Strukturanaloga von Annonaceen-Acetogeninen und von (+/-)-4-Ipomeanol:
Gespeichert in:
| 1. Verfasser: | |
|---|---|
| Format: | Buch |
| Sprache: | German |
| Veröffentlicht: |
München
Hut
2007
|
| Ausgabe: | 1. Aufl. |
| Schriftenreihe: | Pharmazeutische Chemie
|
| Schlagworte: | |
| Online-Zugang: | Inhaltsverzeichnis |
| Beschreibung: | Zugl.: München, Univ., Diss., 2007. - Literaturverz. S. 180 - 182 |
| Beschreibung: | XIII, 184 S. graph. Darst. 210 mm x 148 mm, 263 gr. |
| ISBN: | 9783899635706 3899635701 |
Internformat
MARC
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|---|---|---|---|
| 001 | BV022861375 | ||
| 003 | DE-604 | ||
| 005 | 20071204 | ||
| 007 | t | ||
| 008 | 071001s2007 d||| m||| 00||| ger d | ||
| 016 | 7 | |a 985380608 |2 DE-101 | |
| 020 | |a 9783899635706 |c Pb. : EUR 39.00 |9 978-3-89963-570-6 | ||
| 020 | |a 3899635701 |c Pb. : EUR 39.00 |9 3-89963-570-1 | ||
| 024 | 3 | |a 9783899635706 | |
| 035 | |a (OCoLC)219153721 | ||
| 035 | |a (DE-599)DNB985380608 | ||
| 040 | |a DE-604 |b ger |e rakddb | ||
| 041 | 0 | |a ger | |
| 049 | |a DE-12 |a DE-29T |a DE-19 | ||
| 100 | 1 | |a Unterreitmeier, Doris |d 1975- |e Verfasser |0 (DE-588)123570492 |4 aut | |
| 245 | 1 | 0 | |a Strukturanaloga von Annonaceen-Acetogeninen und von (+/-)-4-Ipomeanol |c von Doris Unterreitmeier |
| 250 | |a 1. Aufl. | ||
| 264 | 1 | |a München |b Hut |c 2007 | |
| 300 | |a XIII, 184 S. |b graph. Darst. |c 210 mm x 148 mm, 263 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., 2007. - Literaturverz. S. 180 - 182 | ||
| 655 | 7 | |0 (DE-588)4113937-9 |a Hochschulschrift |2 gnd-content | |
| 856 | 4 | 2 | |m DNB Datenaustausch |q application/pdf |u http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=016066597&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |3 Inhaltsverzeichnis |
| 999 | |a oai:aleph.bib-bvb.de:BVB01-016066597 | ||
Datensatz im Suchindex
| _version_ | 1804137115333689344 |
|---|---|
| adam_text | INHALTSVERZEICHNIS
1
FORMELVERZEICHNIS
..............................................................................................................................
1
1.1
NEUE
MONOSUBSTITUIERTE
FURAN
U.
THIOPHEN-DERIVATE
..........................................................
1
1.2
KETON-DERIVATE
............................................................................................................................
3
13
THF-DERIVATE
..............................................................................................................................
3
1.4
AUFBAU
DES
CI-C
X
FRAGMENTES
..................................................................................................
4
1.5
2,5-DISUBSTITUIERTE
FURANE
........................................................................................................
5
1.6
ALTERNATIVE
WEGE
.........................................................................................................................6
1.7
IPOMEANOL-ANALOGA
.....................................................................................................................
7
2
EINLEITUNG.
...........................................................................................................................................
8
2.1
ANNONACEAE
...................................................................................................................................
9
2.1.1
UEBERSICHT
UND
INHALTSSTOFFE
................................................................................................................
9
2.1.1.1
ACETOGENINE
AUS
ANNONACEAE
.................................................................................................
10
2.1.1.2
B
IOSYNTHESE
DER
ACETOGENINE
..................................................................................................
11
2.1.2
BIOLOGISCHE
AKTIVITAET
.......................................................................................................................
14
2.2
()-4-IPOMEANOL
........................................................................................................................
16
2.2.1
URSPRUNG
UND
UEBERSICHT
....................................................................................................................
16
2.2.2
BIOSYNTHESE
VON
()-4-IPOMEANOL
...................................................................................................
16
2.2.3
TOTALSYNTHESEN
...................................................................................................................................
19
2.2.4 BIOLOGISCHE
AKTIVITAET
.......................................................................................................................
21
3
THEMENSTELLUNG
UND
SYNTHESEPLANUNG
...................................................................................
22
3.1
THEMENSTELLUNG
..................................................................................................................22
3.2
SYNTHESEPLANUNG
......................................
22
3.2.1
ANNONACEEN-ACETOGENINE
...............................................................................................................
22
3.2.2
()-4-IPOMEANOL-ANALOGA
...............................................................................................................
25
4
SYNTHESEN
..........................................................................................................................................
27
4.1
SYNTHESE
VON
ANALOGA
DER
ANNONACEEN-ACETOGENINE
........................................................
27
4.1.1
EINFACH
SUBSTITUIERTE
FURAN
UND
THIOPHENDERIVATE
.......................................................................
27
4.1.1.1
GRIGNARD-REAKTION
..................................................................................................................
27
4.1.1.2
FRIEDEL-CRAFTS-ACYLIERUNG
.......................................................................................................
30
4.1.1.3
SOLVOLYSE
.................................................................................................................................
31
4.1.1.4
SCHUTZGRUPPEN
........................................................................................................................
33
4.1.1.5
HYDRIERUNG
..............................................................................................................................
34
4.1.1.6
VERESTERUNG
.............................................................................................................................
