Synthesis of Biologically Relevant Small Molecules Containing Selenium. Part A. Antioxidant Compounds

Abstract

The design and synthesis of organoselenium compound as bioactive structures have achieved a new dimension since the 1970s, when many reports described the identification of various selenoproteins, which are involved in a wide variety of biological processes, including antioxidant defense, thyroid hormone production and immune response. In this chapter, strategies and methods for the preparation of synthetic antioxidants containing selenium are reviewed. The unique redox properties of selenium confer catalytic activity to organoselenium compounds and influence their biological properties as well as the methods selected for their preparation. Several approaches can be applied in order to obtain organoselenium compounds, such as reaction of elemental selenium or diselenides with different types of carbanions or reaction of organic electrophiles with selenolate anions generated by different methods, as discussed herein.

Copper-Catalyzed Synthesis of Unsymmetrical Diorganyl Chalcogenides (Te/Se/S) from Boronic Acids under Solvent-Free Conditions

“…In addition, catalytic transformations have been widely applied in organochalcogen chemistry for the preparation of diorganyl-tellurides, -selenides and -sulfides, which are interesting target molecules and valuable synthetic intermediates for several transformations in modern organic synthesis [ 8 , 9 , 10 ]. Besides the synthetic applications, these types of molecules have shown relevant biological properties, such as antitumor, antioxidant, antiviral, antimicrobial and neuroprotective effects [ 11 , 12 , 13 , 14 , 15 , 16 , 17 , 18 , 19 ]. Organochalcogen compounds also have noteworthy applications in materials science [ 20 , 21 , 22 ].…”

Synthesis and Biological Evaluation of 2-Picolylamide-Based Diselenides with Non-Bonded Interactions

“…Among them, selenium-containing compounds have been successfully employed in certain reactions [8] as catalysts [9], ionic liquids [10], and intermediates in total synthesis [3,4,5,6,7,11]. In this context, the formation of C-Se bonds has contributed to the access to a wide range of biologically active molecules [12,13,14] and functional materials [15].…”

“…X-ray crystallography [22,23,24], 77 Se NMR [23,24,25] and modern computational methods [26,27] have been used to explore and provide insights into these possible nonbonding interactions. There are many examples available where organoselenium compounds, e.g., 2 – 3 (Figure 1) [28,29] with proximal interaction showed significant biological activities in comparison to ebselen ( 1 ; a mimic of GPx that also reacts with peroxynitrite) [5,12].…”

Synthesis of Functionalized Organoselenium Materials: Selenides and Diselenides Containing Cholesterol

“…[1,2] Additionally, diorganodiselenides, the selenium counterpart of organic peroxides, play an important role in organochalcogen chemistry, because they are stable, easy to handle, and sufficiently reactive to produce electrophilic, nucleophilic, and radical species. [5][6][7][8] In addition, it has been shown that the presence of different chalcogen atoms in organic compounds can induce changes in their photophysical properties. [5][6][7][8] In addition, it has been shown that the presence of different chalcogen atoms in organic compounds can induce changes in their photophysical properties.…”

“…[3,4] The design of new organoselenium compounds, along with other developments, is attracting considerable attention, particularly because of their ability to mimic natural compounds with important biological properties, such as antioxidant, antitumor, antimicrobial, and antiviral activity. [5][6][7][8] In addition, it has been shown that the presence of different chalcogen atoms in organic compounds can induce changes in their photophysical properties. [9,10] Moreover, the photophysical properties allied with their liquid crystalline character mean that such materials are promising for optical device applications, such as emissive LC displays, polarized organic lasers, and anisotropic OLEDs.…”