Die Chemie der Canthin-4-one:
Gespeichert in:
| 1. Verfasser: | |
|---|---|
| Format: | Abschlussarbeit Buch |
| Sprache: | German |
| Veröffentlicht: |
München
Verl. Dr. Hut
2003
|
| Schriftenreihe: | Pharmazeutische Chemie
|
| Schlagworte: | |
| Online-Zugang: | Inhaltsverzeichnis |
| Beschreibung: | Auch als: http://dnb.ddb.de.abrufbar |
| Beschreibung: | VI, 193 S. graph. