Synthesis, chemical characterization, and biological evaluation of novel 10-thio-substituted 1,8-dihydroxy-9(10H)-anthracenones:
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| Main Author: | |
|---|---|
| Format: | Thesis Book |
| Language: | German |
| Published: |
1996
|
| Subjects: | |
| Online Access: | Inhaltsverzeichnis |
| Physical Description: | 192 S. graph. Darst. |
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MARC
| LEADER | 00000nam a2200000 c 4500 | ||
|---|---|---|---|
| 001 | BV011067218 | ||
| 003 | DE-604 | ||
| 005 | 19961120 | ||
| 007 | t | ||
| 008 | 961119s1996 d||| m||| 00||| ger d | ||
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| 084 | |a VS 5075 |0 (DE-625)147684: |2 rvk | ||
| 100 | 1 | |a Huang, Hsu-Shan |e Verfasser |4 aut | |
| 245 | 1 | 0 | |a Synthesis, chemical characterization, and biological evaluation of novel 10-thio-substituted 1,8-dihydroxy-9(10H)-anthracenones |c presented by Hsu-Shan Huang |
| 264 | 1 | |c 1996 | |
| 300 | |a 192 S. |b graph. Darst. | ||
| 336 | |b txt |2 rdacontent | ||
| 337 | |b n |2 rdamedia | ||
| 338 | |b nc |2 rdacarrier | ||
| 502 | |a Regensburg, Univ., Diss., 1996 | ||
| 650 | 0 | 7 | |a Antipsoriatikum |0 (DE-588)4142736-1 |2 gnd |9 rswk-swf |
| 650 | 0 | 7 | |a Dithranolderivate |0 (DE-588)4255013-0 |2 gnd |9 rswk-swf |
| 650 | 0 | 7 | |a Chemische Synthese |0 (DE-588)4133806-6 |2 gnd |9 rswk-swf |
| 655 | 7 | |0 (DE-588)4113937-9 |a Hochschulschrift |2 gnd-content | |
| 689 | 0 | 0 | |a Dithranolderivate |0 (DE-588)4255013-0 |D s |
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| 943 | 1 | |a oai:aleph.bib-bvb.de:BVB01-007412809 | |
Record in the Search Index
| _version_ | 1807773636021452800 |
|---|---|
| adam_text |
CONTENTS
A
INTRODUCTION:
ANTHRALIN
AND
PSORIASIS
HISTORICAL
AND
CURRENT
PERSPECTIVES
.
1
1
HISTORY
OF
ANTHRALIN
.
1
2
CHEMISTRY
OF
ANTHRALIN
.
3
2.1
CHEMICAL
STRUCTURE
CONSIDERATION
.
3
2.2
IMPORTANCE
OF
THE
CARBONYL
AND
THE
METHYLENE
GROUP
.
6
3
PSORIASIS
.
7
3.1
PATHOGENESIS
OF
PSORIASIS
.
7
3.2
PSORIASIS
.
8
3.3
THERAPY
.
9
4
PERSPECTIVE
AND
PURPOSE
OF
THIS
THESIS
.
10
B
SYNTHESIS
.
11
1
INTRODUCTION
.
11
2
GENERAL
SYNTHESIS
AND
SPECTROSCOPIC
CHARACTERIZATION
OF
10-ALKYLTHIO
AND
10-ARYLTHIO
ANTHRALINS
.
13
2.1
INTRODUCTION
.
13
2.2
SYNTHESIS
AND
SPECTROSCOPIC
CHARACTERIZATION
OF
10-ALKYLTHIO
ANTHRALIN
DERIVATIVES
.
13
2.3
SYNTHESIS
AND
SPECTROSCOPIC
CHARACTERIZATION
OF
10-ARYLTHIO
ANTHRALIN
DERIVATIVES
.
19
2.4
SPECTROSCOPY
OF
10-BENZYLTHIO-ANTHRALIN
(29)
AND
ITS
DEUTERATED
ANALOGS
.
22
2.5
ATTEMPTED
PREPARATION
OF
L,8-DIHYDROXY-10-[(3-HYDROXYPHENYL)THIO]
9(10H)-ANTHRACENONE
.
28
2.6
INFLUENCE
OF
SOLVENT
NUCLEOPHILICITY
AND
SOLVENT
IONIZING
POWER
.
28
2.7
ATTEMPTED PREPARATION
OF
10-[(3',4',5'-TRIHYDROXYBENZYL)THIO]
L,8-DIHYDROXY-9(10()-ANTHRACENONE
.
30
2.8
ATTEMPTED
SYNTHESIS
OF
L,8-DIHYDROXY-10-[(MERCAPTOPHENYL)THIOJ
9(
10H)-ANTHRACENONES
.
32
3
SYNTHESIS
OF
SOME
10-ALKOXY
AND
10-BENZYLOXY-ANTHRALIN
DERIVATIVES
.
