Begue J.-P., Bonnet-Delpon D. Bioorganic and medicinal chemistry of fluorine

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Wiley, 2008, 365 c., ISBN 978-0-470-27830-7 (cloth)

CONTENTS

Foreword
Preface to the English Edition

General Remarks on Structural, Physical, and Chemical Properties of Fluorinated Compounds
Structural Effects
Physical Properties
Effects on Electronic Properties and Reactivity

Overview on the Preparation of Fluorinated Compounds
Preparation of Monofluorinated Compounds
Preparation of Difluorinated Compounds
Preparation of Trifluoromethyl Compounds
Synthesis of Perfluoroalkyl Compounds

Effects of Fluorine Substitution on Biological Properties
Affinity for the Macromolecule Target
Absorption
Metabolism
Modification of Chemical Reactivity: Enzyme Inhibitors

Fluorinated Analogues of Natural Products
Fluorinated Products in Nature
Steroids
Terpenes
Pigments and Vitamins
Lipids and Prostanoids
Pheromones and Toxins
Alkaloids
Anthracyclines

Fluorinated Derivatives of a-Amino Acids and Proteins
Fluorinated Aliphatic Amino Acids
Aromatic Amino Acids: Phenylalanine, Tyrosine, Histidine, and Tryptophan
Functional Fluorinated Amino Acids
Fluoroalkyl Amino Acids
Incorporation of Fluorinated Amino Acids into Peptides and Proteins

Saccharidic Fluorinated Derivatives
Glycosyl Fluorides
Mono- and Difluorinated Analogues of Sugars
Fluoromethyl Derivatives of Sugars
Perfluoroalkylated Sugars

Inhibition of Enzymes by Fluorinated Compounds
Substrate Analogues
Destabilization of Reaction Intermediates (or of Transition States) of Enzymatic Processes by Fluorinated Groups
Inhibitors that are Analogues of the Transition State: Di- and Trifluoromethyl Ketones
Mechanism-Based Inhibitors
Fluorinated Inhibitors Involving a Still Unknown Mechanism

Fluorinated Drugs
Antitumor and Antiviral Fluorinated Drugs
Anti-infectious Drugs
Drugs for CNS Disorders
Drugs of Inflammatory and Immunity Disorders
Drugs for Cardiovascular Disorders
Drugs for Gastrointestinal Disorders
Drugs for Endocrine and Metabolic Disorders
Miscellaneous
Highly Fluorinated Compounds with Clinical Uses
Fluorinated Functions and Motifs in Medicinal Chemistry

Appendix: INN and Trademark Names
References

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