Fluorescent PHD2-inhibitors for the stabilization of HIF-1α:
Gespeichert in:
| 1. Verfasser: | |
|---|---|
| Format: | Abschlussarbeit Buch |
| Sprache: | English |
| Veröffentlicht: |
Erlangen ; Nürnberg
2019
|
| Schlagworte: | |
| Online-Zugang: | Inhaltsverzeichnis Inhaltsverzeichnis |
| Beschreibung: | IV, 180 Seiten Illustrationen, Diagramme 21 cm |
Internformat
MARC
| LEADER | 00000nam a2200000 c 4500 | ||
|---|---|---|---|
| 001 | BV046180883 | ||
| 003 | DE-604 | ||
| 005 | 20210219 | ||
| 007 | t| | ||
| 008 | 191001s2019 gw a||| m||| 00||| eng d | ||
| 015 | |a 19,H10 |2 dnb | ||
| 016 | 7 | |a 1192768612 |2 DE-101 | |
| 020 | |c Broschur | ||
| 035 | |a (OCoLC)1121483060 | ||
| 035 | |a (DE-599)DNB1192768612 | ||
| 040 | |a DE-604 |b ger |e rda | ||
| 041 | 0 | |a eng | |
| 044 | |a gw |c XA-DE | ||
| 049 | |a DE-355 |a DE-29T |a DE-29 | ||
| 084 | |a 540 |2 sdnb | ||
| 100 | 1 | |a Mayer, Marleen |e Verfasser |0 (DE-588)1197763457 |4 aut | |
| 245 | 1 | 0 | |a Fluorescent PHD2-inhibitors for the stabilization of HIF-1α |c vorgelegt von Marleen Mayer |
| 246 | 1 | 3 | |a Fluoreszierende PHD2-Inhibitoren für die Stabilisierung von HIF-1α |
| 264 | 1 | |a Erlangen ; Nürnberg |c 2019 | |
| 300 | |a IV, 180 Seiten |b Illustrationen, Diagramme |c 21 cm | ||
| 336 | |b txt |2 rdacontent | ||
| 337 | |b n |2 rdamedia | ||
| 338 | |b nc |2 rdacarrier | ||
| 502 | |b Dissertation |c Friedrich-Alexander-Universität Erlangen-Nürnberg |d 2019 | ||
| 650 | 0 | 7 | |a Sauerstoffversorgung |0 (DE-588)4051815-2 |2 gnd |9 rswk-swf |
| 650 | 0 | 7 | |a Hypoxie-induzierbarer Faktor |0 (DE-588)1207298832 |2 gnd |9 rswk-swf |
| 650 | 0 | 7 | |a Regulation |0 (DE-588)4049075-0 |2 gnd |9 rswk-swf |
| 650 | 0 | 7 | |a Hypoxie |0 (DE-588)4133549-1 |2 gnd |9 rswk-swf |
| 655 | 7 | |0 (DE-588)4113937-9 |a Hochschulschrift |2 gnd-content | |
| 689 | 0 | 0 | |a Hypoxie |0 (DE-588)4133549-1 |D s |
| 689 | 0 | 1 | |a Regulation |0 (DE-588)4049075-0 |D s |
| 689 | 0 | 2 | |a Sauerstoffversorgung |0 (DE-588)4051815-2 |D s |
| 689 | 0 | |5 DE-604 | |
| 689 | 1 | 0 | |a Hypoxie-induzierbarer Faktor |0 (DE-588)1207298832 |D s |
| 689 | 1 | |5 DE-604 | |
| 856 | 4 | 2 | |m B:DE-101 |q application/pdf |u http://d-nb.info/1192768612/04 |3 Inhaltsverzeichnis |
| 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=031560423&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |3 Inhaltsverzeichnis |
| 943 | 1 | |a oai:aleph.bib-bvb.de:BVB01-031560423 | |
Datensatz im Suchindex
| _version_ | 1823841579091099648 |
|---|---|
| adam_text |
TABLE
OF
CONTENTS
1
S
TATE
OF
K
NOWLEDGE
.
1
1.1
2-OXOGLUTARATE
DEPENDENT
DIOXYGENASES
.
2
1.1.1
PROLYL-HYDROXYLASE-DOMAIN-CONTAINING
ENZYME
(PHD)
AND
FACTOR
INHIBITING
HIF(FIH)
.
5
1.2
HIF-SYSTEM
.
9
1.3
PHD
INHIBITORS
.
