Neuartige (S)-2,3-Oxidosqualencyclase-Inhibitoren:
Gespeichert in:
| 1. Verfasser: | |
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| Format: | Buch |
| Sprache: | German |
| Veröffentlicht: |
München
Verl. Dr. Hut
2006
|
| Ausgabe: | 1. Aufl. |
| Schriftenreihe: | Pharmazeutische Chemie
|
| Schlagworte: | |
| Online-Zugang: | Inhaltsverzeichnis |
| Beschreibung: | Zugl.: München, Univ., Diss., 2006 |
| Beschreibung: | 245 S. Ill., graph. Darst. 210 mm x 148 mm, 343 gr. |
| ISBN: | 9783899633856 3899633857 |
Internformat
MARC
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| 100 | 1 | |a Lange, Stefanie |e Verfasser |4 aut | |
| 245 | 1 | 0 | |a Neuartige (S)-2,3-Oxidosqualencyclase-Inhibitoren |c Stefanie Lange |
| 250 | |a 1. Aufl. | ||
| 264 | 1 | |a München |b Verl. Dr. Hut |c 2006 | |
| 300 | |a 245 S. |b Ill., graph. Darst. |c 210 mm x 148 mm, 343 gr. | ||
| 336 | |b txt |2 rdacontent | ||
| 337 | |b n |2 rdamedia | ||
| 338 | |b nc |2 rdacarrier | ||
| 490 | 0 | |a Pharmazeutische Chemie | |
| 500 | |a Zugl.: München, Univ., Diss., 2006 | ||
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| 650 | 0 | 7 | |a Cyclasen |0 (DE-588)4468848-9 |2 gnd |9 rswk-swf |
| 655 | 7 | |0 (DE-588)4113937-9 |a Hochschulschrift |2 gnd-content | |
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| 689 | 0 | 1 | |a Cyclasen |0 (DE-588)4468848-9 |D s |
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Datensatz im Suchindex
| _version_ | 1804135604949090304 |
|---|---|
| adam_text | Inhaltsverzeichnis
1. Einleitung 1
1.1 Triterpenbiosynthese 3
1.1.1 Der Präsqualen Abschnitt 3
1.1.2 Der Postsqualen Abschnitt 5
1.1.3 Die Oxidosqualencyclasen 5
1.1.3.1 Bildung des A Rings 6
1.1.3.2 Bildung des B und des C Rings 7
1.1.3.3 Bildung des Protosterolkations und Umlagerung zu Lanosterol 7
1.1.4 Die Squalen Hopen Cyclasen 8
1.2 Oxidosqualencyclase Inhibitoren als Antimykotika 10
1.2.1 Angriffspunkte bekannter Ergosterol Biosynthese Inhibitoren 10
1.2.2 Die Allylamine 11
1.2.3 Die Azole 12
1.2.4. Morpholine 12
1.2.5 High Energy Intermediate Analoga 13
1.2.5.1 Azasqualene 14
1.2.5.2 Monocyclische Aminoalkyl Derivate 15
1.2.5.3 Bicyclische Aminoalkyl Derivate 16
1.2.5.4 Protosterol HEI Analoga 16
1.2.5.5 Weitere Antimykotika 17
1.3 Oxidosqualencyclase Inhibitoren als Lipidsenker 18
1.4 Oxidosqualencyclase Inhibitoren als Antiprotozoenmittel 23
2. Themenstellung und Syntheseplanung 26
2.1 Themenstellung 26
2.2 Syntheseplanung 28
2.2.1 Imitate des carbokationischen C 2 HEI 28
2.2.2 Imitate des carbokationischen pro C 10 HEI 28
2.2.3 Tricyclische Derivate: Annellierung eines B Ring Äquivalents 29
3. Synthesen 31
3.1 Der Grundkörper: Windaus Keton 31
3.2 Aminoalkyl Derivate 33
3.2.1 WiWg neaMon 33
3.2.2 Gnöna/d Reaktionen 34
Inhaltsverzeichnis
3.2.3 Aminierungen des Halogenalkyl Derivates 33 36
3.2.4 CaccW Kupplung 41
3.3. Aminoalkylether Derivate 44
3.3.1 WW/amso/vEthersynthese 44
3.4 Aminoalkylamino Derivate 46
3.4.1 Reduktive Aminierungen 46
3.4.1.1 Analytik der Verbindungen 58 und 59 50
