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| Foreword | |
| Preface to the English Edition | |
| General Remarks on Structural, Physical, and Chemical Properties of Fluorinated Compounds | |
| Structural Effects | |
| Physical Properties | |
| Boiling Point | |
| Surface Tension and Activity | |
| Polarity-Solubility | |
| Lipophilicity | |
| Effects on Electronic Properties and Reactivity | |
| Effects of Fluorination on Bond Energies and Reactivity | |
| Effects of Fluorination on the Electronic Repartition of a Molecule | |
| Acidity, Basicity, and Hydrogen Bond | |
| Steric Effects | |
| Fluorination Effects on the Stability of Reaction Intermediates (Carbocations, Carbanions, and Radicals) | |
| References | |
| Overview on the Preparation of Fluorinated Compounds | |
| Preparation of Monofluorinated Compounds | |
| Nucleophilic Fluorination | |
| Electrophilic Fluorination | |
| Formation of CarbonûCarbon Bonds Starting from Monofluorinated Synthons | |
| Preparation of Difluorinated Compounds | |
| Nucleophilic Fluorination | |
| Electrophilic Fluorination | |
| Starting from Di- and Trifluoromethyl Compounds | |
| Preparation of Trifluoromethyl Compounds | |
| Fluorination | |
| Nucleophilic Trifluoromethylation | |
| Electrophilic Trifluoromethylation | |
| Radical Trifluoromethylation | |
| Metal-Catalyzed Trifluoromethylation | |
| Formation of CarbonûCarbon Bonds from Trifluoromethyl Compounds | |
| Synthesis of Perfluoroalkyl Compounds | |
| References | |
| Effects of Fluorine Substitution on Biological Properties | |
| Affinity for the Macromolecule Target | |
| Steric Effects | |
| Conformational Changes | |
| Dipolar Interactions and Electric Field | |
| Hydrogen Bonds and Other Weak Interactions | |
| pKa of Amines | |
| Fluorous Interactions | |
| Absorption | |
| Lipophilicity | |
| pKa and Solubility | |
| Metabolism | |
| Oxidative Metabolism | |
| Hydrolytic Metabolism | |
| Modification of Chemical Reactivity: Enzyme Inhibitors | |
| Analogue of Substrates as Inhibitors | |
| Inhibition by Stabilization or Destabilization of Intermediates of Biological Processes | |
| Irreversible Inhibition with Mechanism-Based Inhibitors (Suicide Substrates) | |
| References | |
| Fluorinated Analogues of Natural Products | |
| Fluorinated Products in Nature | |
| Steroids | |
| Corticosteroids | |
| Steroids with Trifluoromethyl Groups in Angular Position | |
| Fluorinated Analogues of Metabolites of Vitamin D3 | |
| Other Fluorinated Steroids | |
| Terpenes | |
| Artemisinin | |
| Taxol | |
| Pigments and Vitamins | |
| Retinoids | |
| Carotenoids | |
| Vitamin D | |
| Vitamins E and K | |
| Porphyrins | |
| Lipids and Prostanoids | |
| Pheromones and Toxins | |
| Vinca Alkaloids | |
| Cinchona Alkaloids | |
| Camptothecin | |
| Other Fluorinated Alkaloids | |
| Macrolides | |
| Epothilone | |
| Erythromycin | |
| Amphotericin B | |
| Avermectin | |
| Anthracyclines | |
| References | |
| Fluorinated Derivatives of a-Amino Acids and Proteins | |
| Fluorinated Aliphatic Amino Acids | |
| Alanines | |
| Valines, Leucines, and Isoleucines | |
| Prolines | |
| Aromatic Amino Acids: Phenylalanine, Tyrosine, Histidine, and Tryptophan | |
| Functional Fluorinated Amino Acids | |
| Serines and Threonines | |
| Aspartic Acids and Arginines | |
| Glutamic Acids and Glutamines | |
| Lysine, Ornithine, and Arginine | |
| Cysteines and Methionines | |
| Fluoroalkyl Amino Acids | |
| Mono- and Difluoromethyl Amino Acids | |
| Trifluoromethyl Amino Acids | |
| Incorporation of Fluorinated Amino Acids into Peptides and Proteins | |
| Polypeptides | |
| Proteins | |
| References | |
| Saccharidic Fluorinated Derivatives | |
| Glycosyl Fluorides | |
