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11 Thiazole: A privileged scaffold in drug discovery 279
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Index
Symbols
3D QSAR (quantitative structure-activity
re
lationships) 24
α-carbon hydroxylation via carbinolamine
pathway 125
α-substituents determining carbon or nitrogen
oxidations 129
– Primary aliphatic amines 130
ω–1 oxidation 122
ω-oxidation 122
A
Acetylation 154
acetylation polymorphism 155
Achiral drugs 141
activated enzyme complex 113
Aflatoxin B1 exhibiting biotoxification via
epoxide metabolite 119
Age 157
Aldo-keto reductases 140
alicyclic hydroxylation 123
Alicyclic tertiary amines 127
– N-dealkylation of t-butyl groups 127
Aliphatic and alicyclic amines 125
– Bis-dealkylation 125
– cyclization reaction 125
amine oxidases 124
Angiogenesis 168
anticancer 168
antipsychotics 191
anti-schizophrenic 183
arenol metabolites 117
B
binding site 20
Bioinformatics 16
butyrophenone drugs 189
– benperidol 190
– bromperidol 190
– droperidol 190
– trifluperidol 190
C
Catalytic reaction cycle of cytochrome P450
monooxygenases 112
Cellular toxicity of bromobenzene 118
cheminformatics 16
cheminformatics databases 26
chiral ketones 142
– α, β-unsaturated ketones 142
chizophrenia etiology, diagnosis and
treatment 194
– cranial neuroimaging 194
– deep brain stimulation (DBS) 194
– guidelines to improve clinical practice 195
– information campaigns 194
– new drugs 194
– psychotherapy 194
– repetitive transcranial magnetic stimulation
(rTMS) 194
– specialized healthcare professionals 195
chlorpromazine 184
clinical development 23
clozapine 185
Cluster analysis 200
Cluster membership 208
CoMFA (Comparative Molecular Field Analysis) 25
Commiphora wightii 201
complementary and alternative medicine
(CAM) 173
Computational tools 18
CoMSIA (Comparative Molecular Similarity Index
Analysis) 25
Conjugated products 149
– Aryl acids 149
– arylaliphatic acids 149
Conjugation with glycine, glutamine, and other
amino acids 151
Cytochrome P450 catalyzed reactions 114
Cytochrome P450 monooxygenases 111
cytotoxicity 168
D
Dendrogram 205
destruction of cytochrome P450 via epoxide
formation 120
Detoxification of arene oxide via enzymatic
hydration 117
Detoxification of Δ1-THC 110
dibenzodiazepine 191
– Clozapine 191
Dibenzodiazepine 192
Dibenzothiazepine 192
– quetiapine 192
284 Index
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Dibenzoxazepine 192
diphenylbutylpiperidines drugs 190
“dopamine hypothesis” 185
drug designing 16
– de novo drug designing 22
– ligand-based drug designing 17
– structure-based drug designing 17
drug development 15
drug-receptor interactions 15
Drug target identification 18
drug targets 20
E
Effect of substituents on aromatic hydrox-
ylation 115
eigen v
alues 208
Environmental pollutants 116
Enzyme induction 158
Enzyme inhibition 159
F
Factors affecting drug metabolism 156
Fate of arene oxide 116
– “NIH shift” 117
G
Glucuronic acid conjugation 148
Glucuronidation 148
Glutamine conjugation 152
glycine conjugation 151
– Carboxylic acid metabolites 151
GSH or mercapturic acid conjugates 152
H
Haloperidol 189
Hereditary factors 158
Hierarchical clustering analysis 204
High-Throughput Screening 21
Hydrolysis of esters and amides 145
– ester hydrolysis 145
Hydrolytic reactions 145
I
immunomodulation 173
Inducing agents 158
industrial chemicals 153
Inhibitors of hepatic microsomal epoxide
hydrase 118
Iscador 166
L
lactam metabolites 128
optimization 22
lead
Lectins 166
M
major tranquillizers 183
mental
disorders 183
Metabolic aromatization 137
Metabolism 107
Metabolism of aromatic amines 130
– “methemoglobin” or “ferrrihemoglobin” 132
– N-Oxidation of primary aromatic amines 131
Methylation 155
Miscellaneous hydrolytic reactions 147
Miscellaneous reductions 144
Mistletoes 165
Mixed-function oxidases or monooxy-
genases 111
Molecular docking 21
N
N-acetylation 154
N-Acetyltransferase enzymes 154
N-acyltransferase enzymes 151
N-dealkylation of 2° amines and 1° amines 128
– Direct deamination of 2° amine 129
– Metabolic N-oxidation of 2° aliphatic and
alicyclic amines 129
neuroleptics 183
O
Olanzapine 193
O-methylation 156
Oxidation at aliphatic and alicyclic carbon
atoms 122
Oxidation at allylic carbon atoms 121
Oxidation at benzylic carbon atom 120
Oxidation at carbon atoms α to carbonyls and
imines 121
Oxidation involving C-O bonds 133
Oxidation involving C-S bonds 134
– S-dealkylation, desulfuration and
S-oxidation 134
Oxidation of alcohols and aldehydes 136
– Aldehyde metabolites 136
Oxidation of amides 132
– cyclic amides or lactams 133
Oxidation of aromatic moieties 114
– Aromatic hydroxylation 114
Index 285
Oxidation of carbon-heteroatom bonds 124
– hydroxylation or oxidation of heteroatom 124
– Oxidative removal of alkyl groups 124
Oxidation of olefins 118
– epoxide metabolites 118
Oxidation of primary and secondary
alcohols 136
– alcohol dehydrogenases 137
Oxidations involving C-N systems 124
oxidative dehalogenation 137
Oxidative mechanisms 114
oxidative N-dealkylation 125
Oxidoreductase enzymes 140
P
Pearson Correlation 206
Pharm
acodynamic tests 23
Pharmacokinetic tests 23
pharmacophore modeling 24
Phase II conjugation reactions 148
– conjugating group 148
Phase II reactions 109
Phase I metabolism 108
– Phase I metabolites 109
phenothiazine 183
Phenothiazine types 188
– Aliphatic 188
– Piperazine 188
– Piperidine 188
Pimozide 190
preferential aromatic hydroxylation 116
Principal component analysis 200
principal component score 212
“product stereoselectivity” 141
Psychosis 184
psychotic illness 184
R
Reduction of aldehydes and ketones 139
Reduction of
Reduction of N-oxides 144
Reduction of sulfur 145
Reductive reactions 139
ribosome inactivating proteins (RIPs) 170
Risperidone 193
Rotated component matrix 210
S
schizophrenia 184
Scr
ee plot 208
211
Sex differences 158
– gender differences 158
S-glucuronide conjugates 150
Similarity analysis 202
Sites of drug biotransformation 110
Species and strain differences 157
– Species variation 157
– Strain differences 157
Sulfate conjugation 150
T
The three-dimensional 19
Thiothixene 189
thioxanthene 189
triterpenoids 166
V
variance matrix 210
varimax rotation 203
viscotoxins 165
X
X-ray crystallography 19
nitro and azo compounds 143
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