Bioorganic and medicinal chemistry of fluorine:
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| Main Authors: | , |
|---|---|
| Format: | Book |
| Language: | English French |
| Published: |
Hoboken, N.J.
Wiley
2008
Chichester John Wiley |
| Subjects: | |
| Online Access: | Inhaltsverzeichnis |
| Item Description: | Includes bibliographical references and index |
| Physical Description: | XVII, 365 S. Ill. |
| ISBN: | 9780470278307 |
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MARC
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| 020 | |a 9780470278307 |c (hbk.) : £52.95 hbk. : £52.95 : CIP entry (May) |9 978-0-470-27830-7 | ||
| 035 | |a (OCoLC)180081218 | ||
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| 100 | 1 | |a Bégué, Jean-Pierre |e Verfasser |4 aut | |
| 240 | 1 | 0 | |a Chimie bioorganisme et médicinale du fluor |
| 245 | 1 | 0 | |a Bioorganic and medicinal chemistry of fluorine |c Jean-Pierre Bégué, Danièle Bonnet-Delpon ; transl. from French by Julien Legros |
| 264 | 1 | |a Hoboken, N.J. |b Wiley |c 2008 | |
| 264 | 1 | |a Chichester |b John Wiley | |
| 300 | |a XVII, 365 S. |b Ill. | ||
| 336 | |b txt |2 rdacontent | ||
| 337 | |b n |2 rdamedia | ||
| 338 | |b nc |2 rdacarrier | ||
| 500 | |a Includes bibliographical references and index | ||
| 650 | 4 | |a Fluorine compounds / Therapeutic use | |
| 650 | 4 | |a Fluorine / Physiological effect | |
| 650 | 4 | |a Organofluorine compounds | |
| 650 | 4 | |a Bioorganic chemistry | |
| 650 | 0 | 7 | |a Physiologie |0 (DE-588)4045981-0 |2 gnd |9 rswk-swf |
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Record in the Search Index
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|---|---|
| adam_text | CONTENTS
Foreword xiii
Preface to the English Edition xvii
1 General Remarks on Structural, Physical, and Chemical
Properties of Fluorinated Compounds 1
1.1 Structural Effects / 2
1.2 Physical Properties / 3
1.2.1 Boiling Point / 3
1.2.2 Surface Tension and Activity / 5
1.2.3 Polarity-Solubility / 6
1.2.4 Lipophilicity / 7
1.3 Effects on Electronic Properties and Reactivity / 9
1.3.1 Effects of Fluorination on Bond Energies and Reactivity / 9
1.3.2 Effects of Fluorination on the Electronic
Repartition of a Molecule / 10
1.3.3 Acidity, Basicity, and Hydrogen Bond / 12
1.3.4 Steric Effects / 15
1.3.5 Fluorination Effects on the Stability of Reaction
Intermediates (Carbocations, Carbanions, and Radicals) / 16
References / 21
2 Overview on the Preparation of Fluorinated Compounds 23
2.1 Preparation of Monofluorinated Compounds / 24
2.1.1 Nucleophilic Fluorination / 24
2.1.2 Electrophilic Fluorination / 26
2.1.3 Formation of Carbon-Carbon Bonds Starting
from Monofluorinated Synthons / 27
v
Vi CONTENTS
2.2 Preparation of Difluorinated Compounds / 31
2.2.1 Nucleophilic Fluorination / 31
2.2.2 Electrophilic Fluorination / 31
2.2.3 Starting from Di- and Trifluoromethyl Compounds / 31
2.3 Preparation of Trifluoromethyl Compounds / 42
2.3.1 Fluorination / 42
2.3.2 Nucleophilic Trifiuoromethylation / 42
2.3.3 Electrophilic Trifiuoromethylation / 48
2.3.4 Radical Trifiuoromethylation / 49
2.3.5 Metal-Catalyzed Trifiuoromethylation / 49
2.3.6 Formation of Carbon-Carbon Bonds
