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      Direct Catalytic Trifluoromethylthiolation of Boronic Acids and Alkynes Employing Electrophilic Shelf-StableN-(trifluoromethylthio)phthalimide

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      Angewandte Chemie International Edition
      Wiley-Blackwell

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          Fluorine in medicinal chemistry.

          It has become evident that fluorinated compounds have a remarkable record in medicinal chemistry and will play a continuing role in providing lead compounds for therapeutic applications. This tutorial review provides a sampling of renowned fluorinated drugs and their mode of action with a discussion clarifying the role and impact of fluorine substitution on drug potency.
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            Fluorine in pharmaceuticals: looking beyond intuition.

            Fluorine substituents have become a widespread and important drug component, their introduction facilitated by the development of safe and selective fluorinating agents. Organofluorine affects nearly all physical and adsorption, distribution, metabolism, and excretion properties of a lead compound. Its inductive effects are relatively well understood, enhancing bioavailability, for example, by reducing the basicity of neighboring amines. In contrast, exploration of the specific influence of carbon-fluorine single bonds on docking interactions, whether through direct contact with the protein or through stereoelectronic effects on molecular conformation of the drug, has only recently begun. Here, we review experimental progress in this vein and add complementary analysis based on comprehensive searches in the Cambridge Structural Database and the Protein Data Bank.
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              A survey of Hammett substituent constants and resonance and field parameters

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                Author and article information

                Journal
                Angewandte Chemie International Edition
                Angew. Chem. Int. Ed.
                Wiley-Blackwell
                14337851
                February 03 2014
                February 03 2014
                : 53
                : 6
                : 1650-1653
                Article
                10.1002/anie.201307484
                550050de-e98d-4f1a-97ac-a815172dde14
                © 2014

                http://doi.wiley.com/10.1002/tdm_license_1.1

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