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Ojima I. (ed.) Fluorine in Medicinal Chemistry and Chemical Biology

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Ojima I. (ed.) Fluorine in Medicinal Chemistry and Chemical Biology
Blackwell Publishing, Ltd. 2009. - 624
This book presents the recent developments and future prospects of fluorine in medicinal chemistry and chemical biology. The extraordinary potential of fl uorine - containing biologically relevant molecules in peptide/protein chemistry, medicinal chemistry, chemical biology, pharmacology, and drug discovery as well as diagnostic and therapeutic applications, was recognized by researchers who are not in the traditional fl uorine chemistry fi eld, and thus the new wave of fl uorine chemistry has been rapidly expanding its biomedical frontiers.
The book starts with an introductory chapter, summarizing and discussing the unique properties of fluorine and their relevance to medicinal chemistry and chemical biology. Then, several hot topics in medicinal chemistry as well as discovery and development of fluorine - containing drugs and drug candidates are described, including fl uorinated prostanoids (for glaucoma), fluorinated conformationally restricted glutamate analogues (for CNS disorder), fl uorinated MMP inhibitors (e.g. for cancer metastasis intervention), fluoro - taxoids (for cancer), trifluoro - artemisinin (for malaria), and fl uorinated nucleosides (for viral infections).
This book will serve as an excellent reference book for graduate students as well as scientists at all levels in both academic and industrial laboratories.
Contents
Preface page
List of Contributors
Abbreviations
Introduction: Basic Aspects of Fluorine in Chemistry and Biology
Unique Properties of Fluorine and Their Relevance to Medicinal Chemistry and Chemical Biology

Takashi Yamazaki, Takeo Taguchi, and Iwao Ojima
Medicinal Chemistry
Fluorinated Prostanoids: Development of Tafl uprost, a New Anti-glaucoma Agent

Yasushi Matsumura
Fluorinated Conformationally Restricted Glutamate Analogues for CNS Drug Discovery and Development
Atsuro Nakazato
Fluorinated Inhibitors of Matrix Metalloproteinases
Roberta Sinisi, Monika Jagodzinska, Gabriele Candiani, Florent Huguenot, Monica Sani, Alessandro Volonterio, Raffaella Maffezzoni, and Matteo Zanda
Fluoro-Taxoid Anticancer Agents
Antonella Pepe, Larisa Kuznetsova, Liang Sun, and Iwao Ojima
Antimalarial Fluoroartemisinins: Increased Metabolic and Chemical Stability
Jean-Pierre Bégué and Danièle Bonnet-Delpon
Synthesis and Biological Activity of Fluorinated Nucleosides
Tokumi Maruyama, Masahiro Ikejiri, Kunisuke Izawa, and Tomoyuki Onishi
Synthetic Methods for Medicinal Chemistry and Chemical Biology
Synthesis of gem-Difl uoromethylenated Nucleosides via gem-Difl uoromethylene-containing Building Blocks

Wei-Dong Meng and Feng-Ling Qing
Recent Advances in the Syntheses of Fluorinated Amino Acids
Kenji Uneyama
Fluorinated Moieties for Replacement of Amide and Peptide Bonds
Takeo Taguchi and Hikaru Yanai
Perfluorinated Heteroaromatic Systems as Scaffolds for Drug Discovery
David Armstrong, Matthew W. Cartwright, Emma L. Parks, Graham Pattison, Graham Sandford, Rachel Slater, Ian Wilson John A. Christopher, David D. Miller, Paul W. Smith, and Antonio Vong
gem-Difl uorocyclopropanes as Key Building Blocks for Novel Biologically Active Molecules 313
Toshiyuki Itoh
Fluorous Mixture Synthesis (FMS) of Drug-like Molecules and Enantiomers, Stereoisomers, and Analogues of Natural Products
Wei Zhang
Fluorine-18 Radiopharmaceuticals
Michael R. Kilbourn and Xia Shao
Applications of Fluorinated Amino Acids and Peptides to Chemical Biology and Pharmacology
Application of Artificial Model Systems to Study the Interactions of Fluorinated Amino Acids within the Native Environment of Coiled Coil Proteins

Mario Salwiczek, Toni Vagt, and Beate Koksch
Fluorinated Amino Acids and Biomolecules in Protein Design and Chemical Biology
He Meng, Ginevra A. Clark, and Krishna Kumar
Effects of Fluorination on the Bioorganic Properties of Methionine
John F. Honek
Structure Analysis of Membrane-Active Peptides Using 19F-labeled Amino Acids and Solid-State NMR
Parvesh Wadhwani and Erik Strandberg
Study of Metabolism of Fluorine-containing Drugs Using In Vivo Magnetic Resonance Spectroscopy
Erika Schneider and Roger Lin
Appendix
Approved Active Pharmaceutical Ingredients Containing Fluorine

Elizabeth Pollina Cormier, Manisha Das, and Iwao Ojima
Section 1: Fluorine-containing Drugs for Human Use Approved by FDA in the United States
Section 2: Fluorine-containing Drugs for Veterinary Use Approved by FDA in the United States
Index
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