from Trifluoromethyl Compounds / 50
2.4 Synthesis of Perfluoroalkyl Compounds / 61
References / 62
3 Effects of Fluorine Substitution on Biological Properties 72
3.1 Affinity for the Macromolecule Target / 73
3.1.1 Steric Effects / 73
3.1.2 Conformational Changes / 74
3.1.3 Dipolar Interactions and Electric Field / 75
3.1.4 Hydrogen Bonds and Other Weak Interactions / 75
3.1.5 pKa of Amines / 79
3.1.6 Fluorous Interactions / 80
3.2 Absorption / 80
3.2.1 Lipophilicity / 80
3.2.2 pATa and Solubility / 82
3.3 Metabolism / 84
3.3.1 Oxidative Metabolism / 84
3.3.2 Hydrolytic Metabolism / 87
3.4 Modification of Chemical Reactivity: Enzyme Inhibitors / 89
3.4.1 Analogue of Substrates as Inhibitors / 90
3.4.2 Inhibition by Stabilization or Destabilization
of Intermediates of Biological Processes / 91
3.4.3 Irreversible Inhibition with Mechanism-Based
Inhibitors (Suicide Substrates) / 93
References / 95
CONTENTS Vii
4 Fluorinated Analogues of Natural Products 99
4.1 Fluorinated Products in Nature / 99
4.2 Steroids / 101
4.2.1 Corticosteroids / 101
4.2.2 Steroids with Trifluoromethyl Groups
in Angular Position / 103
4.2.3 Fluorinated Analogues of Metabolites of Vitamin D3 / 105
4.2.4 Other Fluorinated Steroids / 108
4.3 Terpenes / 108
4.3.1 Artemisinin / 108
4.3.2 Taxol / 110
4.4 Pigments and Vitamins /111
4.4.1 Retinoids /111
4.4.2 Carotenoids / 115
4.4.3 Vitamin D / 116
4.4.4 Vitamins E and K / 116
4.4.5 Porphyrins / 117
4.5 Lipids and Prostanoids / 119
4.6 Pheromones and Toxins / 125
4.7 Alkaloids / 129
4.7.1 Vinca Alkaloids / 129
4.7.2 Cinchona Alkaloids / 131
4.7.3 Camptothecin / 132
4.7.4 Other Fluorinated Alkaloids / 133
4.8 Macrolides / 133
4.8.1 Epothilone / 133
4.8.2 Erythromycin / 134
4.8.3 Amphotericin B / 135
4.8.4 Avermectin / 136
4.9 Anthracyclines / 138
References / 139
5 Fluorinated Derivatives of u-Amino Acids and Proteins 146
5.1 Fluorinated Aliphatic Amino Acids / 147
5.1.1 Alanines / 147
VJii CONTENTS
5.1.2 Valines, Leucines, and Isoleucines / 151
5.1.3 Prolines / 154
5.2 Aromatic Amino Acids: Phenylalanine, Tyrosine,
Histidine, and Tryptophan / 156
5.3 Functional Fluorinated Amino Acids / 158
5.3.1 Serines and Threonines / 158
5.3.2 Aspartic Acids and Arginines / 159
5.3.3 Glutamic Acids and Glutamines / 161
5.3.4 Lysine, Ornithine, and Arginine / 161
5.3.5 Cysteines and Methionines / 163
5.4 a-Fluoroalkyl Amino Acids / 164
5.4.1 Mono- and Difluoromethyl Amino Acids / 165
5.4.2 a-Trifluoromethyl Amino Acids / 165
5.5 Incorporation of Fluorinated Amino Acids
into Peptides and Proteins / 169
5.5.1 Polypeptides / 169
5.5.2 Proteins / 171
References / 173
6 Saccharidic Fluorinated Derivatives 180
6.1 Glycosyl Fluorides / 181
6.2 Mono- and Diftuorinated Analogues of Sugars / 181
6.2.1 Fluorinated Furanoses and Nucleosides / 181
6.2.2 Fluorinated Pyranoses / 190
6.3 Fluoromethyl Derivatives of Sugars / 197
6.3.1 Difluorovinyl Compounds / 197
6.3.2 Difluoromethylene-C-Glycosides / 197
6.3.3 C-Difiuoromethyl Glycosides / 200
6.3.4 Trifluoromethylated Sugars / 202
6.4 Perfluoroalkylated Sugars / 209
6.4.1 Preparation of C-Perfluoroalkyl Sugars / 210
6.4.2 O- and S-Fluoroalkyl Glycosides / 211
6.4.3 Applications of Amphiphilic
Fluoroalkyl Sugars / 214