3.5 Aminoalkylamid Derivate 54
3.5.1 Umesterung 55
3.5.2 Gerüstumlagerung 57
3.5.3 O Alkylierung unter Rhodium(ll) Katalyse 58
3.6 a Aminoketone 65
3.6.1 a Derivatisierung von Windaus Keton 66
3.6.2 Aminierungen des a Bromketons 69
3.7 Aminoalkohol Derivate 73
3.8 Tricyclische Derivate: Annellierung eines B Ring Äquivalents 74
3.8.1 Die SWfe Kupplung 74
3.8.2 D/e/s /l/cte/ Cycloadditionen 76
3.8.3 Weitere B Ring Synthesen 83
3.8.3.1 Annellierung fünfgliedriger Heterocyclen 84
4. Biologische Prüfung 89
4.1 Agar Diffusionstest 89
4.1.1 Testergebnisse 89
4.2 Test auf Inhibition der Ergosterolbiosynthese 97
4.3 Test auf Inhibition der Oxidosqualencyclasen 97
4.4 Allgemeine Struktur Aktivitäts Beziehungen 104
4.4.1 Inhibition der fungalen OSC 105
4.4.2 Inhibition der protozoischen OSC 106
4.4.4 Inhibition der herbaten OSC 107
4.4.5 Inhibition der humanen OSC 107
4.5MTT Test 108
5. Zusammenfassung 111
6. Experimenteller Teil 122
6.1 Geräte und Parameter 122
Inhaltsverzeichnis
6.2 Beschreibung der Substanzen 124
(1 fl,3afl,7afl) 4 Cyclopropyl 1 [(fl) 1,5 dimethylhexyl] 7a methyl octahydro
inden 4 ol (32) 124
(1 fl,7afl) 4 (3 Brompropyl) 2,3,5,6,7,7a hexahydro 7a methyl 1 [(fl) 1,5
dimethylhexyl] 1 H inden (33) 126
A/ Allyl A/ Methyl {3 [(1 fl,7afi) 1 [(fl) 1,5 dimethylhexyl] 7a methyl
2,3,5,6,7,7a hexahydro 1H inden 4 yl] propyl} amin (35) 128
N Methyl {3 [(1 fl,7afl) 1 [(fl) 1,5 dimethylhexyl] 7a methyl 2,3,5,6,7,7a
hexahydro 1H inden 4 yl] propyl} amin (36) 130
A/,/V Dimethyl {3 [(1 R,7afl) 1 [(fl) 1,5 dimethylhexyl] 7a methyl 2,3,5,6,7,7a
hexahydro 1H inden 4 yl] propyl} methylamin (37) 132
1 {3 [(1 fl,7afi) 1 [(H) 1 .S Dimethylhexyll^a methyl a.S.ö.ejJa hexahydro
1 W inden 4 yl] propyl} piperidin (38) 134
4 {3 [(1 fl,7afl) 1 [(fl) 1,5 Dimethylhexyl] 7a methyl 2,3,5,6,7,7a hexahydro
/W inden 4 yl] propyl} morpholin(39) 136
1 {3 [(1 R,7afl) 1 [(fl) 1,5 Dimethylhexyl] 7a methyl 2,3,5,6,7,7a hexahydro
1H inden 4 yl] propyl} pyridiniumbromid (40) 138
N,A/ Dimethyl {3 [(1 fl,7afl) 1 [(fl) 1,5 dimethylhexyl] 7a methyl 2,3,5,6,7,7a
hexahydro 1H inden 4 yl] propyl} amin A/ oxid(41) 140
(1 R,3aflS,4flS,7afl) 4 (3 Brompropyl) octahydro 7a methyl 1 [(R) 1,5
dimethylhexyl] 1 H inden (42a/b) 142
A^AIIyl {3 [(1 R,3aflS,4flS,7afl) 1 [(fl) 1,5 dimethylhexyl] 7a methyl
octahydro 1 W inden 4 yl] propyl} methylamin (43a/b) 144
(Isomeren Gemisch) 144
Trifluormethansulfonsäure {(1R,3afl,7afl) 1 [(fl) 1,5 dimethylhexyl] 7a methyl
2,3,3a,6,7,7a hexahydro 1H inden 4 yl} ester(44) 146
2 {(1 fl,3afl,7aR) 1 [(fl) 1,5 Dimethylhexyl] 7a methyl 2,3,3a,6,7,7a
hexahydro 1 H inden 4 ylethinyl} pyridin (45) 148
(1 fl,3afl,4S,7afl) 1 [(fl) 1,5 Dimethylhexyl] 7a methyl octahydro inden 4 ol
(47) 150
2 [(1 fl,3a/?,4S,7afl) 1 [(fl) 1,5 Dimethylhexyl] 7a methyl octahydro inden 4
yloxymethyl] pyridin (48) 152
2 [(1 fl,3afl,4S,7afl) 1 [(fl) 1,5 Dimethylhexyl] 7a methyl octahydro inden 4 yl
oxymethyn 1 methyl pyridiniumioclid(49) 154
Inhaltsverzeichnis
/V {(1 ft,3aflS,4RS,7afl) 1 [(fi) 1,5 Dimethylhexyl] 7a methyl octahydro inden