35
4.1.1.7
SHARPLESS-DIHYDROXYLIERUNG
...................................................................................................
38
4.1.1.8
RING
CLOSING
METATHESIS
..........................................................................................................
42
4.1.1.9
OEFFNUNG
DER
LACTONE
...............................................................................................................
46
4.1.1.10
SONOGASHIRA-REAKTION
.............................................................................................................
47
4.1.1.11
HYDRATISIERUNG
DER
DREIFACHBINDUNG
.......................................................................................
51
4.1.2
2,5-DISUBSTITUIERTE
FURANE
...............................................................................................................
52
4.1.2.1
LITHIIERUNG/
ALKYLIERUNG
.........................................................................................................
52
4.1.2.2
GRIGNARD-REAKTION
..................................................................................................................
54
4.1.2.3
KETTEN
VERLAENGERUNG
DER
1,5-DISUBSTITUIERTEN
FURANE
DURCH
RCM
...........................................
55
4.2
SYNTHESE
VON
()-4-IPOMEANOL UND
DERIVATEN
....................................................................
56
4.2.1
GRIGNARD-REAKTION
...........................................................................................................................
56
4.2.2 OXIDATION
NACH
DESS-MARTIN
...........................................................................................................
58
4.2.3
()-4-IPOMEANOL
..............................................................................................................................
60
4.2.4 DARSTELLUNG
DES
2-FURYL-ISOMERS
.....................................................................................................
61
4.2.5
DERIVATISIERUNG
VON
IPOMEANOL-ANALOGA
DURCH
HYDROXYLIERUNG
ODER
VERESTERUNG
......................
62
4.2.6
THIO-IPOMEANOL
...............................................................................................................................
63
XI
5
BIOLOGISCHE
TESTUNG
.........................................................................................
64
5.1
EINFUEHRUNG
................................................................................................................................
64
5.2
METHODEN
UND
ERGEBNISSE
.......................................................................................................
64
5.2.1
TESTUNG
AUF
ANTIBIOTISCHE
UND
ANTIMYKOTISCHE
AKTIVITAET
................................................................
64
5.2.1.1
AGARDIFFUSIONSTEST
....................................................................................................................
64
5.2.1.2
TESTUNG
AUF
ZYTOTOXISCHE
AKTIVITAET
..........................................................................................
65
5.2.1.3
ZYTOTOXIZITAETSTEST
DER
KINDERONKOLOGIE
UND
-HAEMATOLOGIE
DER
HEINRICH
HEINE
UNIVERSITAET
DUESSELDORF
...............................................................................................................................
74
5.2.1.4
TESTUNGEN
DES
NATIONAL
CANCER
INSTITUTE
.................................................................................
76
5.3
ZUSAMMENFASSUNG
....................................................................................................................
78
5.3.1
ANALOGA
VON
ANNONACEEN-ACETOGENIN
............................................................................................
78
5.3.2
IPOMEANOL
UND
ANALOGA
...................................................................................................................
83
5.3.3
BIOLOGISCHE
PRUEFUNG
.........................................................................................................................
84
6
EXPETIMENTELLER
TEIL
......................................................................................................................
86
6.1
ALLGEMEINE
ANGABEN
................................................................................................................
86
6.2
ALLGEMEINE
ARBEITS
VORSCHRIFTEN
.............................................................................................
87
6.2.1
AAV_1
(DARSTELLUNG
VON
GRIGNARD-REAGENZIEN)
............................................................................
87
6.2.2
AAV_2
(GRIGNARD-REAKTION)
..........................................................................................................
87
63
SYNTHESEN
...................................................................................................................................
88
6.3.1
MONOSUBSTITUIERTE
FURAN
UND
THIOPHEN-DERIVATE
..........................................................................
88
6.3.1.1
L-(FURAN-2-YL)-TRIDECAN-L-OL
(UK_1.1)
....................................................................................
88
6.3.1.2
L-(FURAN-3-YL)-TRIDECAN-L-OL
(UK_1.2)
....................................................................................
89
6.3.1.3
2-[L-(TERT.-BUTYLDIMETHYLSILYLOXY)-TRIDECYL]-FURAN
(UK_1.3)
.................................................
90
6.3.1.4
2-(L-BENZYLOXY-TRIDECYL)-FURAN
(UK_1.4)
..............................................................................
91
6.3.1.5
[L-(FURAN-2-YL)-TRIDECYL]-UNDEC-10-ENOAT
(UK_1.5)
...............................................................
92
6.3.1.6
L-(FURAN-2-YL)-PROP-2-EN-L-OL
(UK_1.6)
.................................................................................
93
6.3.1.7
L-(FURAN-2-YL)-BUT-3-EN-L-OL
(UK_1.7)
....................................................................................
94
6.3.1.8
L-(FURAN-2-YL)-PENT-4-EN-L-OL
(UK_1.8)
..................................................................................
95
6.3.1.9
L-(FURAN-2-YL)-HEX-5-EN-L-OL
(UK_1.9)
...................................................................................
96
6.3.1.10
[L-(FURAN-2-YL)-HEX-5-ENYL]-OCTANOAT
(UK_1.10)
...................................................................
97
6.3.1.11
[L-(FURAN-2-YL)-5,6-DIHYDROXYHEXYL)-OCTANOAT
(UK_1.1
1)
.....................................................
98
6.3.1.12
[L-(FURAN-2-YL)-5,6-BIS-(OCTANOYLOXY)-HEXYL]-OCTANOAT
(UK_1.12)
........................................