References / 216
CONTENTS ix
7 Inhibition of Enzymes by Fluorinated Compounds 223
7.1 Substrate Analogues / 225
7.1.1 Fluorine Replaces a Hydrogen Involved
in the Catalytic Cycle / 225
7.1.2 Fluorine Replaces a Hydroxyl / 227
7.1.3 Fluorinated Analogues of Substrates in Which
Fluorine is Not Directly Involved in the Inhibition / 230
7.2 Destabilization of Reaction Intermediates (or of Transition States)
of Enzymatic Processes by Fluorinated Groups / 242
7.2.1 Prenyl Transfer / 242
7.2.2 Inhibition of Glycosidases and Glycosyltransferases / 242
7.2.3 Inhibition of UDP-GlcNAC
Enolpyruvyltransferase (MurZ) / 244
7.2.4 Enolpyruvate Shikimate Phosphate Synthase (EPSPS) / 245
7.3 Inhibitors that are Analogues of the Transition
State: Di- and Trifluoromethyl Ketones / 246
7.3.1 Serine Enzymes / 246
7.3.2 Inhibition of Aspartyl Enzymes / 250
7.3.3 Inhibition of Metalloproteases / 254
7.3.4 Cysteine Protease and Thiol Enzymes / 254
7.4 Mechanism-Based Inhibitors / 256
7.4.1 Inhibition of Pyridoxal Phosphate Enzymes / 257
7.4.2 Thymidylate Synthase / 261
7.4.3 Inhibition of Monoamine Oxidases / 262
7.4.4 D-Ala-D-Ala Dipeptidase (VanX) / 264
7.4.5 Inhibition of Ribonucleotide Diphosphate Reductase / 264
7.4.6 Inhibition of 5-Adenosylhomocysteine Hydrolase / 265
7.4.7 Inhibition of Cytidine-5 -diphosphate-D-Glucose
4,6-Dehydratase (CDP D-Glucose 4,6-Dehydratase) / 266
7.4.8 Other Irreversible Inhibitors / 267
7.5 Fluorinated Inhibitors Involving a Still Unknown Mechanism / 268
7.5.1 Inhibition of the Steroid C17(20)lyase / 268
7.5.2 Phosphatidylinositol Phospholipase C (PI-PLC) / 268
7.5.3 Inhibition of the Protein of Transfer of Cholesteryl Esters / 269
7.5.4 /3-Fluoropolyamines as Inhibitors of the
Biosynthesis of Polyamines / 270
7.5.5 Inhibition of the Biosynthesis of Cholesterol / 272
References / 272
X CONTENTS
8 Fluorinated Drugs 279
8.1 Antitumor and Antiviral Fluorinated Drugs / 280
8.1.1 Fluoronucleosides / 280
8.1.2 Other Antitumor and Antiviral Drugs / 284
8.2 Anti-infectious Drugs / 289
8.2.1 Fluorinated Antibiotic Drugs / 289
8.2.2 Antifungal Drugs / 297
8.2.3 Fluorinated Drugs for Parasitic Diseases / 299
8.3 Drugs for CNS Disorders / 300
8.3.1 Neuroleptics / 300
8.3.2 Drugs for Depressive Disorders / 302
8.3.3 Anxiolytics and Sedatives / 304
8.3.4 Other Drugs for CNS Disorders / 304
8.4 Drugs of Inflammatory and Immunity Disorders / 308
8.4.1 Fluorocorticosteroids / 308
8.4.2 H, Antagonist Antiallergics / 314
8.4.3 Drugs for Asthma and Respiratory Disorders / 314
8.4.4 Analgesic and Antiarthritic Drugs / 316
8.5 Drugs for Cardiovascular Disorders / 320
8.5.1 Cholesterol Lowering Drugs / 320
8.5.2 Drugs for Hypertension / 321
8.5.3 Drugs for Arrhythmias / 324
8.5.4 Antithrombosis and Anticoagulant Fluorinated Agents / 324
8.6 Drugs for Gastrointestinal Disorders / 325
8.6.1 Prevention and Treatment of Ulcer / 325
8.6.2 Antiemetic Agents / 326
8.6.3 Drugs for Bowel Disorders / 327
8.7 Drugs for Endocrine and Metabolic Disorders / 327
8.7.1 Drugs Acting on Steroid Hormone Receptors / 327
8.7.2 Drugs for Benign Prostatic Hypertrophy (BPH) / 329
8.7.3 Drugs for Other Urologic Disorders / 330
8.7.4 Drugs for Calcemia Disorders / 331
8.7.5 Drugs for Diabetes / 331
