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Chalcogen OCF3-isosteres Modulate Drug Properties without Introducing Inherent Liabilities

Tlili, Anis and Ghiazza, Clement and Thierry, Billard (2019) Chalcogen OCF3-isosteres Modulate Drug Properties without Introducing Inherent Liabilities. ChemMedChem : chemistry enabling drug discovery, 14 (17). pp. 1586-1589. ISSN 1860-71791860-7187

Abstract

The synthesis of SCF3 as well as SeCF3 isosteres of two OCF3–containing drugs was achieved through visible light and copper-catalyzed processes. Herein, we show that chalcogen replacement modulates physico-chemical and ADME properties without introducing intrinsic liabilities. The S- and SeCF3 groups are more lipophilic as their O-parent; however, microsomal stability is unchanged, indicating that these molecular changes may be beneficial for in vivo half-life. Enabled by modern synthetic methods, we present the chalcogen-CF3 groups as potential key players for future fluorinated pharmaceuticals.

Item Type: Article
Date Deposited: 22 Oct 2019 00:45
Last Modified: 22 Oct 2019 00:45
URI: https://oak.novartis.com/id/eprint/39842

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