99
6.3.1.13
6-(FURAN-2-YL)-HEXAN-L,2,6-TRIOL
(UK_1.13)
..........................................................................
101
6.3.1.14
2-(L-BENZYLOXYHEX-5-EN-L-YL)-FURAN
(UK_1.14)
...................................................................
102
6.3.1.15
6-BENZYLOXY-6-(FURAN-2-YL)-HEXAN-1,2-DIOL
(UK_1.15)
........................................................
103
6.3.1.16
2-[L,5,6-TRIS(BENZYLOXY)-HEX-L-YL]-FURAN
(UK_1.16)
............................................................
104
6.3.1.17
2-[L-(TERT.-BUTYLDIMETHYLSILYLOXY)-HEX-5-EN-L-YL]-FURAN
(UK_1.17)
....................................
106
6.3.1.18
L-(THIOPHEN-2-YL)-TRIDECAN-L-OL
(UK_1.18)
..........................................................................
107
6.3.1.19
L-(THIOPHEN-3-YL)-TRIDECAN-L-OL
(UK_1.19)
..........................................................................
108
6.3.1.20
L-(THIOPHEN-2-YL)-PROP-2-EN-L-OL
(UK_1.20)
.......................................................................
109
6.3.1.21
L-(THIOPHEN-2-YL)-BUT-3-EN-L-OL
(UK_1.21)
.........................................................................
110
6.3.1.22
L-(THIOPHEN-3-YL)-PENT-4-EN-L-OL
(UK_1.22)
.......................................................................
112
6.3.2
KETON-DERIVATE
...............................................................................................................................
113
6.3.2.1
L-(FURAN-2-YL)-DECAN-L-ON
(UK_2.1)
.....................................................................................
113
6.3.2.2
L-(FURAN-2-YL)-TRIDECAN-L-ON
(UK_2.2)
................................................................................
114
6.3.2.3
TRIFIUORESSIGSAEURE-[10-(FURAN-2-YL)-L-METHYL-10-OXO]-DECYLESTER
(UK_2.3)
......................
115
6.3.2.4
TRIFLUORESSIGSAEURE-[L-ETHYL-9-(FURAN-2-YL)-9-OXO]-NONYLESTER
(UK_2.4)
..............................
116
6.3.2.5
L-(FURAN-2-YL)-10-HYDROXYUNDECAN-L-ON
(UK_2.5)
............................................................
117
6.3.2.6
L-(FURAN-2-YL)-9-HYDROXYUNDECAN-L-ON
(UK_2.6)
................................................................
118
6.3.3
TETRAHYDROFURAN-DERIVATE
...............................................................................................................
119
6.3.3.1
L-(TETRAHYDROFURAN-2-YL)-TRIDECAN-L-OL
(UK_3.1)
...............................................................
119
6.3.3.2
L-[5-(L-HYDROXYPENTYL)-TETRAHYDROFURAN-2-YL]-TRIDECAN-L-OL
(UK_3.2)
................................
120
6.3.3.3
L-[5-(L-HYDROXYHEXYL)-TETRAHYDROFURAN-2-YL]-TRIDECAN-L-OL
(UK_3.3)
.................................
121
6.3.4
AUFBAU
DES
C-CX
FRAGMENTES
........................................................................................................
122
6.3.4.1
UNDEC-10-ENSAEURE-[L-(FURAN-2-YL)-BUT-3-EN-L-YL]-ESTER
(UK_4.1)
........................................
122
6.3.4.2
UNDEC-10-ENSAEURE-[L-(FURAN-2-YL)-PENT-4-EN-L-YL]-ESTER
(UK_4.2)
......................................
124
6.3.4.3
UNDEC-10-ENSAEURE-[L-(FURAN-2-YL)-HEX-5-EN-L-YL]-ESTER
(UK_4.3)
.......................................
125
XII
6.3.5
MACROLACTONE
...................................................................................................................................
126
6.3.5.1
14-(FURAN-2-YL)-OXACYCLOTETRADEC-LL-EN-2-ON
(UK_4.4)
.......................................................
126
6.3.5.2
15-(FURAN-2-YL)-L-OXACYCLOPENTADEC-LL-EN-2-ON
(UK_4.5)
..................................................
127
6.3.5.3
16-(FURAN-2-YL)-L-OXACYCLOHEXADEC-L
L-EN-2-ON
(UK_4.6)
...................................................
128
6.3.5.4
(E/Z)-14-(FURAN-2-YL)-14-HYDROXY-TETRADEC-10-ENSAEURE
(UK_4.7)
.......................................
129
6.3.5.5
(E/Z)-17-FURAN-2-YL-17-HYDROXY-2,2-DIMETHYLHEPTADEC-12-EN-3-ON
(UK_4.8)
..................
130
6.3.6
2,5-DISUBSTITUIERTE
FURANE
..............................................................................................................
131
6.3.6.1
L-[5-(L-HYDROXY-PENT-4-ENYL)-FURAN-2-YL]-TRIDECAN-L-OL
(UK_5.1)
.......................................
131
6.3.6.2
L-[5-(L-HYDROXY-HEX-5-ENYL)-FURAN-2-YL]-TRIDECAN-L-OL
(UK_5.2)
........................................
133
6.3.6.3
1-[5-(1-TERT-BUTYLDIMETHYLSILYLOXY-HEX-5-ENYL)-FURAN-2-YL]-TRIDECAN-1-OL
(UK_5.3)
..........
135
OE.3.6.4
L-(5-UNDECYL-FURAN-2-YL)-PENT-4-EN-L-OL
(UK_5.4)
...............................................................
