Bioactive Carboxylic Compound Classes: Pharmaceuticals and Agrochemicals

Following the successful and proven concept used in Bioactive Heterocyclic Compound Classes by the same editors, this book is the first to present approved pharmaceutical and agrochemical compounds classified by their carboxylic acid functionality in one handy volume. Each of the around 40 chapters describes one or two typical syntheses of a specific compound class and provides concise information on the history of development, mode of action, biological activity and field of application, as well as structure–activity relationships. In addition, similarities and differences between pharmaceuticals and agrochemicals are discussed in the introduction. Written by a team of experts in the field, this is a useful reference for researchers in academia and chemical or pharmaceutical companies working in the field of total synthesis and natural product chemistry, drug development, and crop protection research. INDICE: List of Contributors XV .Preface XXI .1 Different Roles of Carboxylic Functions in Pharmaceuticals and Agrochemicals 1Clemens Lamberth and Jürgen Dinges .1.1 Introduction 1 .1.2 Solubilizer 1 .1.3 Pharmacophore 3 .1.4 Prodrug 4 .1.5 Bioisosteric Replacement 6 .1.6 Scaffold 8 .1.7 Conclusion 9 .Part I Neurology 13 .2 Carboxylic Ester Containing Norepinephrine Dopamine Reuptake Inhibitors (NDRIs) 15David J. O?Neill .2.1 Introduction 15 .2.2 History 15 .2.3 Synthesis 17 .2.4 Mode of Action 21 .2.5 Structure Activity Relationships 22 .3 Analgesic and Anesthetic Amides 27Thomas Erhard .3.1 Introduction 27 .3.2 History 27 .3.3 Synthesis 30 .3.4 Mode of Action 33 .3.5 Structure Activity Relationships 34 .Part II Cardiovascular Diseases 39 .4 Fibrate Acids and Esters for the Treatment of Hyperlipidemia (PPAR Activators) 41Gavin O?Mahony .4.1 Introduction 41 .4.2 History 42 .4.3 Synthesis 45 .4.4 Mode of Action 48 .4.5 Structure Activity Relationships 50 .5 Antiplatelet 2–Hydroxy Thienopyridine Ester Derivatives for the Reduction of Thrombotic Cardiovascular Events 57Modesto de Candia, Nunzio Denora, and Cosimo D. Altomare .5.1 Introduction 57 .5.2 History 57 .5.3 Synthesis 60 .5.4 Mode of Action 62 .5.5 Structure Activity Relationships 67 .6 Carboxylic Acids and Lactones as HMG–CoA Reductase Inhibitors 71Xiang–Yang Ye and Pratik Devasthale .6.1 Introduction 71 .6.2 History 72 .6.3 Synthesis 73 .6.4 Mode of Action 80 .6.5 Structure Activity Relationship 81 .7 Angiotensin II Receptor Antagonists with Carboxylic Functionalities in Cardiovascular Disease 87Steve Swann and Simone Bigi .7.1 Introduction 87 .7.2 History 89 .7.3 Synthesis 90 .7.4 Mode of Action 95 .7.5 Structure Activity Relationships 96 .8 Carboxylic Acid Containing Direct Thrombin Inhibitors for the Treatment of Thromboembolic Diseases 103Harry R. Chobanian and Mathew M. Yanik .8.1 Introduction 103 .8.2 History 104 .8.3 Synthesis 106 .8.4 Mode of Action 108 .8.5 Structure Activity Relationship 109 .Part III Infectious Diseases 115 .9 Tetracycline Amide Antibiotics 117Ingo Janser .9.1 Introduction 117 .9.2 History 120 .9.2.1 First–Generation Tetracyclines The Discovery 120 .9.2.2 Second–Generation Semisynthetic Tetracyclines 121 .9.2.3 Tetracycline Resistance 122 .9.2.4 Third–Generation Tetracyclines 123 .9.3 Synthesis 123 .9.4 Mode of Action 127 .9.5 Structure Activity Relationships 128 .10 Carboxylic–Acid–Based