33
4
A
CONVENIENT
SYNTHESIS
OF
14
C-ANTHRALIN
.
35
4.1
SYNTHESIS
OF
14
C-ANTHRALIN
.
35
4.2
SYNTHESIS
OF
10-HYDROXY-4,5-DIMETHOXY-9-ANTHRACENECARBONITRILE
(42)
.
37
4.3
ATTEMPTED
DEMETHYLATION
OF
10-HYDROXY-4,5-DIMETHOXY-9-ANTHRACENE
CARBONITRILE
(42)
.
38
C
THERMAL
AND
ELECTRON
IMPACT
INDUCED
FRAGMENTATION
.
40
1
INTRODUCTION
.
40
2
ELECTRON-IMPACT
INDUCED
AND
THERMAL
DECOMPOSITION
OF
10-ARYLTHIO-ANTHRALIN
IN
THE
MASS
SPECTROMETER
.
43
2.1
INTRODUCTION
.
43
2.2
EIMS, FDMS
AND
THERMOLYSIS
OF
10-ARYLTHIO-ANTHRALINS
.
44
3
EIMS
OF
10-BENZYLTHIO-ANTHRALIN
AND
ITS
DEUTERATED
DERIVATIVES
.
52
3.1
MULTIPLE
H-REARRANGEMENTS
.
52
3.2
EIMS
STUDY
OF
L,8-DIHYDROXY-10-[(4-METHOXYBENZYL)THIO]-9(10Z/)
ANTHRACENONE
(30)
.
56
4
EIMS
OF
VARIOUS
ALKYLTHIO-ANTHRALIN
DERIVATIVES
.
60
5
EIMS
OF
10-ALKYLOXY
AND
10-BENZYLOXY-ANTHRALIN
DERIVATIVES
.
64
5.1
FRAGMENTATIONS
OF
10-ALKOXY
AND
10-BENZYLOXYANTHRALIN
RADICAL
CATIONS
.
64
D
BIOCHEMICAL
PART
.
71
1
PHARMACOLOGY
AND
MODE
OF
ACTION
.
71
1.1
INTRODUCTION
.
71
2
INHIBITION
OF
5-LIPOXYGENASE
BY
10-SUBSTITUTED
ANTHRALIN
DERIVATIVES
IN
BOVINE
POLYMORPHONUCLEAR
LEUKOCYTES
.
74
2.1
INTRODUCTION
.
74
2.2
BIOSYNTHETIC
PATHWAYS
OF
5-LIPOXYGENASE
PRODUCTS
.
74
2.3
PATHGENETIC
ROLE
OF
LIPOXYGENASE
PRODUCTS
IN
PSORIASIS
.
78
2.4
EVALUATION
OF
5-LIPOXYGENASE
INHIBITION
BY
10-THIO-SUBSTITUTED
ANTHRONES
.
78
3
EVALUATION
OF
MOUSE
EPIDERMAL
12-LIPOXYGENASE
INHIBITION
BY
10-THIO
SUBSTITUTED
ANTHRONES
.
83
3.1
INTRODUCTION
.
83
3.2
INCREASED
FORMATION
OF
12-LIPOXYGENASE
PRODUCTS
IN
PSORIASIS
.
85
3.3
EFFECTS
OF
12-LIPOXYGENASE
PRODUCTS
IN
THE
SKIN
.
86
3.4
INACTIVATION
OF
MOUSE
EPIDERMAL
12-LIPOXYGENASE
BY
10-THIO-ANTHRALIN
DERIVATIVES
.
87
4
ANTIPROLIFERATIVE
ACTIVITY
OF
OF
10-SUBSTITUTED
ANTIPSORIATIC
ANTHRONES
AGAINST
CELL
GROWTH
OF
HUMAN
KERATINOCYTES
.
91
4.1
INTRODUCTION
.
91
4.2
TEST
SYSTEM
.
91
4.3
ANTIPROLIFERATIVE
ACTIVITY
.
.93
5
LACTATE
DEHYDROGENASE
RELEASE
AS
AN
INDICATOR
OF
MEMBRANE
INJURY
IN
CULTURED
HUMAN
KERATINOCYTES
INDUCED
BY
10-SUBSTITUTED
ANTHRALIN
DERIVATIVES
.
96
5.1
INTRODUCTION
.
96
5.2
ASSAY
FOR
LDH
ACTIVITY
.
.97
6
ACIDITY
AND
STABILITY
OF
SOME
10-SUBSTITUTED
ANTHRALIN
DERIVATIVES
.
99
6.1
INTRODUCTION
.
99
6.2
RESULTS
AND
DISCUSSION
.
100
7
DETERMINATION
OF
PARTITION
COEFFICIENTS
BY
REVERSED-PHASE
HIGH-PRESSURE
LIQUID
CHROMATOGRAPHY
.