137
6.3.6.5
1-[5-(PENT-4-ENYL)-FURAN-2-YL]-TRIDECAN-1-OL
(UK_5.5)
.........................................................
138
6.3.6.6
L-{5-[L-(TERT-BUTYLDIMETHYLSILYLOXY)-TRIDECYL]-FURAN-2-YL}-PENT-4-EN-L-OL
(UK_5.6)
.........
139
6.3.6.7
1
-TERT.
BUTYL
[5-(1
-TERT.
-BUTYLDIMETHYLSILYLOXYTRIDECYL)-FURAN-2-YL]-PENT-4-EN
(UK_5.7)..
141
6.3.6.8
UNDEC-10-ENSAEURE-(5-[1-(TERT.-BUTYLDIMETHYLSILYLOXY-TRIDECYL)-FURAN-2-YL]
PENT-4-EN-L-YL}-ESTER
(UK_5.8)
............................................................................................
143
6.3.6.9
15-{5-[1-(TERT-BUTYL-DIMETHYL-SILANYLOXY)-TRIDECYL]-FURAN-2-YL)-1-OXACYCLO
PENTADEC-LL-EN-2-ON
(UK_5.9)
.............................................................................................
145
6.3.7
ALTERNATIVE
SYNTHESEWEGE
..............................................................................................................
147
6.3.7.1
5-(LL-HYDROXYUNDEC-L-INYL)-FURAN-2-CARBALDEHYD
(UK_6.1)
...............................................
147
6.3.7.2
LL-(2-FORMYL-FURAN-5-YL)-UNDEC-10-INSAEURE
(UK_6.2)
..........................................................
148
6.3.7.3
UNDEC
1
0-INSAEUREMETHYLESTER
(UK_6.3)
................................................................................
149
6.3.7.4
1
L-(2-FORMYL-FURAN-5-YL)-UNDEC-LO-INSAEUREMETHYLESTER
(UK_6.4)
......................................
150
6.3.7.5
()-UNDEC-10-INSAEURE-[L-(ETHOXYCARBONYL)-ETHYL]-ESTER
(UK_6.5)
.......................................
151
6.3.7.6
1
L-(5-FORMYL-FURAN-2-YL)-UNDEC-10-INSAEURE-[L-(ETHOXYCCU-BONYL)-ETHYL]-ESTER
(UK_6.6)..
152
6.3.7.7
H-[5-(L-HYDROXYTRIDECYL)-FURAN-2-YL]-UNDEC-10-IN-L-OL
(UK_6.7)
.....................................
154
6.3.7.8
LL-[5-(L-HYDROXYTRIDECYL)-FURAN-2-YL]-UNDEC-10-INSAEUREMETHYLESTER
(UK_6.8)
.................
155
6.3.7.9
1
1-[5-(
L-HYDROXY-TRIDECYL)-FURAN-2-YL]-UNDEC-10-INSAEURE-L-ETHOXYCARBONYL
ETHYL
ESTER
(UK_6.9)
..............................................................................................................
157
6.3.7.10
LL-HYDROXY-L-[5-(L-HYDROXYTRIDECYL)-FURAN-2-YL]-UNDECAN-L-ON
(UK_6.10)
......................
158
6.3.8
IPOMEANOL-ANALOGA
........................................................................................................................
160
6.3.8.1
L-(FURAN-3-YL)-BUT-3-EN-L-OL
(UK_7.1)
..................................................................................
160
6.3.8.2
L-(FURAN-3-YL)-PENT-4-EN-L-OL
(UK_7.2)
................................................................................
161
6.3.8.3
L-(FURAN-3-YL)-PENT-4-EN-L-ON
(UK_7.3)
...............................................................................
162
6.3.8.4
TRIFLUORESSIGSAEURE-[4-(FURAN-3-YL)-L-METHYL-4-OXO]-BUTYLESTER
(UK_7.4)
............................
163
6.3.8.5
()-4-IPOMEANOL
(UK_7.5)
.....................................................................................................
164
6.3.8.6
TRIFLUORESSIGSAEURE-[4-(FURAN-2-YL)-L-METHYL-4-OXO]-BUTYLESTER
(UK_7.6)
............................
165
6.3.8.7
L-(FURAN-2-YL)-PENT-4-EN-L-ON
(UK_7.7)
...............................................................................
166
6.3.8.8
L-(FURAN-2-YL)-4-HYDROXY-PENTAN-L-ON
(UK_7.8)
..................................................................
167
6.3.8.9
L-(FURAN-3-YL)-HEX-5-EN-L-OL
(UK_7.9)
.................................................................................
168
6.3.8.10
OCTANSAEURE-[L-(FURAN-3-YL)-HEX-5-EN-L-YL]-ESTER
(UK_7.10)
................................................
169
6.3.8.11
OCTANSAEURE-[L-(FURAN-3-YL)-5,6-DIHYDROXY]-HEXYL-ESTER
(UK_7.1
1)
.....................................
170
6.3.8.12
6-(FURAN-3-YI)-HEXAN-L,2,6-TRIYLTRIOCTANOAT
(UK_7.12)
........................................................
171
6.3.8.13
5-(THIOPHEN-3-YL)-PENT-4-IN-2-OL
(UK_7.13)
.......................................................................
173
6.3.8.14
4-HYDROXY-L-(THIOPHEN-3-YL)-PENTAN-L-ON
(UK_7.14)
.........................................................
174
6.4
BIOLOGISCHE
PRUEFUNG
..............................................................................................................
175
6.4.1
AGARDIFFUSIONSTEST
..........................................................................................................................
175
6.4.1.1
TESTSUBSTANZEN
.......................................................................................................................