8.7.6 Drugs for Hepatic Disorders / 333
8.8 Miscellaneous / 334
8.8.1 Drugs for Ophthalmic Disorders / 334
CONTENTS Xi
8.8.2 Drugs for Genetic Disease / 334
8.8.3 Contrast and Diagnostic Agents / 334
8.9 Highly Fluorinated Compounds with Clinical Uses / 335
8.9.1 General Anesthetics / 335
8.9.2 Therapeutic Uses of Perfluorocarbons / 338
8.10 Fluorinated Functions and Motifs in Medicinal Chemistry / 339
8.10.1 Fluorinated Ethers / 339
8.10.2 Fluorinated Alcohols and Amines / 340
8.10.3 Fluorinated Ketones / 340
8.10.4 Fluoroalkyl Groups / 341
Appendix: INN and Trademark Names / 342
References / 347
Index 353
|
| adam_txt |
CONTENTS
Foreword xiii
Preface to the English Edition xvii
1 General Remarks on Structural, Physical, and Chemical
Properties of Fluorinated Compounds 1
1.1 Structural Effects / 2
1.2 Physical Properties / 3
1.2.1 Boiling Point / 3
1.2.2 Surface Tension and Activity / 5
1.2.3 Polarity-Solubility / 6
1.2.4 Lipophilicity / 7
1.3 Effects on Electronic Properties and Reactivity / 9
1.3.1 Effects of Fluorination on Bond Energies and Reactivity / 9
1.3.2 Effects of Fluorination on the Electronic
Repartition of a Molecule / 10
1.3.3 Acidity, Basicity, and Hydrogen Bond / 12
1.3.4 Steric Effects / 15
1.3.5 Fluorination Effects on the Stability of Reaction
Intermediates (Carbocations, Carbanions, and Radicals) / 16
References / 21
2 Overview on the Preparation of Fluorinated Compounds 23
2.1 Preparation of Monofluorinated Compounds / 24
2.1.1 Nucleophilic Fluorination / 24
2.1.2 Electrophilic Fluorination / 26
2.1.3 Formation of Carbon-Carbon Bonds Starting
from Monofluorinated Synthons / 27
v
Vi CONTENTS
2.2 Preparation of Difluorinated Compounds / 31
2.2.1 Nucleophilic Fluorination / 31
2.2.2 Electrophilic Fluorination / 31
2.2.3 Starting from Di- and Trifluoromethyl Compounds / 31
2.3 Preparation of Trifluoromethyl Compounds / 42
2.3.1 Fluorination / 42
2.3.2 Nucleophilic Trifiuoromethylation / 42
2.3.3 Electrophilic Trifiuoromethylation / 48
2.3.4 Radical Trifiuoromethylation / 49
2.3.5 Metal-Catalyzed Trifiuoromethylation / 49
2.3.6 Formation of Carbon-Carbon Bonds
from Trifluoromethyl Compounds / 50
2.4 Synthesis of Perfluoroalkyl Compounds / 61
References / 62
3 Effects of Fluorine Substitution on Biological Properties 72
3.1 Affinity for the Macromolecule Target / 73
3.1.1 Steric Effects / 73
3.1.2 Conformational Changes / 74
3.1.3 Dipolar Interactions and Electric Field / 75
3.1.4 Hydrogen Bonds and Other Weak Interactions / 75
3.1.5 pKa of Amines / 79
3.1.6 Fluorous Interactions / 80
3.2 Absorption / 80
3.2.1 Lipophilicity / 80
3.2.2 pATa and Solubility / 82
3.3 Metabolism / 84
3.3.1 Oxidative Metabolism / 84
3.3.2 Hydrolytic Metabolism / 87
3.4 Modification of Chemical Reactivity: Enzyme Inhibitors / 89
3.4.1 Analogue of Substrates as Inhibitors / 90
3.4.2 Inhibition by Stabilization or Destabilization
of Intermediates of Biological Processes / 91
3.4.3 Irreversible Inhibition with Mechanism-Based
Inhibitors (Suicide Substrates) / 93
References / 95
CONTENTS Vii
4 Fluorinated Analogues of Natural Products 99
4.1 Fluorinated Products in Nature / 99
4.2 Steroids / 101
4.2.1 Corticosteroids / 101
4.2.2 Steroids with Trifluoromethyl Groups
