Bioactive carboxylic compound classes: pharmaceuticals and agrochemicals

529 Pages·2016·13.13 MB·English

by  Dinges

Editedby
ClemensLamberthand
JürgenDinges
BioactiveCarboxylicCompoundClasses

EditedbyClemensLamberthandJürgenDinges
Bioactive Carboxylic Compound Classes
PharmaceuticalsandAgrochemicals
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V
Contents
ListofContributors XV
Preface XXI
1 DifferentRolesofCarboxylicFunctionsinPharmaceuticalsand
Agrochemicals 1
ClemensLamberthandJürgenDinges
1.1 Introduction 1
1.2 Solubilizer 1
1.3 Pharmacophore 3
1.4 Prodrug 4
1.5 BioisostericReplacement 6
1.6 Scaffold 8
1.7 Conclusion 9
References 9
PartI Neurology 13
2 CarboxylicEsterContainingNorepinephrine–DopamineReuptake
Inhibitors(NDRIs) 15
DavidJ.O’Neill
2.1 Introduction 15
2.2 History 15
2.3 Synthesis 17
2.4 ModeofAction 21
2.5 Structure–ActivityRelationships 22
References 25
3 AnalgesicandAnestheticAmides 27
ThomasErhard
3.1 Introduction 27
3.2 History 27
3.3 Synthesis 30
VI Contents
3.4 ModeofAction 33
3.5 Structure–ActivityRelationships 34
References 37
PartII CardiovascularDiseases 39
4 FibrateAcidsandEstersfortheTreatmentofHyperlipidemia
(PPAR𝛂Activators) 41
GavinO’Mahony
4.1 Introduction 41
4.2 History 42
4.3 Synthesis 45
4.4 ModeofAction 48
4.5 Structure–ActivityRelationships 50
References 54
5 Antiplatelet2-HydroxyThienopyridineEsterDerivativesforthe
ReductionofThromboticCardiovascularEvents 57
ModestodeCandia,NunzioDenora,andCosimoD.Altomare
5.1 Introduction 57
5.2 History 57
5.3 Synthesis 60
5.4 ModeofAction 62
5.5 Structure–ActivityRelationships 67
References 70
6 CarboxylicAcidsandLactonesasHMG-CoAReductase
Inhibitors 71
Xiang-YangYeandPratikDevasthale
6.1 Introduction 71
6.2 History 72
6.3 Synthesis 73
6.4 ModeofAction 80
6.5 Structure–ActivityRelationship 81
References 83
7 AngiotensinIIReceptorAntagonistswithCarboxylicFunctionalitiesin
CardiovascularDisease 87
SteveSwannandSimoneBigi
7.1 Introduction 87
7.2 History 89
7.3 Synthesis 90
7.4 ModeofAction 95
Contents VII
7.5 Structure–ActivityRelationships 96
References 99
8 CarboxylicAcidContainingDirectThrombinInhibitorsforthe
TreatmentofThromboembolicDiseases 103
HarryR.ChobanianandMathewM.Yanik
8.1 Introduction 103
8.2 History 104
8.3 Synthesis 106
8.4 ModeofAction 108
8.5 Structure–ActivityRelationship 109
References 113
PartIII InfectiousDiseases 115
9 TetracyclineAmideAntibiotics 117
IngoJanser
9.1 Introduction 117
9.2 History 120
9.2.1 First-GenerationTetracyclines–TheDiscovery 120
9.2.2 Second-GenerationSemisyntheticTetracyclines 121
9.2.3 TetracyclineResistance 122
9.2.4 Third-GenerationTetracyclines 123
9.3 Synthesis 123
9.4 ModeofAction 127
9.5 Structure–ActivityRelationships 128
References 130
10 Carboxylic-Acid-BasedNeuraminidaseInhibitors 133
StacyVanEpps
10.1 Introduction 133
10.2 History 133
10.3 Synthesis 136
10.4 ModeofAction 142
10.5 Structure–ActivityRelationships 143
References 146
11 OxazolidinoneAmideAntibiotics 149
CristianaA.Zaharia,SaverioCellamare,andCosimoD.Altomare
11.1 Introduction 149
11.2 History 150
11.3 Synthesis 153
11.4 MechanismofAction 156
11.5 Structure–ActivityRelationships 162
References 164
VIII Contents
12 Sovaldi,anNS5BRNAPolymerase-InhibitingCarboxylicAcidEster
UsedfortheTreatmentofHepatitisCInfection 167
AlastairDonald
12.1 Introduction 167
12.2 History 168
12.3 Synthesis 170
12.4 ModeofAction 172
12.5 Structure–ActivityRelationships 173
References 174
PartIV MetabolicDiseases 177
13 DipeptidylPeptidase-4(DPP-4)-InhibitingAmidesfortheTreatmentof
Diabetes 179
NaomiS.RajapaksaandXiaodongLin
13.1 Introduction 179
13.2 History 179
13.3 Synthesis 184
13.4 ModeofAction 187
13.5 Structure–ActivityRelationships 188
References 193
PartV Oncology 197
14 Ibrutinib,aCarboxylicAcidAmideInhibitorofBruton’sTyrosine
Kinase 199
TimothyD.Owens
14.1 Introduction 199
14.2 History 199
14.3 Synthesis 201
14.4 MechanismofAction 202
14.5 Structure–ActivityRelationships 203
References 207
PartVI Anti-InflammatoryDrugs 209
15 FumaricAcidEsters 211
TonyS.Gibson
15.1 Introduction 211
15.2 History 211
15.3 Synthesis 213
15.4 ModeofAction 213
15.5 Structure–ActivityRelationships 215
References 218