175
6.4.1.2
NAEHRMEDIEN
............................................................................................................................
175
6.4.1.3
VORGEHENS
WEISE
.....................................................................................................................
176
6.4.2
MTT-ASSAY
....................................................................................................................................
176
6.4.2.1
ZELLKULTUR
...............................................................................................................................
176
6.4.3
TESTUNG
AM
NATIONAL
CANCER
INSTITUTE
...........................................................................................
179
6.4.3.1
ZELLKULTUR
...............................................................................................................................
179
7
LITERATURVERZEICHNIS
....................................................................................................................
180
XIII
|
| adam_txt |
INHALTSVERZEICHNIS
1
FORMELVERZEICHNIS
.
1
1.1
NEUE
MONOSUBSTITUIERTE
FURAN
U.
THIOPHEN-DERIVATE
.
1
1.2
KETON-DERIVATE
.
3
13
THF-DERIVATE
.
3
1.4
AUFBAU
DES
CI-C
X
FRAGMENTES
.
4
1.5
2,5-DISUBSTITUIERTE
FURANE
.
5
1.6
ALTERNATIVE
WEGE
.6
1.7
IPOMEANOL-ANALOGA
.
7
2
EINLEITUNG.
.
8
2.1
ANNONACEAE
.
9
2.1.1
UEBERSICHT
UND
INHALTSSTOFFE
.
9
2.1.1.1
ACETOGENINE
AUS
ANNONACEAE
.
10
2.1.1.2
B
IOSYNTHESE
DER
ACETOGENINE
.
11
2.1.2
BIOLOGISCHE
AKTIVITAET
.
14
2.2
()-4-IPOMEANOL
.
16
2.2.1
URSPRUNG
UND
UEBERSICHT
.
16
2.2.2
BIOSYNTHESE
VON
()-4-IPOMEANOL
.
16
2.2.3
TOTALSYNTHESEN
.
19
2.2.4 BIOLOGISCHE
AKTIVITAET
.
21
3
THEMENSTELLUNG
UND
SYNTHESEPLANUNG
.
22
3.1
THEMENSTELLUNG
.22
3.2
SYNTHESEPLANUNG
.
22
3.2.1
ANNONACEEN-ACETOGENINE
.
22
3.2.2
()-4-IPOMEANOL-ANALOGA
.
25
4
SYNTHESEN
.
27
4.1
SYNTHESE
VON
ANALOGA
DER
ANNONACEEN-ACETOGENINE
.
27
4.1.1
EINFACH
SUBSTITUIERTE
FURAN
UND
THIOPHENDERIVATE
.
27
4.1.1.1
GRIGNARD-REAKTION
.
27
4.1.1.2
FRIEDEL-CRAFTS-ACYLIERUNG
.
30
4.1.1.3
SOLVOLYSE
.
31
4.1.1.4
SCHUTZGRUPPEN
.
33
4.1.1.5
HYDRIERUNG
.
34
4.1.1.6
VERESTERUNG
.
35
4.1.1.7
SHARPLESS-DIHYDROXYLIERUNG
.
38
4.1.1.8
RING
CLOSING
METATHESIS
.
42
4.1.1.9
OEFFNUNG
DER
LACTONE
.
46
4.1.1.10
SONOGASHIRA-REAKTION
.
47
4.1.1.11
HYDRATISIERUNG
DER
DREIFACHBINDUNG
.
51
4.1.2
2,5-DISUBSTITUIERTE
FURANE
.
52
4.1.2.1
LITHIIERUNG/
ALKYLIERUNG
.
52
4.1.2.2
GRIGNARD-REAKTION
.
54
4.1.2.3
KETTEN
VERLAENGERUNG
DER
1,5-DISUBSTITUIERTEN
FURANE
DURCH
RCM
.
55
4.2
SYNTHESE
VON
()-4-IPOMEANOL UND
DERIVATEN
.
56
4.2.1
GRIGNARD-REAKTION
.
56
4.2.2 OXIDATION
NACH
DESS-MARTIN
.
58
4.2.3
()-4-IPOMEANOL
.
60
4.2.4 DARSTELLUNG
DES
2-FURYL-ISOMERS
.
61
4.2.5
DERIVATISIERUNG
VON
IPOMEANOL-ANALOGA
DURCH
HYDROXYLIERUNG
ODER
VERESTERUNG
.
62
4.2.6
THIO-IPOMEANOL
.
63
XI
5
BIOLOGISCHE
TESTUNG
.
64
5.1
EINFUEHRUNG
.
64
5.2
METHODEN
UND
ERGEBNISSE
.
64
5.2.1
TESTUNG
AUF
ANTIBIOTISCHE
UND
ANTIMYKOTISCHE
AKTIVITAET
.
64
5.2.1.1
AGARDIFFUSIONSTEST
.
64
5.2.1.2
TESTUNG
AUF
ZYTOTOXISCHE
AKTIVITAET
.
65
5.2.1.3
ZYTOTOXIZITAETSTEST
DER
KINDERONKOLOGIE
UND
-HAEMATOLOGIE
DER
HEINRICH
HEINE
UNIVERSITAET
DUESSELDORF
.
74
5.2.1.4
TESTUNGEN
DES
NATIONAL
CANCER
INSTITUTE
.
76
5.3
ZUSAMMENFASSUNG
.
78
5.3.1
ANALOGA
VON
ANNONACEEN-ACETOGENIN
.
78
5.3.2
IPOMEANOL
UND
ANALOGA
.
83
5.3.3
BIOLOGISCHE
PRUEFUNG
.
84
6
EXPETIMENTELLER
TEIL
.
