Bioorganic and Medicinal Chemistry of Fluorine

Jean-Pierre Bégué 지음

Wiley-Interscience 2008년 06월 02일 출간

작품소개

책소개

Provides a thorough overview of the role of fluorine in pharmaceutical science and development Includes chapters on fluorinated analogues of natural products, fluorinated amino acids and peptides, and derivatives of sugars Classifies marketed and in-development fluorinated pharmaceuticals according to their therapeutic classes

목차

Foreword.Preface to the English Edition1 General Remarks on Structural, Physical, and Chemical Properties of Fluorinated Compounds.1.1 Structural Effects.1.2 Physical Properties.1.2.1 Boiling Point.1.2.2 Surface Tension and Activity.1.2.3 Polarity-Solubility.1.2.4 Lipophilicity.1.3 Effects on Electronic Properties and Reactivity.1.3.1 Effects of Fluorination on Bond Energies and Reactivity.1.3.2 Effects of Fluorination on the Electronic Repartition of a Molecule.1.3.3 Acidity, Basicity, and Hydrogen Bond.1.3.4 Steric Effects.1.3.5 Fluorination Effects on the Stability of Reaction Intermediates (Carbocations, Carbanions, and Radicals).References.2 Overview on the Preparation of Fluorinated Compounds.2.1 Preparation of Monofluorinated Compounds.2.1.1 Nucleophilic Fluorination.2.1.2 Electrophilic Fluorination.2.1.3 Formation of Carbon&~Carbon Bonds Starting from Monofluorinated Synthons.2.2 Preparation of Difluorinated Compounds.2.2.1 Nucleophilic Fluorination.2.2.2 Electrophilic Fluorination.2.2.3 Starting from Di- and Trifluoromethyl Compounds.2.3 Preparation of Trifluoromethyl Compounds.2.3.1 Fluorination.2.3.2 Nucleophilic Trifluoromethylation.2.3.3 Electrophilic Trifluoromethylation.2.3.4 Radical Trifluoromethylation.2.3.5 Metal-Catalyzed Trifluoromethylation.2.3.6 Formation of Carbon&~Carbon Bonds from Trifluoromethyl Compounds.2.4 Synthesis of Perfluoroalkyl Compounds.References.3 Effects of Fluorine Substitution on Biological Properties.3.1 Affinity for the Macromolecule Target.3.1.1 Steric Effects.3.1.2 Conformational Changes.3.1.3 Dipolar Interactions and Electric Field.3.1.4 Hydrogen Bonds and Other Weak Interactions.3.1.5 pKa of Amines.3.1.6 Fluorous Interactions.3.2 Absorption.3.2.1 Lipophilicity.3.2.2 pKa and Solubility.3.3 Metabolism.3.3.1 Oxidative Metabolism.3.3.2 Hydrolytic Metabolism.3.4 Modificatio

출판사 서평

"This is an excellent book for those contemplating incorporation of fluorine into their drug design research investigations and how it can be accomplished. It is also an excellent reference book for experts in the area. I enthusiastically recommend adding this to both individual and library collections." (Journal of Medicinal Chemistry, December 25, 2008)"The book is clearly written and has been adequately translated … .Its compact size, and abundance of helpful schemes, figures, tables and structures make it convenient aid for the practicing scientist." (Journal of the American Chemical Society, December 31, 2008)"I am pleased to recommend Bioorganic and Medicinal Chemistry of Fluorine as an invaluable reference source and stimulus to further research, for pharmaceutical and medicinal chemists, organic chemists, and biochemists in academia and industry, and for advanced students and instructors in these fields." (Angewandte Chemie, October 13, 2008)

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저자(글) Jean-Pierre Bégué

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Jean-Pierre Begue, PHD, is Emeritus Director of Research at the Centre National de la recherche Scientifique (CNRS) in France. Dani#232;le Bonnet-Delpon, PHD, is Director of Research at CNRS. The authors and their coworkers have developed the chemistry of fluorinated compounds, from organic synthesis to medicinal chemistry.