Tailor‐Made Amino Acids and Fluorinated Motifs as Prominent Traits in Modern Pharmaceuticals

• Published in: Chemistry : a European journal 2020-09, Vol.26 (50), p.11349-11390
• Main Authors: Mei, Haibo, Han, Jianlin, White, Sarah, Graham, Daniel J., Izawa, Kunisuke, Sato, Tatsunori, Fustero, Santos, Meanwell, Nicholas A., Soloshonok, Vadim A.
• Format: Article
• Language: English
• Subjects: Amino Acids; Biological properties; cancer; Chemical synthesis; Chemistry; Chemistry, Pharmaceutical; drug discovery; Exploitation; Fluorination; fluorine substitution; fluorine-containing drugs; Humans; Hydrocarbons, Fluorinated; Pharmaceutical Preparations; Pharmaceuticals; Structural analysis
• ISSN: 0947-6539; 1521-3765
• DOI: 10.1002/chem.202000617

Structural analysis of modern pharmaceutical practices allows for the identification of two rapidly growing trends: the introduction of tailor‐made amino acids and the exploitation of fluorinated motifs. Curiously, the former represents one of the most ubiquitous classes of naturally occurring compounds, whereas the latter is the most xenobiotic and comprised virtually entirely of man‐made derivatives. Herein, 39 selected compounds, featuring both of these traits in the same molecule, are profiled. The total synthesis, source of the corresponding amino acids and fluorinated residues, and medicinal chemistry aspects and biological properties of the molecules are discussed. Designed to fit: This review profiles 39 selected bioactive compounds that feature tailor‐made amino acid residues and fluorinated motifs developed in modern pharmaceuticals. The total synthesis, brief medicinal chemistry, and biological properties of these selected examples are discussed.