Organofluorine Compounds in Biology and Medicine

Chapter 1. General Aspects of Organofluorine Compounds

• 1. Introduction
• 2. C–F Bond Strengths
• 3. Effect of the Neighboring C–F Bonds on the C–H Bond Dissociation Energies
• 4. Effect of Fluorine on the Acidity and Basicity
• 5. Effect of Fluorine on the Metabolic Stability
• 6. Effect of Fluorine on the Bioavailability
• 7. Positron Emission Tomography Tracers
• 8. ¹⁹F NMR Spectroscopic Techniques for Probing Biochemical Mechanisms
• 9. Summary and Outlook

Chapter 2. Fluorinated Compounds in Enzyme-Catalyzed Reactions

• 1. Introduction
• 2. Bacterial Metabolism of the Fluoroacetate
• 3. Biosynthesis of Fluoroacetate and Fluorothreonine
• 4. Enzymatic Defluorination
• 5. Mechanism-Based Enzyme Inhibitors
• 6. Reversible Inhibitors
• 7. Summary and Outlook

Chapter 3. Synthetic Methods

• 1. Introduction
• 2. Fluorination by Elemental Fluorine
• 3. Hydrogen Fluoride and Its Amine Complexes
• 4. Selective ortho-Fluorination of Pyridines by AgF₂
• 5. Deoxyfluorinations by DAST and Related Reagents
• 6. Dediazoniation–Fluorination of Amines
• 7. gem-Difluorinations
• 8. Trifluoromethylations
• 9. Pentafluorosulfanyl Compounds
• 10. Summary and Outlook

Chapter 4. Fluorinated Amino Acids, Peptides, and Proteins

• 1. Introduction
• 2. Fluorinated Leucine
• 3. Fluorinated Proline and its Effect on Collagen
• 4. Fluorinated Methionines
• 5. Fluorinated Tyrosines
• 6. Fluorinated Phenylalanine
• 7. Peptide Mimetics in Drug Discovery
• 8. Summary and Outlook

Chapter 5. Organofluorine Pharmaceuticals

• 1. Introduction
• 2. Pharmaceuticals with gem-Difluoromethylene and Trifluoromethyl Moieties
• 3. Antibacterials
• 4. Antimalarials
• 5. Antidiabetics
• 6. Nonsteroidal Antiinflammatory Drugs
• 7. Corticosteroids
• 8. Antiviral Drugs
• 9. Antidepressant Drugs
• 10. Antihypercholesterolemia Drugs
• 11. Anticoagulating (Blood-Thinning) Agents
• 12. Summary and Outlook

Chapter 6. Organofluorine Anesthetics

• 1. Introduction
• 2. Mechanism of Action of Inhalation Anesthetics
• 3. Chiral Anesthetics
• 4. Environmental Impact of Fluorinated Anesthetics
• 5. Synthesis and Toxicity of Fluorinated Anesthetics
• 6. Summary and Outlook

Chapter 7. Organofluorine Compounds as Positron Emission Tomography Tracers

• 1. Introduction
• 2. ¹⁸F-Labeled Pharmaceuticals
• 3. Synthesis of ¹⁸F-labeled Compounds
• 4. ¹⁸F-Labeled Neurotransmitters
• 5. [¹⁸F]Corticosteroids
• 6. ¹⁸F-Labeled Nucleosides
• 7. ¹⁸F-Radiolabeling of Peptides and Proteins
• 8. Enzymatic Synthesis of ¹⁸F-PET tracers
• 9. Summary and Outlook

Chapter 8. Organofluorine Compounds in Neurological Disorders

• 1. Introduction
• 2. BACE-1 Inhibitors
• 3. GSMS and γ-secretase Inhibitors
• 4. Cell Cycle Inhibitors
• 5. Antiinflammatory Compounds as Therapeutics of AD
• 6. Summary and Outlook

Chapter 9. Organofluorine Compounds as Anticancer Agents

• 1. Introduction
• 2. Nucleoside-Based Therapeutics
• 3. Receptor Tyrosine Kinase Inhibitors
• 4. Capecitabine and Lapatinib
• 5. Trametinib and Dabrafenib
• 6. Paclitaxel and Related Taxoids
• 7. Bicalutamide
• 8. Vemurafenib
• 9. Sonidegib
• 10. Ponatinib
• 11. Faslodex
• 12. Vinflunine
• 13. Summary and Outlook