102
7.1
INTRODUCTION
.102
7.2
LOG
P
DETERMINATION
.
104
8
LIPID
PEROXIDATION
IN
MODEL
MEMBRANES
.
107
8.1
INTRODUCTION
.
107
8.2
MECHANISM
OF
LIPID
PEROXIDATION
.
112
8.3
THE
INVOLVEMENT
OF
IRON
IN
LIPID
PEROXIDATION
.
113
8.4
INHIBITION
OF
LIPID
PEROXIDATION
.
114
9
DEOXYRIBOSE
DEGRADATION
.
117
9.1
INTRODUCTION
.
117
9.2
DEOXYRIBOSE
ASSAY
AS
A
MEASURE
OF
HYDROXYL
RADICAL
GENERATION
.
119
9.3
PERFORMING
THE
DEOXYRIBOSE
ASSAY
.
120
9.4
PROOXIDANT
PROPERTIES
OF
10-SUBSTITUTED
ANTHRALIN
DERIVATIVES
.
123
10
REACTIVITY
AGAINST
THE
STABLE
FREE
RADICAL
2,2-DIPHENYL-L-PICRYLHYDRAZYL
.
126
10.1
INTRODUCTION
.
126
10.2
ANTIOXIDANT
DETERMINATION
AGAINST
DPPH
.
128
10.3
RADICAL-SCAVENGING
EFFECTS
OF
1
O-SUBSTITUTED
ANTHRALIN
DERIVATIVES
ON
DPPH
RADICAL
.
129
E
SUMMARY
.
130
F
EXPERIMENTAL
PART
.
134
1
STANDARD
EXPERIMENTAL
CONDITIONS
.134
2
SYNTHETIC
METHODS
.136
3
5-LIPOXYGENASE
ASSAY
IN
BOVINE
POLYMORPHONUCLEAR
LEUKOCYTES
.
160
3.1
REAGENTS
AND
MATERIALS
.
160
3.2
ISOLATION
OF
GRANULOCYTES
.
161
3.3
CELL
COUNTING
.162
3.4
DETERMINATION
OF
CELL
VIABILITY
.
162
3.5
INCUBATION
PROCEDURES
AND
SAMPLE
PREPARATION
.163
3.6
REVERSED-PHASE
HPLC
ANALYSIS
.163
3.7
CALCULATION
OF
IC50
.
164
4
INHIBITION
OF
MOUSE
EPIDERMAL
12-LIPOXYGENASE
.
164
4.1
REAGENTS
AND
MATERIALS
.
164
4.2
PREPARATION
OF
EPIDERMAL
HOMOGENATES
AND
WASHED
PLATELETS
.165
4.3
INCUBATION
PROCEDURES
AND
EPIDERMAL
12-LIPOXYGENASE
ASSAY
.166
4.4
REVERSED-PHASE
HPLC
ANALYSIS
.166
4.5
CALCULATION
OF
IC50
.
167
5
DEOXYRIBOSE
DEGRADATION
.
168
5.1
REAGENTS
AND
MATERIALS
.168
5.2
DEGRADATION
OF
2-DEOXY-D-RIBOSE
.
168
5.3
PREPARATION
OF
STANDARD
CALIBRATION
CURVE
OF
MDA
.
169
6
ASSAY
OF
LIPID
PEROXIDATION
IN
BOVINE
BRAIN
PHOSPHOLIPID
LIPOSOMES
.169
6.1
REAGENTS
AND
MATERIALS
.
169
6.2
ISOLATION
OF
PHOSPHOLIPIDS
FROM
BOVINE
BRAIN
.
170
6.3
PREPARATION
OF
LIPOSOMES
FROM
PHOSPHOLIPIDS
.
170
6.4
ASSAY
OF
LIPID
PEROXIDATION
.
171
6.5
INHIBITION
OF
LIPID
PEROXIDATION
.
171
7
ANTIPROLIFERATIVE
ACTIVITY
AGAINST
THE
GROWTH
OF
HUMAN
KERATINOCYTES
.172
7.1
REAGENTS
AND
MATERIALS
.172
7.2
CELL
CULTURE
AND
DETERMINATION
OF
CELL
GROWTH
.
173
7.3
48
H-TEST
.
173
7.4
CALCULATION
OF
IC50
.
173
8
DETERMINATION
OF
REDUCING
ACTIVITIES
AGAINST
DPPH
.174
8.1
REAGENTS
AND
MATERIALS
.174
8.2
REDUCTION
OF
DPPH
.
174
8.3
TLC
ANALYSIS
.175
8.4
HPLC
ANALYSIS
.
175
9
ASSAY
OF
LACTATE
DEHYDROGENASE
RELEASE
.
176
9.1
REAGENTS
ANDMATERIALS
.