4 yl} A/,/Vkümethyl ethan 1,2 diamin(50) 156
A/ Methyl {(1 fl,3aft,4S,7afl) 1 [(fl) 1,5 Dimethylhexyl] 7a methyl octahydro
inden 4 yl} amin (51) 158
{(1 R,3afi,4S,7afi) 1 [(fl) 1,5 Dimethylhexyl] 7a methyl octahydro inden 4 yl}
(2 piperidin 1 yl ethyl) amin (53) 160
{(1 f?,3afl,4S,7afl) 1 [(fl) 1,5 Dimethylhexyl] 7a methyl octahydro inden 4 yl}
(2 pyrrolidin 1 yl ethyl) amin (54) 162
{(1 fl,3afl,4S,7afl) 1 [(fl) 1,5 Dimethylhexyl] 7a methyl octahydro inden 4 yl}
(2 morpholin 4 yl ethyl) amin(55) 164
{(1 fl,3afl,4S,7afl) 1 [(R) 1,5 Dimethylhexyl] 7a methyl octahydro inden 4 yl}
1 (1W imidazol 1 yl propyl) amin (56) 166
{(1 fl,3afl,4S,7afl) 1 [(fl) 1,5 Dimethylhexyl] 7a methyl octahydro inden 4 yl}
pyridin 2 ylmethylamin (57) 168
N {(1 fl,3afl,4S,7aR) 1 [(fl) 1,5 Dimethylhexyl] 7a methyl octahydro inden 4
yl]} A^methyl (pyridin 2 ylmethyl) amin (58) 170
A/ {(1 ff,3aS,4S,7afl) 1 [(R) 1,5 Dimethylhexyl] 7a methyl octahydro inden 4
yl]} W methyl (pyridin 2 ylmethyl) amin(59) 172
A/ (2 Dimethylamino ethyl) 2 [(1 fl,3afl,4S,7afl) 1 (1,5 dimethylhexyl) 7a
methyl octahydro inden 4 yloxy] W methyl acetamid (61) 174
Bromessigsäure[(1 R,3aR,4S,7aR) 1 (1,5 dimethylhexyl) 7a methyl octahydro
inden 4 yl] ester (62) 176
2 [A/ ( Dimethylaminoethyl) W methyl amino] essigsäure[(1R,3a/:?,4S,7afi) 1
(1,5 dimethyl hexyl) 7a methyl octahydro inden 4 yl] ester (63) 178
(3aS) 1 [(R,S) 1,5 Dimethylhexyl] 3a methyl 2,3,3a,4,5,6,7 hexahydro 2H
inden(64a/b) 180
{(1 R,3afl,4S,7afl) 1 [(fl)1,5 Dimethylhexyl] 7a methyl octahydro inden 4
yloxyj essigsäureethylester (65) 182
[(1 fl,3aft,4S,7afl) 1 (1,5 Dimethylhexyl) 7a methyl octahydro inden 4 yloxy]
essigsäure (66) 184
2 {(1 fl,3afl,4S,7a/?) 1 [(fl) 1,5 Dimethylhexyl] 7a methyl octahydro inden 4
yloxy] 1 (4 methyl piperazin 1 yl) ethanon (67) 186
{(1 fl,3afi,4S,7afl) 1 [(fl) 1,5 Dimethylhexyl] 7a methyl octahydro inden 4
yloxy} 1 (4 methyl [1,4]diazepan 1 yl) ethanon(68) 188
Inhaltsverzeichnis
(1 fl,7afl) 3a Brom 7a methyl 1 [(fl) 1,5 dimethylhexyl] octahydro inden 4 on
(69) 190
(1 ft,3afi,5f?,7afl) 5 Brom 7a methyl 1 [(fl) 1,5 dimethylhexyl] octahydro
inden 4 on (70) 191
{(1 R,3aR,7aR) 1 [(fl) 1,5 Dimethylhexyl] 7a methyl 2,3,3a,6,7,7a hexahydro
1W inden 4 yloxy} trimethylsilan(71) 193
(1 fl,3afiS,5flS,7afl) 5 (/V Allyl A/ methyl amino) 1 [(fl) 1,5 dimethylhexyl] 7a
methyl octahydro inden 4 on (72) 195
(1 R,3aRS,5RS,7aR) 5 N, A/ Dimethylamino 1 [(fl) 1,5 dimethylhexyl] 7a
methyl octahydro inden 4 on (73) 197
(1 fl,3aflS,5flS,7afl) 1 [(fl) 1,5 Dimethylhexyl] 7a methyl 5 (4 methyl
piperazin 1 yl) octahydro inden 4 on (74) 199
(1 fl,3aflS,5flS,7afl) 1 [(R) 1,5 Dimethylhexyl] 7a methyl 5 (piperidin 1 yl)
octahydro inden 4 on (75) 201
(1 fl,3aflS,5RS,7afl) 1 [(fl) 1,5 Dimethylhexyl] 5 (2,6 dimethylmorpholin 4 yl)
7a methyl octahydro inden 4 on (76) 203
(1 R,3aflS,5RS,7afl) 1 [(R) 1,5 Dimethylhexyl] 5 (4 hydroxy piperidin 1 yl) 7a
methyl octahydro inden 4 on (77) 205
(1 R,7aR)A [(H) 1,5 Dimethylhexyl] 7a methyl 4 methylamino 1,2,3,6,7,7a