in Angular Position / 103
4.2.3 Fluorinated Analogues of Metabolites of Vitamin D3 / 105
4.2.4 Other Fluorinated Steroids / 108
4.3 Terpenes / 108
4.3.1 Artemisinin / 108
4.3.2 Taxol / 110
4.4 Pigments and Vitamins /111
4.4.1 Retinoids /111
4.4.2 Carotenoids / 115
4.4.3 Vitamin D / 116
4.4.4 Vitamins E and K / 116
4.4.5 Porphyrins / 117
4.5 Lipids and Prostanoids / 119
4.6 Pheromones and Toxins / 125
4.7 Alkaloids / 129
4.7.1 Vinca Alkaloids / 129
4.7.2 Cinchona Alkaloids / 131
4.7.3 Camptothecin / 132
4.7.4 Other Fluorinated Alkaloids / 133
4.8 Macrolides / 133
4.8.1 Epothilone / 133
4.8.2 Erythromycin / 134
4.8.3 Amphotericin B / 135
4.8.4 Avermectin / 136
4.9 Anthracyclines / 138
References / 139
5 Fluorinated Derivatives of u-Amino Acids and Proteins 146
5.1 Fluorinated Aliphatic Amino Acids / 147
5.1.1 Alanines / 147
VJii CONTENTS
5.1.2 Valines, Leucines, and Isoleucines / 151
5.1.3 Prolines / 154
5.2 Aromatic Amino Acids: Phenylalanine, Tyrosine,
Histidine, and Tryptophan / 156
5.3 Functional Fluorinated Amino Acids / 158
5.3.1 Serines and Threonines / 158
5.3.2 Aspartic Acids and Arginines / 159
5.3.3 Glutamic Acids and Glutamines / 161
5.3.4 Lysine, Ornithine, and Arginine / 161
5.3.5 Cysteines and Methionines / 163
5.4 a-Fluoroalkyl Amino Acids / 164
5.4.1 Mono- and Difluoromethyl Amino Acids / 165
5.4.2 a-Trifluoromethyl Amino Acids / 165
5.5 Incorporation of Fluorinated Amino Acids
into Peptides and Proteins / 169
5.5.1 Polypeptides / 169
5.5.2 Proteins / 171
References / 173
6 Saccharidic Fluorinated Derivatives 180
6.1 Glycosyl Fluorides / 181
6.2 Mono- and Diftuorinated Analogues of Sugars / 181
6.2.1 Fluorinated Furanoses and Nucleosides / 181
6.2.2 Fluorinated Pyranoses / 190
6.3 Fluoromethyl Derivatives of Sugars / 197
6.3.1 Difluorovinyl Compounds / 197
6.3.2 Difluoromethylene-C-Glycosides / 197
6.3.3 C-Difiuoromethyl Glycosides / 200
6.3.4 Trifluoromethylated Sugars / 202
6.4 Perfluoroalkylated Sugars / 209
6.4.1 Preparation of C-Perfluoroalkyl Sugars / 210
6.4.2 O- and S-Fluoroalkyl Glycosides / 211
6.4.3 Applications of Amphiphilic
Fluoroalkyl Sugars / 214
References / 216
CONTENTS ix
7 Inhibition of Enzymes by Fluorinated Compounds 223
7.1 Substrate Analogues / 225
7.1.1 Fluorine Replaces a Hydrogen Involved
in the Catalytic Cycle / 225
7.1.2 Fluorine Replaces a Hydroxyl / 227
7.1.3 Fluorinated Analogues of Substrates in Which
Fluorine is Not Directly Involved in the Inhibition / 230
7.2 Destabilization of Reaction Intermediates (or of Transition States)
of Enzymatic Processes by Fluorinated Groups / 242
7.2.1 Prenyl Transfer / 242
7.2.2 Inhibition of Glycosidases and Glycosyltransferases / 242
7.2.3 Inhibition of UDP-GlcNAC
Enolpyruvyltransferase (MurZ) / 244
7.2.4 Enolpyruvate Shikimate Phosphate Synthase (EPSPS) / 245
7.3 Inhibitors that are Analogues of the Transition
State: Di- and Trifluoromethyl Ketones / 246
7.3.1 Serine Enzymes / 246
7.3.2 Inhibition of Aspartyl Enzymes / 250
7.3.3 Inhibition of Metalloproteases / 254
7.3.4 Cysteine Protease and Thiol Enzymes / 254
7.4 Mechanism-Based Inhibitors / 256
7.4.1 Inhibition of Pyridoxal Phosphate Enzymes / 257
7.4.2 Thymidylate Synthase / 261
7.4.3 Inhibition of Monoamine Oxidases / 262