86
6.1
ALLGEMEINE
ANGABEN
.
86
6.2
ALLGEMEINE
ARBEITS
VORSCHRIFTEN
.
87
6.2.1
AAV_1
(DARSTELLUNG
VON
GRIGNARD-REAGENZIEN)
.
87
6.2.2
AAV_2
(GRIGNARD-REAKTION)
.
87
63
SYNTHESEN
.
88
6.3.1
MONOSUBSTITUIERTE
FURAN
UND
THIOPHEN-DERIVATE
.
88
6.3.1.1
L-(FURAN-2-YL)-TRIDECAN-L-OL
(UK_1.1)
.
88
6.3.1.2
L-(FURAN-3-YL)-TRIDECAN-L-OL
(UK_1.2)
.
89
6.3.1.3
2-[L-(TERT.-BUTYLDIMETHYLSILYLOXY)-TRIDECYL]-FURAN
(UK_1.3)
.
90
6.3.1.4
2-(L-BENZYLOXY-TRIDECYL)-FURAN
(UK_1.4)
.
91
6.3.1.5
[L-(FURAN-2-YL)-TRIDECYL]-UNDEC-10-ENOAT
(UK_1.5)
.
92
6.3.1.6
L-(FURAN-2-YL)-PROP-2-EN-L-OL
(UK_1.6)
.
93
6.3.1.7
L-(FURAN-2-YL)-BUT-3-EN-L-OL
(UK_1.7)
.
94
6.3.1.8
L-(FURAN-2-YL)-PENT-4-EN-L-OL
(UK_1.8)
.
95
6.3.1.9
L-(FURAN-2-YL)-HEX-5-EN-L-OL
(UK_1.9)
.
96
6.3.1.10
[L-(FURAN-2-YL)-HEX-5-ENYL]-OCTANOAT
(UK_1.10)
.
97
6.3.1.11
[L-(FURAN-2-YL)-5,6-DIHYDROXYHEXYL)-OCTANOAT
(UK_1.1
1)
.
98
6.3.1.12
[L-(FURAN-2-YL)-5,6-BIS-(OCTANOYLOXY)-HEXYL]-OCTANOAT
(UK_1.12)
.
99
6.3.1.13
6-(FURAN-2-YL)-HEXAN-L,2,6-TRIOL
(UK_1.13)
.
101
6.3.1.14
2-(L-BENZYLOXYHEX-5-EN-L-YL)-FURAN
(UK_1.14)
.
102
6.3.1.15
6-BENZYLOXY-6-(FURAN-2-YL)-HEXAN-1,2-DIOL
(UK_1.15)
.
103
6.3.1.16
2-[L,5,6-TRIS(BENZYLOXY)-HEX-L-YL]-FURAN
(UK_1.16)
.
104
6.3.1.17
2-[L-(TERT.-BUTYLDIMETHYLSILYLOXY)-HEX-5-EN-L-YL]-FURAN
(UK_1.17)
.
106
6.3.1.18
L-(THIOPHEN-2-YL)-TRIDECAN-L-OL
(UK_1.18)
.
107
6.3.1.19
L-(THIOPHEN-3-YL)-TRIDECAN-L-OL
(UK_1.19)
.
108
6.3.1.20
L-(THIOPHEN-2-YL)-PROP-2-EN-L-OL
(UK_1.20)
.
109
6.3.1.21
L-(THIOPHEN-2-YL)-BUT-3-EN-L-OL
(UK_1.21)
.
110
6.3.1.22
L-(THIOPHEN-3-YL)-PENT-4-EN-L-OL
(UK_1.22)
.
112
6.3.2
KETON-DERIVATE
.
113
6.3.2.1
L-(FURAN-2-YL)-DECAN-L-ON
(UK_2.1)
.
113
6.3.2.2
L-(FURAN-2-YL)-TRIDECAN-L-ON
(UK_2.2)
.
114
6.3.2.3
TRIFIUORESSIGSAEURE-[10-(FURAN-2-YL)-L-METHYL-10-OXO]-DECYLESTER
(UK_2.3)
.
115
6.3.2.4
TRIFLUORESSIGSAEURE-[L-ETHYL-9-(FURAN-2-YL)-9-OXO]-NONYLESTER
(UK_2.4)
.
116
6.3.2.5
L-(FURAN-2-YL)-10-HYDROXYUNDECAN-L-ON
(UK_2.5)
.
117
6.3.2.6
L-(FURAN-2-YL)-9-HYDROXYUNDECAN-L-ON
(UK_2.6)
.
118
6.3.3
TETRAHYDROFURAN-DERIVATE
.
119
6.3.3.1
L-(TETRAHYDROFURAN-2-YL)-TRIDECAN-L-OL
(UK_3.1)
.
119
6.3.3.2
L-[5-(L-HYDROXYPENTYL)-TETRAHYDROFURAN-2-YL]-TRIDECAN-L-OL
(UK_3.2)
.
120
6.3.3.3
L-[5-(L-HYDROXYHEXYL)-TETRAHYDROFURAN-2-YL]-TRIDECAN-L-OL
(UK_3.3)
.
121
6.3.4
AUFBAU
DES
C-CX
FRAGMENTES
.
122
6.3.4.1
UNDEC-10-ENSAEURE-[L-(FURAN-2-YL)-BUT-3-EN-L-YL]-ESTER
(UK_4.1)
.
122
6.3.4.2
UNDEC-10-ENSAEURE-[L-(FURAN-2-YL)-PENT-4-EN-L-YL]-ESTER
(UK_4.2)
.