hexahydro inden 5 on (80) 207
(1 ft,3aflS,4flS,5flS,7afl) 5 Dimethylamino 1 [(R) 1,5 dimethylhexyl] 7a
methyl octahydro inden 4 ol (81) 209
(1 fl,3aflS,5f?S,7afl) 1 [(fl) 1,5 Dimethylhexyl] 7a methyl 5 (4 methyl
piperazin 1 yl) octahydro inden 4 ol(82) 211
(1 fl,3afl,7afl) 2,3,3a,6,7,7a Hexahydro 7a methyl 1 [(fl) 1,5 dimethyl hexyl)
4 vinyl 1 H inden (83) 213
(4aflS,6afi,7fi,9af?) 7 [(R) 1,5 Dimethylhexyl] 6a methyl 2,5,6,6a,7,8,9,9a
octahydro 4aH cyclopenta[/]cinnolin 3,4 dicarbonsäurediethylester 215
(84) 215
(4aflS,6aR,7f?,9afl) 7 [(fl) 1,5 Dimethylhexyl] 6a methyl 2,5,6,6a,7,8,9,9a
octahydro 4a/+cyclopenta[qcinnolin 3,4 dicarbonsäurediisopropylester (85)
217
(4a/?,6afl,7fl,9afl) 7 [(fl) 1,5 Dimethylhexyl] 3,4,6a trimethyl
2,4,4a,5,6,6a,7,8,9,9a decahydro 3H ^ck penlal/|cinnolin(86) 219
Inhaltsverzeichnis
(4aS,6afl,7R,9afl) 7 [(fl) 1,5 Dimethylhexyl] 3,4,6a trimethyl
2,4,4a,5,6,6a,7,8,9,9a decahydro 3« cyclopenta[f]cinnolin (87) 219
(5S,8S,9fl,10S,14fl) 17 [(fl) 1,5 Dimethylhexyl] 14 methyl
2,3,4,5,6,7,8,9,10,11,12,14,15,16 tetradecahydro cyclopenta[a]phenantren 1
on(89) 222
{(3R,3aR,9bfl) 3 [(fl) 1,5 Dimethylhexyl] 3a methyl 2,3,3a,4,5,9b hexahydro
1 H 7,9 diaza cyclopenta[a]naphthalen 8 yl} amin (90) 224
{(3f?,3afl,9bR) 3 [(fl) 1,5 Dimethylhexyl] 3a methyl 2,3,3a,4,5,9b hexahydro
1H 7,9 diaza cyclopenta[a]naphtalen 8 yl} methylamin(91) 226
(1 fi,7afl) 1 [(fl) 1,5 Dimethylhexyl] 4 hydroxy 7a methyl 1,2,3,6,7,7a
hexahydro inden 5 on (92) 228
(5afi,6fl,8aflS) 6 [(fl) 1,5 Dimethylhexyl] 5a methyl 5,5a,6,7,8,8a hexahydro
4H 1 aza 3 thia as indacen 2 ylamin (93a/b) 230
A/ {(5afl,6R,8afi) 6 [(fi) 1,5 Dimethylhexyl] 5a methyl 5,5a,6,7,8,8a
hexahydro 4/+1 aza 3 thia as indacen 2 yl} guanidin (94) 232
6.3 Testmethoden der biologischen Prüfung 234
6.3.1 Agardiffusionstest 234
6.3.2 Ergosterol Biosynthese Inhibitoren 235
6.3.3 OSC Aktivität und Inhibition 235
6.3.3.1 Stämme von S. cerevisiae und Kulturbedingungen 236
6.3.3.2 Enzym Assay 236
6.3.4 MTT Test 238
7. Verzeichnis der Abkürzungen 239
8. Literaturverzeichnis 242
|
| adam_txt |
Inhaltsverzeichnis
1. Einleitung 1
1.1 Triterpenbiosynthese 3
1.1.1 Der Präsqualen Abschnitt 3
1.1.2 Der Postsqualen Abschnitt 5
1.1.3 Die Oxidosqualencyclasen 5
1.1.3.1 Bildung des A Rings 6
1.1.3.2 Bildung des B und des C Rings 7
1.1.3.3 Bildung des Protosterolkations und Umlagerung zu Lanosterol 7
1.1.4 Die Squalen Hopen Cyclasen 8
1.2 Oxidosqualencyclase Inhibitoren als Antimykotika 10
1.2.1 Angriffspunkte bekannter Ergosterol Biosynthese Inhibitoren 10
1.2.2 Die Allylamine 11
1.2.3 Die Azole 12
1.2.4. Morpholine 12
1.2.5 High Energy Intermediate Analoga 13
1.2.5.1 Azasqualene 14
1.2.5.2 Monocyclische Aminoalkyl Derivate 15
1.2.5.3 Bicyclische Aminoalkyl Derivate 16
1.2.5.4 Protosterol HEI Analoga 16
1.2.5.5 Weitere Antimykotika 17
1.3 Oxidosqualencyclase Inhibitoren als Lipidsenker 18
1.4 Oxidosqualencyclase Inhibitoren als Antiprotozoenmittel 23
2. Themenstellung und Syntheseplanung 26
2.1 Themenstellung 26
2.2 Syntheseplanung 28
