Organofluorine Compounds in Biology and Medicine

This book covers topics on biochemically relevant organofluorine compounds and their synthesis and biochemical pathways. Organofluorine compounds have renewed interest in pharmaceutical industry, and therefore a concise book on this topic is highly relevant to the scientific community involved in this area.

• Covers the synthesis, biochemical, and therapeutic applications of organofluorine compounds
• Offers a complete text on biochemically relevant organofluorine compounds and their synthesis and mechanistic pathways
• Provides one of the first major reference books on the biological and medicinal applications of organofluorine chemistry

This book suits a wide audience, including chemists, organic chemists, physical organic chemists, synthetic chemists, medicinal and pharmaceutical chemists, organometallic chemists, medicinal chemists, biologists, and graduate and post graduate students.

• Dedication
• Short Biography
• Preface
• Importance of this Book
• 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
• Index