124
6.3.4.3
UNDEC-10-ENSAEURE-[L-(FURAN-2-YL)-HEX-5-EN-L-YL]-ESTER
(UK_4.3)
.
125
XII
6.3.5
MACROLACTONE
.
126
6.3.5.1
14-(FURAN-2-YL)-OXACYCLOTETRADEC-LL-EN-2-ON
(UK_4.4)
.
126
6.3.5.2
15-(FURAN-2-YL)-L-OXACYCLOPENTADEC-LL-EN-2-ON
(UK_4.5)
.
127
6.3.5.3
16-(FURAN-2-YL)-L-OXACYCLOHEXADEC-L
L-EN-2-ON
(UK_4.6)
.
128
6.3.5.4
(E/Z)-14-(FURAN-2-YL)-14-HYDROXY-TETRADEC-10-ENSAEURE
(UK_4.7)
.
129
6.3.5.5
(E/Z)-17-FURAN-2-YL-17-HYDROXY-2,2-DIMETHYLHEPTADEC-12-EN-3-ON
(UK_4.8)
.
130
6.3.6
2,5-DISUBSTITUIERTE
FURANE
.
131
6.3.6.1
L-[5-(L-HYDROXY-PENT-4-ENYL)-FURAN-2-YL]-TRIDECAN-L-OL
(UK_5.1)
.
131
6.3.6.2
L-[5-(L-HYDROXY-HEX-5-ENYL)-FURAN-2-YL]-TRIDECAN-L-OL
(UK_5.2)
.
133
6.3.6.3
1-[5-(1-TERT-BUTYLDIMETHYLSILYLOXY-HEX-5-ENYL)-FURAN-2-YL]-TRIDECAN-1-OL
(UK_5.3)
.
135
OE.3.6.4
L-(5-UNDECYL-FURAN-2-YL)-PENT-4-EN-L-OL
(UK_5.4)
.
137
6.3.6.5
1-[5-(PENT-4-ENYL)-FURAN-2-YL]-TRIDECAN-1-OL
(UK_5.5)
.
138
6.3.6.6
L-{5-[L-(TERT-BUTYLDIMETHYLSILYLOXY)-TRIDECYL]-FURAN-2-YL}-PENT-4-EN-L-OL
(UK_5.6)
.
139
6.3.6.7
1
-TERT.
BUTYL
[5-(1
-TERT.
-BUTYLDIMETHYLSILYLOXYTRIDECYL)-FURAN-2-YL]-PENT-4-EN
(UK_5.7).
141
6.3.6.8
UNDEC-10-ENSAEURE-(5-[1-(TERT.-BUTYLDIMETHYLSILYLOXY-TRIDECYL)-FURAN-2-YL]
PENT-4-EN-L-YL}-ESTER
(UK_5.8)
.
143
6.3.6.9
15-{5-[1-(TERT-BUTYL-DIMETHYL-SILANYLOXY)-TRIDECYL]-FURAN-2-YL)-1-OXACYCLO
PENTADEC-LL-EN-2-ON
(UK_5.9)
.
145
6.3.7
ALTERNATIVE
SYNTHESEWEGE
.
147
6.3.7.1
5-(LL-HYDROXYUNDEC-L-INYL)-FURAN-2-CARBALDEHYD
(UK_6.1)
.
147
6.3.7.2
LL-(2-FORMYL-FURAN-5-YL)-UNDEC-10-INSAEURE
(UK_6.2)
.
148
6.3.7.3
UNDEC
1
0-INSAEUREMETHYLESTER
(UK_6.3)
.
149
6.3.7.4
1
L-(2-FORMYL-FURAN-5-YL)-UNDEC-LO-INSAEUREMETHYLESTER
(UK_6.4)
.
150
6.3.7.5
()-UNDEC-10-INSAEURE-[L-(ETHOXYCARBONYL)-ETHYL]-ESTER
(UK_6.5)
.
151
6.3.7.6
1
L-(5-FORMYL-FURAN-2-YL)-UNDEC-10-INSAEURE-[L-(ETHOXYCCU-BONYL)-ETHYL]-ESTER
(UK_6.6).
152
6.3.7.7
H-[5-(L-HYDROXYTRIDECYL)-FURAN-2-YL]-UNDEC-10-IN-L-OL
(UK_6.7)
.
154
6.3.7.8
LL-[5-(L-HYDROXYTRIDECYL)-FURAN-2-YL]-UNDEC-10-INSAEUREMETHYLESTER
(UK_6.8)
.
155
6.3.7.9
1
1-[5-(
L-HYDROXY-TRIDECYL)-FURAN-2-YL]-UNDEC-10-INSAEURE-L-ETHOXYCARBONYL
ETHYL
ESTER
(UK_6.9)
.
157
6.3.7.10
LL-HYDROXY-L-[5-(L-HYDROXYTRIDECYL)-FURAN-2-YL]-UNDECAN-L-ON
(UK_6.10)
.
158
6.3.8
IPOMEANOL-ANALOGA
.
160
6.3.8.1
L-(FURAN-3-YL)-BUT-3-EN-L-OL
(UK_7.1)
.
160
6.3.8.2
L-(FURAN-3-YL)-PENT-4-EN-L-OL
(UK_7.2)
.
161
6.3.8.3
L-(FURAN-3-YL)-PENT-4-EN-L-ON
(UK_7.3)
.
162
6.3.8.4
TRIFLUORESSIGSAEURE-[4-(FURAN-3-YL)-L-METHYL-4-OXO]-BUTYLESTER
(UK_7.4)
.
163
6.3.8.5
()-4-IPOMEANOL
(UK_7.5)
.
