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11 Experimenteller Teil
257
11.14.11.15 Herstellung von N’-(4-(2-Oxo-2H-chromen-3-yl)thiazol-2-yl)-2-
naphthohydrazid (308)
6
1
10
9
8
7
N
H
11
O
H
N
12
13
S
15
14
N
16
5
4
3
2
O
23
18
17
22
21
20
19
O
Nach Umkristallisation aus EE werden 105 mg (51%) von
N’-(4-(2-Oxo-2H-chromen-
3-yl)thiazol-2-yl)-2-naphthohydrazid
308 als gelber Feststoff erhalten.
1
H-NMR (300 MHz, DMSO-d
6
):
δ
= 11.12 (s, 1H, 11-NH), 9.84 (s, 1H, 10-NH), 8.59
(
s, 1H, 17-H), 8.57 (s, 1H, 7-H), 8.10–8.00 (m, 4H, 2-H, 9-H, 10-H), 7.87 (d, 1H, 19-
H, J = 7.1 Hz), 7.74 (
s, 1H, 15-H), 7.66–7.60 (m, 3H, 3-H, 4-H, 21-H), 7.44 (d, 1H,
22-H, J = 8.2 Hz), 7.38 (
t, 1H, 20-H, J = 7.3 Hz) ppm.
13
C-NMR (75 MHz, DMSO-d
6
):
δ
= 172.9 (13-C), 167.4 (CONR), 159.4 (COOR),
153.0 (14-C), 144.8 (23-C), 139.1 (17-C), 135.2 (6-C), 132.7 (8-C), 132.3 (5-C),
130.3 (1-C), 129.7 (7-C), 129.5 (3-C), 129.0 (10-C), 128.8 (2-C), 128.4 (4-C), 127.7
(19-C), 125.4 (20-C), 124.5 (9-C), 121.1 (16-C), 119.9 (18-C), 116.5 (22-C), 110.7
(15-C) ppm.
11.14.11.16 Herstellung von N’-(4-Phenylthiazol-2-yl)benz[d][1,3]dioxol-5-
carbhydrazid (309)
2
3
7
6
5
4
N
H
8
O
H
N
9
10
S
12
11
N
13
16
15
14
O
1
O
Nach Umkristallisation aus EE werden 111 mg (58%) von
N’-(4-Phenylthiazol-2-
yl)benz[
d][1,3]dioxol-5-carbhydrazid 309 als violetter Feststoff erhalten.
1
H-NMR (300 MHz, DMSO-d
6
):
δ
= 10.74 (s, 1H, 8-NH), 9.62 (s, 1H, 9-NH), 7.84 (d,
2H, 14-H, J = 7.3 Hz), 7.53 (
dd, 1H, 6-H, J = 1.4, 8.1 Hz), 7.44–7.36 (m, 3H, 4-H, 16-
- Danksagung 3
- Inhaltsverzeichnis 5
- 11 EXPERIMENTELLER TEIL 163 8
- 12 LITERATURVERZEICHNIS 294 14
- Abbildungsverzeichnis 15
- Verzeichnis der Schemata 18
- Verzeichnis der Tabellen 19
- Abkürzungen und Akronyme 20
- Verzeichnis der Aminosäuren 23
- 1.3 Risikofaktoren 29
- 1.5.1 Der APP-Metabolismus 33
- 1.5.2 Aspartylproteasen 37
- 1-Aktivität (IC 45
- 1. Es konnten keinerlei 45
- [119,120] 52
- [130-132] 54
- [133-137] 54
- [139,140] 54
- [141-143] 54
- [136,137] 55
- Reduzierende Bedingungen 56
- Oxidierende Bedingungen 56
- [146,147] 57
- Superoxid↑ 63
- [180,181] 64
- 2 Wirkstoffdesign 65
- [186,187] 69
- [189,190] 69
- [194,195] 71
- [196,197] 72
- 2.4 Pharmakokinetik 74
- [209,210] 75
- Inhibitoren 80
- [224-229] 84
- [228,230] 84
- [233-235] 91
- Akzeptor 96
- Emission 97
- Anregung 97
- 1 bilden. Für 101
- 1. Zur Verfügung 102
- Asparaginsäureaktivierung 103
- Terminus 107
- 5.3 Synthese 108
- Sekretase-Inhibitors 115
- 6.2 Syntheseplan 116
- 6.3 Synthese 118
- 7.1 Einleitung 120
- 7.3 Synthese 122
- 7.4 Biologische Aktivität 124
- Aβ-Gehalt [%] 125
- (% control ± SD) 126
- = cell death 127
- Gehalt [%] 128
- 200-203 geschehen ist 130
- 8.1 Einleitung 131
- Screening mit CATALYST 132
- Screening 134
- 8.3 Algorithmen in CATALYST 136
- Poling-Funktion genannt 140
- 5.3)MAlog()Alog( > 143
- 1. Generation der 144
- 5.3)MAlog()Alog( >− 146
- -feature 148
- 9.1 Einleitung 155
- 235), bei denen in ersten 156
- 256 ins Auge gefasst. Sie 156
- 9.3 Synthese 159
- Ausbeuten 160
- 370 (Schema 169
- 9.4 Biologische Aktivität 173
- 10 Zusammenfassung 182
- 10.3 γ-Sekretase-Inhibitoren 184
- 10.4 Inhibition von GSK3β 185
- 10.5 Tau-Inhibitoren 186
- 11 Experimenteller Teil 187
- Bromacetamide 86-89 189
- N HCl-Lsg 190
- Tetramsäuren 43-85 196
- Tetronsäuren 95-100 223
- N HCl-Lsg. (3 x 30 237
- 11.9 Synthese von DAPT (13) 243
- Derivate 149-153 245
- N HCl-Lsg. (3 x 30 mL), 0.1N 246
- DAPT-Derivats 152 250
- N HCl-Lsg. (3 x 10 mL) 253
- N HCl-Lsg. (3 x 20 253
- 200-203 255
- 346/347 297
- 12 Literaturverzeichnis 318
- Lebenslauf 329
- Veröffentlichungen 331
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