N-heterocycles.

Cited by 3 publications

References 31 publications

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