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Section A-The science of medicinal chemistry 1

A1 Introduction 1

A2 From concept to market 4

Section B-Drug targets 7

B1 Enzymes 7

B2 Receptors 13

B3 Carrier proteins 24

B4 Structural proteins 27

B5 Nucleic acids 29

B6 Lipids 35

B7 Carbohydrates 38

Section C-Pharmacokinetics 41

C1 Pharmacokinetics 41

C2 Drug absorption 42

C3 Drug distribution 45

C4 Drug metabolism 48

C5 Drug excretion 51

C6 Drug administration 54

C7 Drug dosing 58

Section D-Biological testing and bioassays 61

D1 Testing drugs 61

D2 Testing drugs in vitro 62

D3 Testing drugs in vivo 70

Section E-Drug discovery 75

E1 The lead compound 75

E2 Natural sources of lead compounds 77

E3 Synthetic sources of lead compounds 82

F1 Synthetic considerations 85

Section F-Synthesis 85

F2 Stereochemistry 90

F3 Combinatorial synthesis 100

Section G-Structure-activity relationships 105

G1 Definition of structure-activity relationships 105

G2 Binding interactions 107

G3 Functional groups as binding groups 110

G4 The pharmacophore 120

G5 Quantitative structure-activity relationships 125

H1 Aims of drug design 141

Section H-Target orientated drug design 141

H2 Computer aided drug design 143

H3 Simplification of complex molecules 148

H4 Conformational restraint 151

H5 Extra binding interactions 155

H6 Enhancing existing binding interactions 160

Section I-Pharmacokinetic orientated drug design 167

I1 Drug solubility 167

I2 Drug stability 171

J1 Patenting and chemical development 177

Section J-Patenting and manufacture 177

J2 Optimization of reactions 181

J3 Scale-up issues 188

J4 Process development 193

J5 Specifications 197

Section K-Preclinical testing and clinical trials 203

K1 Toxicology 203

K2 Pharmacology and pharmaceutical chemistry 205

K3 Drug metabolism studies 207

K4 Clinial trials 212

K5 Regulatory affairs 216

Section L-Case study：inhibitors of EGF-receptor kinase 221

L1 Epidermal growth factor receptor 221

L2 Testing procedures 224

L3 From lead compound to dianilino-phthalimides 226

L4 Modeling studies 233

L5 4-(Phenylamino)pyrrolopyrimidines 239

L6 Pyrazolopyrimidines 241

Section M-History of medicinal chemistry 245

M1 The age of herbs,potions and magic 245

M2 The nineteenth century 247

M3 A fledgling science(1900-1930) 251

M4 The dawn of the antibacterial age(1930-1945) 254

M5 The antibiotic age(1945-1970s) 258

M6 The age of reason(1970s to present) 266

Further reading 271

Index 273