Neuraminidase Inhibitors 133Stacy Van Epps .10.1 Introduction 133 .10.2 History 133 .10.3 Synthesis 136 .10.4 Mode of Action 142 .10.5 Structure Activity Relationships 143 .11 Oxazolidinone Amide Antibiotics 149Cristiana A. Zaharia, Saverio Cellamare, and Cosimo D. Altomare .11.1 Introduction 149 .11.2 History 150 .11.3 Synthesis 153 .11.4 Mechanism of Action 156 .11.5 Structure Activity Relationships 162 .12 Sovaldi, an NS5B RNA Polymerase–Inhibiting Carboxylic Acid Ester Used for the Treatment of Hepatitis C Infection 167Alastair Donald .12.1 Introduction 167 .12.2 History 168 .12.3 Synthesis 170 .12.4 Mode of Action 172 .12.5 Structure Activity Relationships 173 .Part IV Metabolic Diseases 177 .13 Dipeptidyl Peptidase–4 (DPP–4)–Inhibiting Amides for the Treatment of Diabetes 179Naomi S. Rajapaksa and Xiaodong Lin .13.1 Introduction 179 .13.2 History 179 .13.3 Synthesis 184 .13.4 Mode of Action 187 .13.5 Structure Activity Relationships 188 .Part V Oncology 197 .14 Ibrutinib, a Carboxylic Acid Amide Inhibitor of Bruton?s Tyrosine Kinase 199Timothy D. Owens .14.1 Introduction 199 .14.2 History 199 .14.3 Synthesis 201 .14.4 Mechanism of Action 202 .14.5 Structure Activity Relationships 203 .Part VI Anti–Inflammatory Drugs 209 .15 Fumaric Acid Esters 211Tony S. Gibson .15.1 Introduction 211 .15.2 History 211 .15.3 Synthesis 213 .15.4 Mode of Action 213 .15.5 Structure Activity Relationships 215 .16 Carboxylic Acid Nonsteroidal Anti–Inflammatory Drugs (NSAIDs) 221Yan Lou and Jiang Zhu .16.1 Introduction 221 .16.2 History 222 .16.3 Synthesis 224 .16.4 Mode of Action 228 .16.5 Structure Activity Relationships 230 .17 Carboxylic–Acid–Containing Antihistamines 237Irini Akritopoulou–Zanze .17.1 Introduction 237 .17.2 History 237 .17.3 Synthesis 239 .17.4 Mode of Action 241 .17.5 Structure Activity Relationship 241 .18 Corticosteroid Carboxylic Acid Esters 245Maurizio Franzini .18.1 Introduction 245 .18.2 History 249 .18.3 Synthesis 252 .18.4 Mode of Action 258 .18.5 Structure Activity Relationships 261 .Part VII Ophthalmology 269 .19 Prostaglandins with Carboxylic Functionalities for the Treatment of Glaucoma 271Fabrizio Carta and Claudiu T. Supuran .19.1 Introduction 271 .19.2 History 271 .19.3 Synthesis 272 .19.4 Mode of Action 276 .19.5 Structure Activity Relationship (SAR) 278 .Part VIII Weed Control 281 .20 Herbicidal Carboxylic Acids as Synthetic Auxins 283Paul Schmitzer, Jeffrey Epp, Roger Gast,William Lo, and Jeff Nelson .20.1 Introduction 283 .20.2 History 283 .20.3 Synthesis 286 .20.4 Mode of Action 289 .20.5 Biological Activity 289 .21 Chloroacetamide Herbicides 293Clemens Lamberth .21.1 Introduction 293 .21.2 History 293 .21.3 Synthesis 296 .21.4 Mode of Action 297 .21.5 Biological Activity 299 .21.6 Structure Activity Relationship 300 .22 Carboxylic–Acid–Containing Sulfonylurea Herbicides 303Atul Puri and Paul H. Liang .22.1 Introduction 303 .22.2 History 303 .22.3 Synthesis 305 .22.4 Mode of Action 306 .22.5 Biological Activity 308 .22.6 Structure Activity Relationship 309 .23 Amino Acids as Nonselective Herbicides 315Stephane Jeanmart .23.1 Introduction 315 .23.2 History 316 .23.3 Synthesis 317 .23.4 Mode of Action 319 .23.5 Biological Activity 320 .23.6 Structure Activity Relationships 321 .24 Herbicidal Aryloxyphenoxypropionate Inhibitors of Acetyl–CoA Carboxylase 325William G.Whittingham .24.1 Introduction 325 .24.2 History 325 .24.3 