7.4.4 D-Ala-D-Ala Dipeptidase (VanX) / 264
7.4.5 Inhibition of Ribonucleotide Diphosphate Reductase / 264
7.4.6 Inhibition of 5-Adenosylhomocysteine Hydrolase / 265
7.4.7 Inhibition of Cytidine-5'-diphosphate-D-Glucose
4,6-Dehydratase (CDP D-Glucose 4,6-Dehydratase) / 266
7.4.8 Other Irreversible Inhibitors / 267
7.5 Fluorinated Inhibitors Involving a Still Unknown Mechanism / 268
7.5.1 Inhibition of the Steroid C17(20)lyase / 268
7.5.2 Phosphatidylinositol Phospholipase C (PI-PLC) / 268
7.5.3 Inhibition of the Protein of Transfer of Cholesteryl Esters / 269
7.5.4 /3-Fluoropolyamines as Inhibitors of the
Biosynthesis of Polyamines / 270
7.5.5 Inhibition of the Biosynthesis of Cholesterol / 272
References / 272
X CONTENTS
8 Fluorinated Drugs 279
8.1 Antitumor and Antiviral Fluorinated Drugs / 280
8.1.1 Fluoronucleosides / 280
8.1.2 Other Antitumor and Antiviral Drugs / 284
8.2 Anti-infectious Drugs / 289
8.2.1 Fluorinated Antibiotic Drugs / 289
8.2.2 Antifungal Drugs / 297
8.2.3 Fluorinated Drugs for Parasitic Diseases / 299
8.3 Drugs for CNS Disorders / 300
8.3.1 Neuroleptics / 300
8.3.2 Drugs for Depressive Disorders / 302
8.3.3 Anxiolytics and Sedatives / 304
8.3.4 Other Drugs for CNS Disorders / 304
8.4 Drugs of Inflammatory and Immunity Disorders / 308
8.4.1 Fluorocorticosteroids / 308
8.4.2 H, Antagonist Antiallergics / 314
8.4.3 Drugs for Asthma and Respiratory Disorders / 314
8.4.4 Analgesic and Antiarthritic Drugs / 316
8.5 Drugs for Cardiovascular Disorders / 320
8.5.1 Cholesterol Lowering Drugs / 320
8.5.2 Drugs for Hypertension / 321
8.5.3 Drugs for Arrhythmias / 324
8.5.4 Antithrombosis and Anticoagulant Fluorinated Agents / 324
8.6 Drugs for Gastrointestinal Disorders / 325
8.6.1 Prevention and Treatment of Ulcer / 325
8.6.2 Antiemetic Agents / 326
8.6.3 Drugs for Bowel Disorders / 327
8.7 Drugs for Endocrine and Metabolic Disorders / 327
8.7.1 Drugs Acting on Steroid Hormone Receptors / 327
8.7.2 Drugs for Benign Prostatic Hypertrophy (BPH) / 329
8.7.3 Drugs for Other Urologic Disorders / 330
8.7.4 Drugs for Calcemia Disorders / 331
8.7.5 Drugs for Diabetes / 331
8.7.6 Drugs for Hepatic Disorders / 333
8.8 Miscellaneous / 334
8.8.1 Drugs for Ophthalmic Disorders / 334
CONTENTS Xi
8.8.2 Drugs for Genetic Disease / 334
8.8.3 Contrast and Diagnostic Agents / 334
8.9 Highly Fluorinated Compounds with Clinical Uses / 335
8.9.1 General Anesthetics / 335
8.9.2 Therapeutic Uses of Perfluorocarbons / 338
8.10 Fluorinated Functions and Motifs in Medicinal Chemistry / 339
8.10.1 Fluorinated Ethers / 339
8.10.2 Fluorinated Alcohols and Amines / 340
8.10.3 Fluorinated Ketones / 340
8.10.4 Fluoroalkyl Groups / 341
Appendix: INN and Trademark Names / 342
References / 347
Index 353 |
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| author | Bégué, Jean-Pierre Bonnet-Delpon, Danièle |
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| discipline_str_mv | Chemie / Pharmazie |
| format | Book |
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| id | DE-604.BV023361093 |
| illustrated | Illustrated |
| index_date | 2024-07-02T21:09:12Z |
| indexdate | 2024-07-09T21:16:50Z |
| institution | BVB |
| isbn | 9780470278307 |
| language | English French |
