Synthesis of Biologically Relevant Small Molecules Containing Selenium. Part B. Anti‐infective and Anticancer Compounds

Abstract

In the 19705 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. This brought a new dimension to the design and synthesis of organoselenium compounds as bioactive structures. In this chapter, strategies and methods for the preparation of anti‐infective, chemopreventive as well as anticancer compounds are reviewed. The unique redox properties of selenium confer catalytic activity to organoselenium compounds and influence their biological propert ies 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 carbon nucleophiles or reaction of organic electrophiles with selenolate anions generated by different methods, as discussed herein.

Natural Compounds and Their Structural Analogs in Regio- and Stereoselective Synthesis of New Families of Water-Soluble 2H,3H-[1,3]thia- and -Selenazolo[3,2-a]pyridin-4-ium Heterocycles by Annulation Reactions

“…Selenium analogs, [1,3]selenazolo [3,2-a]pyridinium derivatives are less studied. Selenium-containing heterocycles [9][10][11][12][13] represent an important family of compounds exhibiting various types of biological activity including anti-inflammatory, antitumor, antifungal, and glutathione peroxidase-like action [12][13][14][15][16][17][18][19][20]. The selenium-containing heterocyclic drug ebselen is [9][10][11][12][13] represent an important family of compounds exhibiting various types of biological activity including anti-inflammatory, antitumor, antifungal, and glutathione peroxidase-like action [12][13][14][15][16][17][18][19][20].…”

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].…”