Synthesis 327 .24.4 Mode of Action 329 .24.5 Biological Activity 330 .24.6 Structure Activity Relationships 331 .25 Pyridines Substituted by an Imidazolinone and a Carboxylic Acid as Acetohydroxyacid–Synthase–Inhibiting Herbicides 339Dale Shaner .25.1 Introduction 339 .25.2 History 339 .25.3 Synthesis 341 .25.4 Mode of Action 342 .25.5 Biological Activity 342 .25.6 Structure Activity Relationship 344 .26 Carboxylic–Acid–Containing Protoporphyrinogen–IX–Oxidase–Inhibiting Herbicides 347George Theodoridis .26.1 Introduction 347 .26.2 History 347 .26.3 Synthesis 350 .26.4 Mode of Action 351 .26.5 Biological Activity 352 .26.6 Structure Activity Relationship 352 .Part IX Disease Control 357 .27 Phenylamide Fungicides 359Laura Quaranta .27.1 Introduction 359 .27.2 History 359 .27.3 Synthesis 362 .27.4 Mode of Action 364 .27.5 Biological Activity 365 .27.6 Structure Activity Relationship 365 .28 Complex III Inhibiting Strobilurin Esters, Amides, and Carbamates as Broad–Spectrum Fungicides 371Clemens Lamberth .28.1 Introduction 371 .28.2 History 371 .28.3 Synthesis 375 .28.4 Mode of Action 379 .28.5 Biological Activity 380 .28.6 Structure Activity Relationship 381 .29 Scytalone–Dehydratase–Inhibiting Carboxamides for the Control of Rice Blast 385Andrew E. Taggi .29.1 Introduction 385 .29.2 History 385 .29.3 Synthesis 389 .29.4 Mode of Action 390 .29.5 Biological Activity 391 .29.6 Structure Activity Relationships 392 .30 Carboxylic Acid Amide Fungicides for the Control of Downy Mildew Diseases 395Clemens Lamberth .30.1 Introduction 395 .30.2 History 395 .30.3 Synthesis 397 .30.4 Mode of Action 399 .30.5 Biological Activity 400 .30.6 Structure Activity Relationship 400 .31 Fungicidal Succinate–Dehydrogenase–Inhibiting Carboxamides 405Harald Walter .31.1 Introduction 405 .31.2 History 406 .31.3 Synthesis 409 .31.4 Mode of Action and Importance of Respiration Inhibitors 415 .31.5 Biological Activity and Market Impact 416 .31.6 Structure Activity Relationships 418 .Part X Insect Control 427 .32 Esters and Carbamates as Insecticidal Juvenile Hormone Mimics 429Sebastian Rendler .32.1 Introduction 429 .32.2 History 429 .32.3 Synthesis 431 .32.4 Mode of Action 433 .32.5 Biological Activity 434 .32.6 Structure Activity Relationship 434 .33 N–Benzoyl–N –Phenyl Ureas as Insecticides, Acaricides, and Termiticides 439Peter Jeschke .33.1 Introduction 439 .33.2 History 439 .33.3 Synthesis 442 .33.4 Mode of Action 445 .33.5 Biological Activity 446 .33.6 Structure Activity Relationship 448 .34 Pyrethroid Esters for the Control of Insect Pests 453Régis Mondière and Fides Benfatti .34.1 Introduction 453 .34.2 History 454 .34.3 Synthesis 457 .34.4 Mode of Action 459 .34.5 Biological Activity 461 .34.6 Structure Activity Relationship 462 .35 Ecdysone Receptor Agonistic Dibenzoyl Hydrazine Insecticides 467Ottmar F. Hüter .35.1 Introduction 467 .35.2 History 467 .35.3 Synthesis 468 .35.4 Mode of Action 471 .35.5 Biological Activity 473 .35.6 Structure Activity Relationship 473 .36 Diamide Insecticides as Ryanodine Receptor Activators 479André Jeanguenat .36.1 Introduction 479 .36.2 History 479 .36.3 Synthesis 481 .36.4 Mode of Action 485 .36.5 Biological Activity 485 .36.6 Structure Activity Relationship 486 .Index 491

• ISBN: 978-3-527-33947-1
• Editorial: Wiley VCH
• Encuadernacion: Cartoné
• Páginas: 525
• Fecha Publicación: 13/07/2016
• Nº Volúmenes: 1
• Idioma: Inglés