| oai_aleph_id | oai:aleph.bib-bvb.de:BVB01-016544551 |
| oclc_num | 180081218 |
| open_access_boolean | |
| owner | DE-19 DE-BY-UBM DE-703 DE-83 |
| owner_facet | DE-19 DE-BY-UBM DE-703 DE-83 |
| physical | XVII, 365 S. Ill. |
| publishDate | 2008 |
| publishDateSearch | 2008 |
| publishDateSort | 2008 |
| publisher | Wiley John Wiley |
| record_format | marc |
| spelling | Bégué, Jean-Pierre Verfasser aut Chimie bioorganisme et médicinale du fluor Bioorganic and medicinal chemistry of fluorine Jean-Pierre Bégué, Danièle Bonnet-Delpon ; transl. from French by Julien Legros Hoboken, N.J. Wiley 2008 Chichester John Wiley XVII, 365 S. Ill. txt rdacontent n rdamedia nc rdacarrier Includes bibliographical references and index Fluorine compounds / Therapeutic use Fluorine / Physiological effect Organofluorine compounds Bioorganic chemistry Physiologie (DE-588)4045981-0 gnd rswk-swf Fluororganische Verbindungen (DE-588)4154846-2 gnd rswk-swf Naturstoffchemie (DE-588)4171332-1 gnd rswk-swf Naturstoffchemie (DE-588)4171332-1 s Fluororganische Verbindungen (DE-588)4154846-2 s DE-604 Physiologie (DE-588)4045981-0 s Bonnet-Delpon, Danièle Verfasser aut HBZ Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=016544551&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Bégué, Jean-Pierre Bonnet-Delpon, Danièle Bioorganic and medicinal chemistry of fluorine Fluorine compounds / Therapeutic use Fluorine / Physiological effect Organofluorine compounds Bioorganic chemistry Physiologie (DE-588)4045981-0 gnd Fluororganische Verbindungen (DE-588)4154846-2 gnd Naturstoffchemie (DE-588)4171332-1 gnd |
| subject_GND | (DE-588)4045981-0 (DE-588)4154846-2 (DE-588)4171332-1 |
| title | Bioorganic and medicinal chemistry of fluorine |
| title_alt | Chimie bioorganisme et médicinale du fluor |
| title_auth | Bioorganic and medicinal chemistry of fluorine |
| title_exact_search | Bioorganic and medicinal chemistry of fluorine |
| title_exact_search_txtP | Bioorganic and medicinal chemistry of fluorine |
| title_full | Bioorganic and medicinal chemistry of fluorine Jean-Pierre Bégué, Danièle Bonnet-Delpon ; transl. from French by Julien Legros |
| title_fullStr | Bioorganic and medicinal chemistry of fluorine Jean-Pierre Bégué, Danièle Bonnet-Delpon ; transl. from French by Julien Legros |
| title_full_unstemmed | Bioorganic and medicinal chemistry of fluorine Jean-Pierre Bégué, Danièle Bonnet-Delpon ; transl. from French by Julien Legros |
| title_short | Bioorganic and medicinal chemistry of fluorine |
| title_sort | bioorganic and medicinal chemistry of fluorine |
| topic | Fluorine compounds / Therapeutic use Fluorine / Physiological effect Organofluorine compounds Bioorganic chemistry Physiologie (DE-588)4045981-0 gnd Fluororganische Verbindungen (DE-588)4154846-2 gnd Naturstoffchemie (DE-588)4171332-1 gnd |
| topic_facet | Fluorine compounds / Therapeutic use Fluorine / Physiological effect Organofluorine compounds Bioorganic chemistry Physiologie Fluororganische Verbindungen Naturstoffchemie |
| url | http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=016544551&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
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