2.2.1 Imitate des carbokationischen C 2 HEI 28
2.2.2 Imitate des carbokationischen pro C 10 HEI 28
2.2.3 Tricyclische Derivate: Annellierung eines B Ring Äquivalents 29
3. Synthesen 31
3.1 Der Grundkörper: Windaus Keton 31
3.2 Aminoalkyl Derivate 33
3.2.1 WiWg neaMon 33
3.2.2 Gnöna/d Reaktionen 34
Inhaltsverzeichnis
3.2.3 Aminierungen des Halogenalkyl Derivates 33 36
3.2.4 CaccW Kupplung 41
3.3. Aminoalkylether Derivate 44
3.3.1 WW/amso/vEthersynthese 44
3.4 Aminoalkylamino Derivate 46
3.4.1 Reduktive Aminierungen 46
3.4.1.1 Analytik der Verbindungen 58 und 59 50
3.5 Aminoalkylamid Derivate 54
3.5.1 Umesterung 55
3.5.2 Gerüstumlagerung 57
3.5.3 O Alkylierung unter Rhodium(ll) Katalyse 58
3.6 a Aminoketone 65
3.6.1 a Derivatisierung von Windaus Keton 66
3.6.2 Aminierungen des a Bromketons 69
3.7 Aminoalkohol Derivate 73
3.8 Tricyclische Derivate: Annellierung eines B Ring Äquivalents 74
3.8.1 Die SWfe Kupplung 74
3.8.2 D/e/s /l/cte/ Cycloadditionen 76
3.8.3 Weitere B Ring Synthesen 83
3.8.3.1 Annellierung fünfgliedriger Heterocyclen 84
4. Biologische Prüfung 89
4.1 Agar Diffusionstest 89
4.1.1 Testergebnisse 89
4.2 Test auf Inhibition der Ergosterolbiosynthese 97
4.3 Test auf Inhibition der Oxidosqualencyclasen 97
4.4 Allgemeine Struktur Aktivitäts Beziehungen 104
4.4.1 Inhibition der fungalen OSC 105
4.4.2 Inhibition der protozoischen OSC 106
4.4.4 Inhibition der herbaten OSC 107
4.4.5 Inhibition der humanen OSC 107
4.5MTT Test 108
5. Zusammenfassung 111
6. Experimenteller Teil 122
6.1 Geräte und Parameter 122
Inhaltsverzeichnis
6.2 Beschreibung der Substanzen 124
(1 fl,3afl,7afl) 4 Cyclopropyl 1 [(fl) 1,5 dimethylhexyl] 7a methyl octahydro
inden 4 ol (32) 124
(1 fl,7afl) 4 (3 Brompropyl) 2,3,5,6,7,7a hexahydro 7a methyl 1 [(fl) 1,5
dimethylhexyl] 1 H inden (33) 126
A/ Allyl A/ Methyl {3 [(1 fl,7afi) 1 [(fl) 1,5 dimethylhexyl] 7a methyl
2,3,5,6,7,7a hexahydro 1H inden 4 yl] propyl} amin (35) 128
N Methyl {3 [(1 fl,7afl) 1 [(fl) 1,5 dimethylhexyl] 7a methyl 2,3,5,6,7,7a
hexahydro 1H inden 4 yl] propyl} amin (36) 130
A/,/V Dimethyl {3 [(1 R,7afl) 1 [(fl) 1,5 dimethylhexyl] 7a methyl 2,3,5,6,7,7a
hexahydro 1H inden 4 yl] propyl} methylamin (37) 132
1 {3 [(1 fl,7afi) 1 [(H) 1 .S Dimethylhexyll^a methyl a.S.ö.ejJa hexahydro
1 W inden 4 yl] propyl} piperidin (38) 134
4 {3 [(1 fl,7afl) 1 [(fl) 1,5 Dimethylhexyl] 7a methyl 2,3,5,6,7,7a hexahydro
/W inden 4 yl] propyl} morpholin(39) 136
1 {3 [(1 R,7afl) 1 [(fl) 1,5 Dimethylhexyl] 7a methyl 2,3,5,6,7,7a hexahydro
1H inden 4 yl] propyl} pyridiniumbromid (40) 138
N,A/ Dimethyl {3 [(1 fl,7afl) 1 [(fl) 1,5 dimethylhexyl] 7a methyl 2,3,5,6,7,7a
hexahydro 1H inden 4 yl] propyl} amin A/ oxid(41) 140
(1 R,3aflS,4flS,7afl) 4 (3 Brompropyl) octahydro 7a methyl 1 [(R) 1,5
dimethylhexyl] 1 H inden (42a/b) 142
A^AIIyl {3 [(1 R,3aflS,4flS,7afl) 1 [(fl) 1,5 dimethylhexyl] 7a methyl
octahydro 1 W inden 4 yl] propyl} methylamin (43a/b) 144
(Isomeren Gemisch) 144
Trifluormethansulfonsäure {(1R,3afl,7afl) 1 [(fl) 1,5 dimethylhexyl] 7a methyl