| Mono- and Difluorinated Analogues of Sugars | |
| Fluorinated Furanoses and Nucleosides | |
| Fluorinated Pyranoses | |
| Fluoromethyl Derivatives of Sugars | |
| Difluorovinyl Compounds | |
| Difluoromethylene-C-Glycosides | |
| C-Difluoromethyl Glycosides | |
| Trifluoromethylated Sugars | |
| Preparation of C-Perfluoroalkyl Sugars | |
| O- and S-Fluoroalkyl Glycosides | |
| Applications of Amphiphilic Fluoroalkyl Sugars | |
| References | |
| Inhibition of Enzymes by Fluorinated Compounds | |
| Substrate Analogues | |
| Fluorine Replaces a Hydrogen Involved in the Catalytic Cycle | |
| Fluorine Replaces a Hydroxyl | |
| Fluorinated Analogues of Substrates in Which Fluorine is Not Directly Involved in the Inhibition. | |
| Destabilization of Reaction Intermediates (or of Transition States) of Enzymatic Processes by Fluorinated Groups | |
| Prenyl Transfer | |
| Inhibition of Glycosidases and Glycosyltransferases | |
| Inhibition of UDP-GlcNAC Enolpyruvyltransferase (MurZ) | |
| Enolpyruvate Shikimate Phosphate Synthase (EPSPS) | |
| Inhibitors that are Analogues of the Transition State: Di- and Trifluoromethyl Ketones | |
| Serine Enzymes | |
| Inhibition of Aspartyl Enzymes | |
| Inhibition of Metalloproteases | |
| Cysteine Protease and Thiol Enzymes | |
| Mechanism-Based Inhibitors | |
| Inhibition of Pyridoxal Phosphate Enzymes | |
| Thymidylate Synthase | |
| Inhibition of Monoamine Oxidases | |
| D-Ala-D-Ala Dipeptidase (VanX) | |
| Inhibition of Ribonucleotide Diphosphate Reductase | |
| Inhibition of S-Adenosylhomocysteine Hydrolase | |
| Inhibition of Cytidine-50-diphosphate-D-Glucose 4,6-Dehydratase (CDP D-Glucose 4,6-Dehydratase) | |
| Other Irreversible Inhibitors | |
| Fluorinated Inhibitors Involving a Still Unknown Mechanism | |
| Inhibition of the Steroid C17(20)lyase | |
| Phosphatidylinositol Phospholipase C (PI-PLC) | |
| Inhibition of the Protein of Transfer of Cholesteryl Esters | |
| Fluoropolyamines as Inhibitors of the Biosynthesis of Polyamines | |
| Inhibition of the Biosynthesis of Cholesterol | |
| References | |
| Fluorinated Drugs | |
| Antitumor and Antiviral Fluorinated Drugs | |
| Anti-infectious Drugs | |
| Fluorinated Antibiotic Drugs | |
| Antifungal Drugs | |
| Fluorinated Drugs for Parasitic Diseases | |
| Drugs for CNS Disorders | |
| Neuroleptics | |
| Drugs for Depressive Disorders | |
| Anxiolytics and Sedatives | |
| Other Drugs for CNS Disorders | |
| Drugs of Inflammatory and Immunity Disorders | |
| Fluorocorticosteroids | |
| H1 Antagonist Antiallergics | |
| Drugs for Asthma and Respiratory Disorders | |
| Analgesic and Antiarthritic Drugs | |
| Drugs for Cardiovascular Disorders | |
| Drugs for Gastrointestinal Disorders | |
| Prevention and Treatment of Ulcer | |
| Antiemetic Agents | |
| Drugs for Bowel Disorders | |
| Drugs for Endocrine and Metabolic Disorders | |
| Drugs Acting on Steroid Hormone Receptors | |
| Drugs for Benign Prostatic Hypertrophy (BPH) | |
| Drugs for Other Urologic Disorders | |
| Drugs for Calcemia Disorders | |
| Drugs for Diabetes | |
| Drugs for Hepatic Disorders | |
| Miscellaneous | |
| Drugs for Ophthalmic Disorders | |
| Drugs for Genetic Disease | |
| Contrast and Diagnostic Agents | |
| Highly Fluorinated Compounds with Clinical Uses | |
| General Anesthetics | |
| Therapeutic Uses of Perfluorocarbons | |
| Fluorinated Functions and Motifs in Medicinal Chemistry | |
| Fluorinated Ethers | |
| Fluorinated Alcohols and Amines | |
| Fluorinated Ketones | |
| Fluoroalkyl Groups | |
| Appendix: INN and Trademark Names | |
| References | |
| Index | |
| Table of Contents provided by Publisher. All Rights Reserved. |
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