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Bioactive Carboxylic Compound Classes: Pharmaceuticals and Agrochemicals

Bioactive Carboxylic Compound Classes: Pharmaceuticals and Agrochemicals

Clemens Lamberth (Editor), Jürgen Dinges (Editor)

ISBN: 978-3-527-69394-8

Jun 2016

525 pages

$172.99

Description

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.

List of Contributors XV

Preface XXI

1 Different Roles of Carboxylic Functions in Pharmaceuticals and Agrochemicals 1
Clemens 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) 15
David 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 27
Thomas 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 (PPARα Activators) 41
Gavin 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 57
Modesto 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 71
Xiang-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 87
Steve 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 103
Harry 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 117
Ingo 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 133
Stacy 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 149
Cristiana 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 167
Alastair 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 179
Naomi 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 199
Timothy 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 211
Tony 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) 221
Yan 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 237
Irini 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 245
Maurizio 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 271
Fabrizio 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 283
Paul 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 293
Clemens 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 303
Atul 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 315
Stephane 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 325
William 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 339
Dale 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 347
George 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 359
Laura 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 371
Clemens 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 385
Andrew 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 395
Clemens 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 405
Harald 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 429
Sebastian 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 439
Peter 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 453
Régis 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 467
Ottmar 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 479
André 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