2,3,3a,6,7,7a hexahydro 1H inden 4 yl} ester(44) 146
2 {(1 fl,3afl,7aR) 1 [(fl) 1,5 Dimethylhexyl] 7a methyl 2,3,3a,6,7,7a
hexahydro 1 H inden 4 ylethinyl} pyridin (45) 148
(1 fl,3afl,4S,7afl) 1 [(fl) 1,5 Dimethylhexyl] 7a methyl octahydro inden 4 ol
(47) 150
2 [(1 fl,3a/?,4S,7afl) 1 [(fl) 1,5 Dimethylhexyl] 7a methyl octahydro inden 4
yloxymethyl] pyridin (48) 152
2 [(1 fl,3afl,4S,7afl) 1 [(fl) 1,5 Dimethylhexyl] 7a methyl octahydro inden 4 yl
oxymethyn 1 methyl pyridiniumioclid(49) 154
Inhaltsverzeichnis
/V {(1 ft,3aflS,4RS,7afl) 1 [(fi) 1,5 Dimethylhexyl] 7a methyl octahydro inden
4 yl} A/,/Vkümethyl ethan 1,2 diamin(50) 156
A/ Methyl {(1 fl,3aft,4S,7afl) 1 [(fl) 1,5 Dimethylhexyl] 7a methyl octahydro
inden 4 yl} amin (51) 158
{(1 R,3afi,4S,7afi) 1 [(fl) 1,5 Dimethylhexyl] 7a methyl octahydro inden 4 yl}
(2 piperidin 1 yl ethyl) amin (53) 160
{(1 f?,3afl,4S,7afl) 1 [(fl) 1,5 Dimethylhexyl] 7a methyl octahydro inden 4 yl}
(2 pyrrolidin 1 yl ethyl) amin (54) 162
{(1 fl,3afl,4S,7afl) 1 [(fl) 1,5 Dimethylhexyl] 7a methyl octahydro inden 4 yl}
(2 morpholin 4 yl ethyl) amin(55) 164
{(1 fl,3afl,4S,7afl) 1 [(R) 1,5 Dimethylhexyl] 7a methyl octahydro inden 4 yl}
1 (1W imidazol 1 yl propyl) amin (56) 166
{(1 fl,3afl,4S,7afl) 1 [(fl) 1,5 Dimethylhexyl] 7a methyl octahydro inden 4 yl}
pyridin 2 ylmethylamin (57) 168
N {(1 fl,3afl,4S,7aR) 1 [(fl) 1,5 Dimethylhexyl] 7a methyl octahydro inden 4
yl]} A^methyl (pyridin 2 ylmethyl) amin (58) 170
A/ {(1 ff,3aS,4S,7afl) 1 [(R) 1,5 Dimethylhexyl] 7a methyl octahydro inden 4
yl]} W methyl (pyridin 2 ylmethyl) amin(59) 172
A/ (2 Dimethylamino ethyl) 2 [(1 fl,3afl,4S,7afl) 1 (1,5 dimethylhexyl) 7a
methyl octahydro inden 4 yloxy] W methyl acetamid (61) 174
Bromessigsäure[(1 R,3aR,4S,7aR) 1 (1,5 dimethylhexyl) 7a methyl octahydro
inden 4 yl] ester (62) 176
2 [A/ ( Dimethylaminoethyl) W methyl amino] essigsäure[(1R,3a/:?,4S,7afi) 1
(1,5 dimethyl hexyl) 7a methyl octahydro inden 4 yl] ester (63) 178
(3aS) 1 [(R,S) 1,5 Dimethylhexyl] 3a methyl 2,3,3a,4,5,6,7 hexahydro 2H
inden(64a/b) 180
{(1 R,3afl,4S,7afl) 1 [(fl)1,5 Dimethylhexyl] 7a methyl octahydro inden 4
yloxyj essigsäureethylester (65) 182
[(1 fl,3aft,4S,7afl) 1 (1,5 Dimethylhexyl) 7a methyl octahydro inden 4 yloxy]
essigsäure (66) 184
2 {(1 fl,3afl,4S,7a/?) 1 [(fl) 1,5 Dimethylhexyl] 7a methyl octahydro inden 4
yloxy] 1 (4 methyl piperazin 1 yl) ethanon (67) 186
{(1 fl,3afi,4S,7afl) 1 [(fl) 1,5 Dimethylhexyl] 7a methyl octahydro inden 4
yloxy} 1 (4 methyl [1,4]diazepan 1 yl) ethanon(68) 188
Inhaltsverzeichnis
(1 fl,7afl) 3a Brom 7a methyl 1 [(fl) 1,5 dimethylhexyl] octahydro inden 4 on
(69) 190
(1 ft,3afi,5f?,7afl) 5 Brom 7a methyl 1 [(fl) 1,5 dimethylhexyl] octahydro
inden 4 on (70) 191
{(1 R,3aR,7aR) 1 [(fl) 1,5 Dimethylhexyl] 7a methyl 2,3,3a,6,7,7a hexahydro
1W inden 4 yloxy} trimethylsilan(71) 193
(1 fl,3afiS,5flS,7afl) 5 (/V Allyl A/ methyl amino) 1 [(fl) 1,5 dimethylhexyl] 7a
methyl octahydro inden 4 on (72) 195
(1 R,3aRS,5RS,7aR) 5 N, A/ Dimethylamino 1 [(fl) 1,5 dimethylhexyl] 7a