12
1.4
BENCHMARK
INHIBITOR
ICA
AND
ITS
APPLICATION
IN
DIFFERENT
ANIMAL
MODELSL
8
1.5
LEAD
STRUCTURES
USED
IN
THE
B
URZLAFF
GROUP
.
25
1.6
PRINCIPLES
OF
FLUORESCENCE
.
26
1.6.1
FLUORESCENCE
QUENCHING
.
29
1.6.2
STERN-VOLMER
.
33
2
O
BJECTIVE
AND
A
IMS
.
35
3
R
ESULTS
AND
D
ISCUSSION
.
37
3.1
BENZOISOQUINOLINE
BASED
INHIBITORS
.
38
3.1.1
CHLORO
SUBSTITUTED
BENZOISOQUINOLINE
INHIBITOR
(BCA)
.
39
3.1.2
METHYL
SUBSTITUTED
BENZOISOQUINOLINE
INHIBITOR
.
46
3.1.2.1
SYNTHESIS
AND
CHARACTERIZATION
OF
3-(4-(METHOXYCARBONYL)OXAZOL-5-YL)-2-
NAPHTHOIC
ACID
(1)
.
48
3.1.2.2
SYNTHESIS
AND
CHARACTERIZATION
OF
METHYL
4-HYDROXY-1
-OXO-1
,2-
DIHYDROBENZO[G]ISOQUINOLINE-3-CARBOXYLATE
(2)
.49
3.1.2.3
SYNTHESIS
AND
CHARACTERIZATION
OF
METHYL
1
-BROMO-4-HYDROXYBENZO[G]-
ISOQUINOLINE-3-CARBOXYLATE
(3)
.
50
3.1.2.4
SYNTHESIS
AND
CHARACTERIZATION
OF
METHYL
4-HYDROXY-1
-METHYL-
BENZO[G]ISOQUINOLINE-3-CARBOXYLATE
(4)
.
51
3.1.2.5
SYNTHESIS
AND
CHARACTERIZATION
OF
4-HYDROXY-1
-METHYLBENZO[G]ISO-
QUINOLINE-3-CARBOXYLIC
ACID
(5)
.
52
3.1.2.6
SYNTHESIS
AND
CHARACTERIZATION
OF
ETHYL
(4-HYDROXY-1
-METHYLBENZO[G]-
ISOQUINOLINE-3-CARBONYL)GLYCINATE
(6)
.
53
3.1.2.7
SYNTHESIS
AND
CHARACTERIZATION
OF
(4-HYDROXY-1
-METHYLBENZO[G]ISO-
QUINOLINE-3-CARBONYL)GLYCINE
(7)
.
54
3.1.3 BROMO
SUBSTITUTED
BENZOISOQUINOLINE
INHIBITOR
.
57
3.1.3.1
SYNTHESIS
AND
CHARACTERIZATION
OF
1
-BROMO-4-HYDROXY-BENZO[G]ISO-
QUINOLINE-3-CARBOXYLIC
ACID
(8)
.
58
3.1.3.2
SYNTHESIS
AND
CHARACTERIZATION
OF
ETHYL
(1-BROMO-4-HYDROXYBENZO[G]-
ISOQUINOLINE-3-CARBONYL)GLYCINATE
(9)
.
59
3.1.3.3
SYNTHESIS
AND
CHARACTERIZATION
OF
(1-BROMO-4-HYDROXYBENZO[G]ISO-
QUINOLINE-3-CARBONYL)GLYCINE
(10)
.60
3.1.4
I-ALANINE
SUBSTITUTED
BENZOISOQUINOLINE
INHIBITOR
.63
3.1.4.1
SYNTHESIS
AND
CHARACTERIZATION
OF
METHYL
1-CHLORO-4-HYDROXYBENZO[G]-
ISOQUINOLINE-3-CARBOXYLATE
(11)
.64
3.1.4.2
SYNTHESIS
AND
CHARACTERIZATION
OF
1
-CHLORO-4-HYDROXYBENZO[G]ISO-
QUINOLINE-3-CARBOXYLIC
ACID
(12)
.65
3.1.4.3
SYNTHESIS
AND
CHARACTERIZATION
OF
TERT-BUTYL
(1
-CHLORO-4-HYDROXY-
BENZO[G]ISOQUINOLINE-3-CARBONYL)-L-ALANINATE
(13)
.66
3.1.4.4
SYNTHESIS
AND
CHARACTERIZATION
OF
(1-CHLORO-4-HYDROXYBENZO[G]ISO-
QUINOLINE-3-CARBONYL)-L-ALANINE
(14)
.68
3.2
BENZOQUINOLINONE
BASED
INHIBITORS
.