176
9.2
LDH
RELEASE
.176
10
LOG
P
DETERMINATION
.
177
10.1
REAGENTS
AND
MATERIALS
.
177
10.2
PROCEDURE
.
177
10.3
PREPARATION
OF
STANDARD
CALIBRATION
AND
CALCULATION
OF
LOG
P
.
177
11
ACIDITY
AND
STABILITY
OF
SOME
10-SUBSTITUTED
ANTHRALIN
DERIVATIVES
.
178
11.1
REAGENTS
AND
MATERIALS
.
178
11.2
KINETIC
STUDIES
ON
THE
DECOMPOSITION
OF
THE
ANTHRALIN
DERIVATIVES
.178
11.3
DETERMINATION
OF
THE
PKA
VALUES
.
179
G
REFERENCES
.
180 |
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| author | Huang, Hsu-Shan |
| author_facet | Huang, Hsu-Shan |
| author_role | aut |
| author_sort | Huang, Hsu-Shan |
| author_variant | h s h hsh |
| building | Verbundindex |
| bvnumber | BV011067218 |
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| genre_facet | Hochschulschrift |
| id | DE-604.BV011067218 |
| illustrated | Illustrated |
| indexdate | 2024-08-19T00:28:04Z |
| institution | BVB |
| language | German |
| oai_aleph_id | oai:aleph.bib-bvb.de:BVB01-007412809 |
| oclc_num | 231688453 |
| open_access_boolean | |
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| physical | 192 S. graph. Darst. |
| publishDate | 1996 |
| publishDateSearch | 1996 |
| publishDateSort | 1996 |
| record_format | marc |
| spelling | Huang, Hsu-Shan Verfasser aut Synthesis, chemical characterization, and biological evaluation of novel 10-thio-substituted 1,8-dihydroxy-9(10H)-anthracenones presented by Hsu-Shan Huang 1996 192 S. graph. Darst. txt rdacontent n rdamedia nc rdacarrier Regensburg, Univ., Diss., 1996 Antipsoriatikum (DE-588)4142736-1 gnd rswk-swf Dithranolderivate (DE-588)4255013-0 gnd rswk-swf Chemische Synthese (DE-588)4133806-6 gnd rswk-swf (DE-588)4113937-9 Hochschulschrift gnd-content Dithranolderivate (DE-588)4255013-0 s Antipsoriatikum (DE-588)4142736-1 s Chemische Synthese (DE-588)4133806-6 s DE-604 DNB Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=007412809&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Huang, Hsu-Shan Synthesis, chemical characterization, and biological evaluation of novel 10-thio-substituted 1,8-dihydroxy-9(10H)-anthracenones Antipsoriatikum (DE-588)4142736-1 gnd Dithranolderivate (DE-588)4255013-0 gnd Chemische Synthese (DE-588)4133806-6 gnd |
| subject_GND | (DE-588)4142736-1 (DE-588)4255013-0 (DE-588)4133806-6 (DE-588)4113937-9 |
| title | Synthesis, chemical characterization, and biological evaluation of novel 10-thio-substituted 1,8-dihydroxy-9(10H)-anthracenones |
| title_auth | Synthesis, chemical characterization, and biological evaluation of novel 10-thio-substituted 1,8-dihydroxy-9(10H)-anthracenones |
| title_exact_search | Synthesis, chemical characterization, and biological evaluation of novel 10-thio-substituted 1,8-dihydroxy-9(10H)-anthracenones |
| title_full | Synthesis, chemical characterization, and biological evaluation of novel 10-thio-substituted 1,8-dihydroxy-9(10H)-anthracenones presented by Hsu-Shan Huang |
| title_fullStr | Synthesis, chemical characterization, and biological evaluation of novel 10-thio-substituted 1,8-dihydroxy-9(10H)-anthracenones presented by Hsu-Shan Huang |
| title_full_unstemmed | Synthesis, chemical characterization, and biological evaluation of novel 10-thio-substituted 1,8-dihydroxy-9(10H)-anthracenones presented by Hsu-Shan Huang |
| title_short | Synthesis, chemical characterization, and biological evaluation of novel 10-thio-substituted 1,8-dihydroxy-9(10H)-anthracenones |
| title_sort | synthesis chemical characterization and biological evaluation of novel 10 thio substituted 1 8 dihydroxy 9 10h anthracenones |
| topic | Antipsoriatikum (DE-588)4142736-1 gnd Dithranolderivate (DE-588)4255013-0 gnd Chemische Synthese (DE-588)4133806-6 gnd |
| topic_facet | Antipsoriatikum Dithranolderivate Chemische Synthese Hochschulschrift |
| url | http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=007412809&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
| work_keys_str_mv | AT huanghsushan synthesischemicalcharacterizationandbiologicalevaluationofnovel10thiosubstituted18dihydroxy910hanthracenones |