methyl octahydro inden 4 on (73) 197
(1 fl,3aflS,5flS,7afl) 1 [(fl) 1,5 Dimethylhexyl] 7a methyl 5 (4 methyl
piperazin 1 yl) octahydro inden 4 on (74) 199
(1 fl,3aflS,5flS,7afl) 1 [(R) 1,5 Dimethylhexyl] 7a methyl 5 (piperidin 1 yl)
octahydro inden 4 on (75) 201
(1 fl,3aflS,5RS,7afl) 1 [(fl) 1,5 Dimethylhexyl] 5 (2,6 dimethylmorpholin 4 yl)
7a methyl octahydro inden 4 on (76) 203
(1 R,3aflS,5RS,7afl) 1 [(R) 1,5 Dimethylhexyl] 5 (4 hydroxy piperidin 1 yl) 7a
methyl octahydro inden 4 on (77) 205
(1 R,7aR)A [(H) 1,5 Dimethylhexyl] 7a methyl 4 methylamino 1,2,3,6,7,7a
hexahydro inden 5 on (80) 207
(1 ft,3aflS,4flS,5flS,7afl) 5 Dimethylamino 1 [(R) 1,5 dimethylhexyl] 7a
methyl octahydro inden 4 ol (81) 209
(1 fl,3aflS,5f?S,7afl) 1 [(fl) 1,5 Dimethylhexyl] 7a methyl 5 (4 methyl
piperazin 1 yl) octahydro inden 4 ol(82) 211
(1 fl,3afl,7afl) 2,3,3a,6,7,7a Hexahydro 7a methyl 1 [(fl) 1,5 dimethyl hexyl)
4 vinyl 1 H inden (83) 213
(4aflS,6afi,7fi,9af?) 7 [(R) 1,5 Dimethylhexyl] 6a methyl 2,5,6,6a,7,8,9,9a
octahydro 4aH cyclopenta[/]cinnolin 3,4 dicarbonsäurediethylester 215
(84) 215
(4aflS,6aR,7f?,9afl) 7 [(fl) 1,5 Dimethylhexyl] 6a methyl 2,5,6,6a,7,8,9,9a
octahydro 4a/+cyclopenta[qcinnolin 3,4 dicarbonsäurediisopropylester (85)
217
(4a/?,6afl,7fl,9afl) 7 [(fl) 1,5 Dimethylhexyl] 3,4,6a trimethyl
2,4,4a,5,6,6a,7,8,9,9a decahydro 3H ^ck penlal/|cinnolin(86) 219
Inhaltsverzeichnis
(4aS,6afl,7R,9afl) 7 [(fl) 1,5 Dimethylhexyl] 3,4,6a trimethyl
2,4,4a,5,6,6a,7,8,9,9a decahydro 3« cyclopenta[f]cinnolin (87) 219
(5S,8S,9fl,10S,14fl) 17 [(fl) 1,5 Dimethylhexyl] 14 methyl
2,3,4,5,6,7,8,9,10,11,12,14,15,16 tetradecahydro cyclopenta[a]phenantren 1
on(89) 222
{(3R,3aR,9bfl) 3 [(fl) 1,5 Dimethylhexyl] 3a methyl 2,3,3a,4,5,9b hexahydro
1 H 7,9 diaza cyclopenta[a]naphthalen 8 yl} amin (90) 224
{(3f?,3afl,9bR) 3 [(fl) 1,5 Dimethylhexyl] 3a methyl 2,3,3a,4,5,9b hexahydro
1H 7,9 diaza cyclopenta[a]naphtalen 8 yl} methylamin(91) 226
(1 fi,7afl) 1 [(fl) 1,5 Dimethylhexyl] 4 hydroxy 7a methyl 1,2,3,6,7,7a
hexahydro inden 5 on (92) 228
(5afi,6fl,8aflS) 6 [(fl) 1,5 Dimethylhexyl] 5a methyl 5,5a,6,7,8,8a hexahydro
4H 1 aza 3 thia as indacen 2 ylamin (93a/b) 230
A/ {(5afl,6R,8afi) 6 [(fi) 1,5 Dimethylhexyl] 5a methyl 5,5a,6,7,8,8a
hexahydro 4/+1 aza 3 thia as indacen 2 yl} guanidin (94) 232
6.3 Testmethoden der biologischen Prüfung 234
6.3.1 Agardiffusionstest 234
6.3.2 Ergosterol Biosynthese Inhibitoren 235
6.3.3 OSC Aktivität und Inhibition 235
6.3.3.1 Stämme von S. cerevisiae und Kulturbedingungen 236
6.3.3.2 Enzym Assay 236
6.3.4 MTT Test 238
7. Verzeichnis der Abkürzungen 239
8. Literaturverzeichnis 242 |
| any_adam_object | 1 |
| any_adam_object_boolean | 1 |
| author | Lange, Stefanie |
| author_facet | Lange, Stefanie |
| author_role | aut |
| author_sort | Lange, Stefanie |
| author_variant | s l sl |
| building | Verbundindex |
| bvnumber | BV021748933 |
| ctrlnum | (OCoLC)162456709 (DE-599)BVBBV021748933 |
| dewey-full | 615.19 |
| dewey-hundreds | 600 - Technology (Applied sciences) |