72
3.2.1
BENZYL
SUBSTITUTED
BENZOQUINOLINONE
INHIBITORS
.
73
3.2.1.1
SYNTHESIS
AND
CHARACTERIZATION
OF
BENZYLIDENEAMINO-2-NAPHTHOIC
ACID
(15)
.
73
3.2.1.2
SYNTHESIS
AND
CHARACTERIZATION
OF
3-(BENZYLAMINO)-2-NAPHTHOIC
ACID
(16)
74
3.2.1.3
SYNTHESIS
AND
CHARACTERIZATION
OF
1
-BENZYL-2H-NAPHTHO[2,3-D][1,3]OXA-
ZINE-2,4(1H)-DIONE
(17)
.
75
3.2.1.4
SYNTHESIS
AND
CHARACTERIZATION
OF
ETHYL
1-BENZYL-4-HYDROXY-2-OXO-1
,2-
DIHYDROBENZO[G]QUINOLINE-3-CARBOXYLATE
(18)
.
76
3.2.1.5
SYNTHESIS
AND
CHARACTERIZATION
OF
(1-BENZYL-4-HYDROXY-2-OXO-1,2-DI-
HYDROBENZO[G]QUINOLINE-3-CARBONYL)GLYCINE
(19)
.
79
3.2.2
METHYL
SUBSTITUTED
BENZOQUINOLINONE
INHIBITOR
.
83
3.2.2.1
SYNTHESIS
AND
CHARACTERIZATION
OF
2H-NAPHTHO[2,3-D][1,3]OXAZINE-
2,4(1
H)-DIONE
(20)
.
83
3.2.2.2
SYNTHESIS
AND
CHARACTERIZATION
OF
1-METHYL-2H-NAPHTHO[2,3-D][1
,3]-
OXAZINE-2,4(1H)-DIONE
(21)
.
84
3.2.2.3
SYNTHESIS
AND
CHARACTERIZATION
OF
ETHYL
4-HYDROXY-1-METHYL-2-OXO-1
,2-
DIHYDROBENZO[G]QUINOLINE-3-CARBOXYLATE
(22)
.
85
3.22.4
SYNTHESIS
AND
CHARACTERIZATION
OF
(4-HYDROXY-1
-METHYL-2-OXO-1
,2-
DIHYDROBENZO[G]QUINOLINE-3-CARBONYL)GLYCINE
(23)
87
3.2.3
I-ALANINE
SUBSTITUTED
BENZOQUINOLINONE
INHIBITOR
89
3.2.3.2
SYNTHESIS
AND
CHARACTERIZATION
OF
(1-BENZYL-4-HYDROXY-2-OXO-1
,2-
DIHYDROBENZO[G]QUINOLINE-3-CARBONYL)-L-ALANINE
(25)
91
3.3
FLUORESCENCE
CHARACTERIZATION
94
3.3.1
QUENCHING
BEHAVIOR
WITH
FE
2+
/ZN
2+
AND
FE
3+
95
3.4
COMPARISON
OF
THE
BENZOISOQUINOLINE
AND
BENZOQUINOLINONE
INHIBITORS
.
116
4
S
UMMARY
AND
O
UTLOOK
118
5
ZUSAMMENFASSUNG
UND
AUSBLICK
123
6
E
XPERIMENTAL
S
ECTION
128
6.1
GENERAL
REMARKS
129
6.1.1
CHEMICALS
129
6.1.2
INSTRUMENTATION
130
6.2
CHARACTERIZATION
METHODS
131
6.2.1
IMMUNOBLOTTING
131
6.2.2
ICSO
DETERMINATION
133
6.2.3
LOG
ROW
134
6.2.4
QUANTUM
YIELD
DETERMINATION
135
6.2.5
FLUORESCENCE
TITRATION
AND
REVERSIBILITY
EXPERIMENTS
WITH
FE
2+
,
FE
3+
,
ZN
2+
AND
EDTA
135
6.3
SYNTHETIC
PROCEDURES
137
6.3.1
BENZOISOQUINOLINE
BASED
INHIBITORS
137
6.3.1.1
3-(4-(METHOXYCARBONYL)OXAZOL-5-YL)-2-NAPHTHOIC
ACID
(1)
137
6.3.1.2
METHYL
4-HYDROXY-1-OXO-1,2-DIHYDROBENZO[G]ISOQUINOLINE-3CARBOXYLATE
(2)
138
6.3.1.3
METHYL
1-BROMO-4-HYDROXYBENZO[G]ISOQUINOLINE-3-CARBOXYLATE
(3)
139
6.3.1.4
METHYL
4-HYDROXY-1-METHYLBENZO[G]ISOQUINOLINE-3-CARBOXYLATE
(4)
140
6.3.1.5
4-HYDROXY-1-METHYLBENZO[G]ISOQUINOLINE-3-CARBOXYLIC
ACID
(5)
141
6.3.1.6
ETHYL
(4-HYDROXY-1-METHYLBENZO[G]ISOQUINOLINE-3-CARBONYL)GLYCINATE
(6).