164
6.3.8.6
TRIFLUORESSIGSAEURE-[4-(FURAN-2-YL)-L-METHYL-4-OXO]-BUTYLESTER
(UK_7.6)
.
165
6.3.8.7
L-(FURAN-2-YL)-PENT-4-EN-L-ON
(UK_7.7)
.
166
6.3.8.8
L-(FURAN-2-YL)-4-HYDROXY-PENTAN-L-ON
(UK_7.8)
.
167
6.3.8.9
L-(FURAN-3-YL)-HEX-5-EN-L-OL
(UK_7.9)
.
168
6.3.8.10
OCTANSAEURE-[L-(FURAN-3-YL)-HEX-5-EN-L-YL]-ESTER
(UK_7.10)
.
169
6.3.8.11
OCTANSAEURE-[L-(FURAN-3-YL)-5,6-DIHYDROXY]-HEXYL-ESTER
(UK_7.1
1)
.
170
6.3.8.12
6-(FURAN-3-YI)-HEXAN-L,2,6-TRIYLTRIOCTANOAT
(UK_7.12)
.
171
6.3.8.13
5-(THIOPHEN-3-YL)-PENT-4-IN-2-OL
(UK_7.13)
.
173
6.3.8.14
4-HYDROXY-L-(THIOPHEN-3-YL)-PENTAN-L-ON
(UK_7.14)
.
174
6.4
BIOLOGISCHE
PRUEFUNG
.
175
6.4.1
AGARDIFFUSIONSTEST
.
175
6.4.1.1
TESTSUBSTANZEN
.
175
6.4.1.2
NAEHRMEDIEN
.
175
6.4.1.3
VORGEHENS
WEISE
.
176
6.4.2
MTT-ASSAY
.
176
6.4.2.1
ZELLKULTUR
.
176
6.4.3
TESTUNG
AM
NATIONAL
CANCER
INSTITUTE
.
179
6.4.3.1
ZELLKULTUR
.
179
7
LITERATURVERZEICHNIS
.
180
XIII |
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| author | Unterreitmeier, Doris 1975- |
| author_GND | (DE-588)123570492 |
| author_facet | Unterreitmeier, Doris 1975- |
| author_role | aut |
| author_sort | Unterreitmeier, Doris 1975- |
| author_variant | d u du |
| building | Verbundindex |
| bvnumber | BV022861375 |
| ctrlnum | (OCoLC)219153721 (DE-599)DNB985380608 |
| edition | 1. Aufl. |
| format | Book |
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| genre | (DE-588)4113937-9 Hochschulschrift gnd-content |
| genre_facet | Hochschulschrift |
| id | DE-604.BV022861375 |
| illustrated | Illustrated |
| index_date | 2024-07-02T18:43:45Z |
| indexdate | 2024-07-09T21:07:10Z |
| institution | BVB |
| isbn | 9783899635706 3899635701 |
| language | German |
| oai_aleph_id | oai:aleph.bib-bvb.de:BVB01-016066597 |
| oclc_num | 219153721 |
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| owner | DE-12 DE-29T DE-19 DE-BY-UBM |
| owner_facet | DE-12 DE-29T DE-19 DE-BY-UBM |
| physical | XIII, 184 S. graph. Darst. 210 mm x 148 mm, 263 gr. |
| publishDate | 2007 |
| publishDateSearch | 2007 |
| publishDateSort | 2007 |
| publisher | Hut |
| record_format | marc |
| series2 | Pharmazeutische Chemie |
| spelling | Unterreitmeier, Doris 1975- Verfasser (DE-588)123570492 aut Strukturanaloga von Annonaceen-Acetogeninen und von (+/-)-4-Ipomeanol von Doris Unterreitmeier 1. Aufl. München Hut 2007 XIII, 184 S. graph. Darst. 210 mm x 148 mm, 263 gr. txt rdacontent n rdamedia nc rdacarrier Pharmazeutische Chemie Zugl.: München, Univ., Diss., 2007. - Literaturverz. S. 180 - 182 (DE-588)4113937-9 Hochschulschrift gnd-content DNB Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=016066597&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Unterreitmeier, Doris 1975- Strukturanaloga von Annonaceen-Acetogeninen und von (+/-)-4-Ipomeanol |
| subject_GND | (DE-588)4113937-9 |
| title | Strukturanaloga von Annonaceen-Acetogeninen und von (+/-)-4-Ipomeanol |
| title_auth | Strukturanaloga von Annonaceen-Acetogeninen und von (+/-)-4-Ipomeanol |
| title_exact_search | Strukturanaloga von Annonaceen-Acetogeninen und von (+/-)-4-Ipomeanol |
| title_exact_search_txtP | Strukturanaloga von Annonaceen-Acetogeninen und von (+/-)-4-Ipomeanol |
| title_full | Strukturanaloga von Annonaceen-Acetogeninen und von (+/-)-4-Ipomeanol von Doris Unterreitmeier |
| title_fullStr | Strukturanaloga von Annonaceen-Acetogeninen und von (+/-)-4-Ipomeanol von Doris Unterreitmeier |
| title_full_unstemmed | Strukturanaloga von Annonaceen-Acetogeninen und von (+/-)-4-Ipomeanol von Doris Unterreitmeier |
| title_short | Strukturanaloga von Annonaceen-Acetogeninen und von (+/-)-4-Ipomeanol |
| title_sort | strukturanaloga von annonaceen acetogeninen und von 4 ipomeanol |
| topic_facet | Hochschulschrift |
| url | http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=016066597&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
| work_keys_str_mv | AT unterreitmeierdoris strukturanalogavonannonaceenacetogeninenundvon4ipomeanol |