| dewey-ones | 615 - Pharmacology and therapeutics |
| dewey-raw | 615.19 |
| dewey-search | 615.19 |
| dewey-sort | 3615.19 |
| dewey-tens | 610 - Medicine and health |
| discipline | Medizin |
| discipline_str_mv | Medizin |
| edition | 1. Aufl. |
| format | Book |
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| genre | (DE-588)4113937-9 Hochschulschrift gnd-content |
| genre_facet | Hochschulschrift |
| id | DE-604.BV021748933 |
| illustrated | Illustrated |
| index_date | 2024-07-02T15:31:38Z |
| indexdate | 2024-07-09T20:43:09Z |
| institution | BVB |
| isbn | 9783899633856 3899633857 |
| language | German |
| oai_aleph_id | oai:aleph.bib-bvb.de:BVB01-014962170 |
| oclc_num | 162456709 |
| open_access_boolean | |
| owner | DE-19 DE-BY-UBM DE-12 |
| owner_facet | DE-19 DE-BY-UBM DE-12 |
| physical | 245 S. Ill., graph. Darst. 210 mm x 148 mm, 343 gr. |
| publishDate | 2006 |
| publishDateSearch | 2006 |
| publishDateSort | 2006 |
| publisher | Verl. Dr. Hut |
| record_format | marc |
| series2 | Pharmazeutische Chemie |
| spelling | Lange, Stefanie Verfasser aut Neuartige (S)-2,3-Oxidosqualencyclase-Inhibitoren Stefanie Lange 1. Aufl. München Verl. Dr. Hut 2006 245 S. Ill., graph. Darst. 210 mm x 148 mm, 343 gr. txt rdacontent n rdamedia nc rdacarrier Pharmazeutische Chemie Zugl.: München, Univ., Diss., 2006 Squalen (DE-588)4182616-4 gnd rswk-swf Enzyminhibitor (DE-588)4152479-2 gnd rswk-swf Cyclasen (DE-588)4468848-9 gnd rswk-swf (DE-588)4113937-9 Hochschulschrift gnd-content Squalen (DE-588)4182616-4 s Cyclasen (DE-588)4468848-9 s Enzyminhibitor (DE-588)4152479-2 s DE-604 HBZ Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=014962170&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Lange, Stefanie Neuartige (S)-2,3-Oxidosqualencyclase-Inhibitoren Squalen (DE-588)4182616-4 gnd Enzyminhibitor (DE-588)4152479-2 gnd Cyclasen (DE-588)4468848-9 gnd |
| subject_GND | (DE-588)4182616-4 (DE-588)4152479-2 (DE-588)4468848-9 (DE-588)4113937-9 |
| title | Neuartige (S)-2,3-Oxidosqualencyclase-Inhibitoren |
| title_auth | Neuartige (S)-2,3-Oxidosqualencyclase-Inhibitoren |
| title_exact_search | Neuartige (S)-2,3-Oxidosqualencyclase-Inhibitoren |
| title_exact_search_txtP | Neuartige (S)-2,3-Oxidosqualencyclase-Inhibitoren |
| title_full | Neuartige (S)-2,3-Oxidosqualencyclase-Inhibitoren Stefanie Lange |
| title_fullStr | Neuartige (S)-2,3-Oxidosqualencyclase-Inhibitoren Stefanie Lange |
| title_full_unstemmed | Neuartige (S)-2,3-Oxidosqualencyclase-Inhibitoren Stefanie Lange |
| title_short | Neuartige (S)-2,3-Oxidosqualencyclase-Inhibitoren |
| title_sort | neuartige s 2 3 oxidosqualencyclase inhibitoren |
| topic | Squalen (DE-588)4182616-4 gnd Enzyminhibitor (DE-588)4152479-2 gnd Cyclasen (DE-588)4468848-9 gnd |
| topic_facet | Squalen Enzyminhibitor Cyclasen Hochschulschrift |
| url | http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=014962170&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
| work_keys_str_mv | AT langestefanie neuartiges23oxidosqualencyclaseinhibitoren |