142
6.3.1.7
(4-HYDROXY-1-METHYLBENZO[G]ISOQUINOLINE-3-CARBONYL)GLYCINE
(7)
143
6.3.1.8
1-BROMO-4-HYDROXYBENZO[G]ISOQUINOLINE-3-CARBOXYLIC
ACID
(8)
144
III
6.3.1.9
ETHYL
(1-BROMO-4-HYDROXYBENZO[G]ISOQUINOLINE-3-CARBONYL)GLYCINATE
(9).
145
6.3.1.10
(1-BROMO-4-HYDROXYBENZO[G]ISOQUINOLINE-3-CARBONYL)GLYCINE
(10)
.
146
6.3.1.11
METHYL
1-CHLORO-4-HYDROXYBENZO[G]ISOQUINOLINE-3-CARBOXYLATE
(11)
.
147
6.3.1.12
1-CHLORO-4-HYDROXYBENZO[G]ISOQUINOLINE-3-CARBOXYLIC
ACID
(12)
.
148
6.3.1.13
TERT-BUTYL
(1-CHLORO-4-HYDROXYBENZO[G]ISOQUINOLINE-3-CARBONYL)-L-
ALANINATE
(13)
.
149
6.3.1.14
(1-CHLORO-4-HYDROXYBENZO[G]ISOQUINOLINE-3-CARBONYL)-L-ALANINE
(14).
150
6.3.2
BENZOQUINOLINONE
BASED
INHIBITORS
.
151
6.3.2.1
BENZYLIDENEAMINO-2-NAPHTHOIC
ACID
(15)
.
151
6.3.2.2
3-(BENZYLAMINO)-2-NAPHTHOIC
ACID
(16)
.
152
6.3.2
3
1-BENZYL-2H-NAPHTHO[2,3-D][1,3]OXAZINE-2,4(1
H)-DIONE
(17)
.
153
6.3.24
ETHYL
1
-BENZYL-4-HYDROXY-2-OXO-1,2-DIHYDROBENZO[G]QUINOLINE-3-
CARBOXYLATE
(18)
.
154
6.3.2.5
(1-BENZYL-4-HYDROXY-2-OXO-1,2-DIHYDROBENZO[G]QUINOLINE-3-
CARBONYL)GLYCINE
(19)
.
156
6.3.2
6
2H-NAPHTHO[2,3-D][1,3]OXAZINE-2,4(1
H)-DIONE
(20)
.
157
6.3.2
7
1-METHYL-2H-NAPHTHO[2,3-D][1,3]OXAZINE-2,4(1H)-DIONE
(21)
.
158
6.3.2.8
ETHYL
4-HYDROXY-1
-METHYL-2-OXO-1,2-DIHYDROBENZO[G]QUINOLINE-3-
CARBOXYLATE
(22)
.
159
6.3.2.9
(4-HYDROXY-1
-METHYL-2-OXO-1,2-DIHYDROBENZO[G]QUINOLINE-3-CARBONYL)-
GLYCINE
(23)
.
160
6.3.2.10
TERT-
BUTYL
(1-BENZYL-4-HYDROXY-2-OXO-1,2-DIHYDROBENZO[G]QUINOLINE-3-
CARBONYL)-L-ALANINATE
(24)
.
161
6.3.2.11
(1-BENZYL-4-HYDROXY-2-OXO-1,2-DIHYDROBENZO[G]QUINOLINE-3-CARBONYL)-L-
ALANINE
(25)
.
162
7
A
PPENDIX
.
164
7.1
DETAILS
OF
THE
STRUCTURE
DETERMINATIONS
.
165
7.2
LIST
OF
ABBREVIATIONS
AND
SYMBOLS
.
167
8
B
IBLIOGRAPHY
.
.
171
IV |
| any_adam_object | 1 |
| author | Mayer, Marleen |
| author_GND | (DE-588)1197763457 |
| author_facet | Mayer, Marleen |
| author_role | aut |
| author_sort | Mayer, Marleen |
| author_variant | m m mm |
| building | Verbundindex |
| bvnumber | BV046180883 |
| ctrlnum | (OCoLC)1121483060 (DE-599)DNB1192768612 |
| discipline | Chemie / Pharmazie |
| format | Thesis Book |
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| genre | (DE-588)4113937-9 Hochschulschrift gnd-content |
| genre_facet | Hochschulschrift |
| id | DE-604.BV046180883 |
| illustrated | Illustrated |
| indexdate | 2025-02-12T09:01:11Z |
| institution | BVB |
| language | English |
| oai_aleph_id | oai:aleph.bib-bvb.de:BVB01-031560423 |
| oclc_num | 1121483060 |
| open_access_boolean | |
| owner | DE-355 DE-BY-UBR DE-29T DE-29 |
| owner_facet | DE-355 DE-BY-UBR DE-29T DE-29 |
| physical | IV, 180 Seiten Illustrationen, Diagramme 21 cm |
| publishDate | 2019 |
| publishDateSearch | 2019 |
| publishDateSort | 2019 |
| record_format | marc |
| spelling | Mayer, Marleen Verfasser (DE-588)1197763457 aut Fluorescent PHD2-inhibitors for the stabilization of HIF-1α vorgelegt von Marleen Mayer Fluoreszierende PHD2-Inhibitoren für die Stabilisierung von HIF-1α Erlangen ; Nürnberg 2019 IV, 180 Seiten Illustrationen, Diagramme 21 cm txt rdacontent n rdamedia nc rdacarrier Dissertation Friedrich-Alexander-Universität Erlangen-Nürnberg 2019 Sauerstoffversorgung (DE-588)4051815-2 gnd rswk-swf Hypoxie-induzierbarer Faktor (DE-588)1207298832 gnd rswk-swf Regulation (DE-588)4049075-0 gnd rswk-swf Hypoxie (DE-588)4133549-1 gnd rswk-swf (DE-588)4113937-9 Hochschulschrift gnd-content Hypoxie (DE-588)4133549-1 s Regulation (DE-588)4049075-0 s Sauerstoffversorgung (DE-588)4051815-2 s DE-604 Hypoxie-induzierbarer Faktor (DE-588)1207298832 s B:DE-101 application/pdf http://d-nb.info/1192768612/04 Inhaltsverzeichnis DNB Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=031560423&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Mayer, Marleen Fluorescent PHD2-inhibitors for the stabilization of HIF-1α Sauerstoffversorgung (DE-588)4051815-2 gnd Hypoxie-induzierbarer Faktor (DE-588)1207298832 gnd Regulation (DE-588)4049075-0 gnd Hypoxie (DE-588)4133549-1 gnd |
| subject_GND | (DE-588)4051815-2 (DE-588)1207298832 (DE-588)4049075-0 (DE-588)4133549-1 (DE-588)4113937-9 |
| title | Fluorescent PHD2-inhibitors for the stabilization of HIF-1α |
| title_alt | Fluoreszierende PHD2-Inhibitoren für die Stabilisierung von HIF-1α |
| title_auth | Fluorescent PHD2-inhibitors for the stabilization of HIF-1α |
| title_exact_search | Fluorescent PHD2-inhibitors for the stabilization of HIF-1α |
| title_full | Fluorescent PHD2-inhibitors for the stabilization of HIF-1α vorgelegt von Marleen Mayer |
| title_fullStr | Fluorescent PHD2-inhibitors for the stabilization of HIF-1α vorgelegt von Marleen Mayer |
| title_full_unstemmed | Fluorescent PHD2-inhibitors for the stabilization of HIF-1α vorgelegt von Marleen Mayer |
| title_short | Fluorescent PHD2-inhibitors for the stabilization of HIF-1α |
| title_sort | fluorescent phd2 inhibitors for the stabilization of hif 1α |
| topic | Sauerstoffversorgung (DE-588)4051815-2 gnd Hypoxie-induzierbarer Faktor (DE-588)1207298832 gnd Regulation (DE-588)4049075-0 gnd Hypoxie (DE-588)4133549-1 gnd |
| topic_facet | Sauerstoffversorgung Hypoxie-induzierbarer Faktor Regulation Hypoxie Hochschulschrift |
| url | http://d-nb.info/1192768612/04 http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=031560423&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
| work_keys_str_mv | AT mayermarleen fluorescentphd2inhibitorsforthestabilizationofhif1a AT mayermarleen fluoreszierendephd2inhibitorenfurdiestabilisierungvonhif1a |
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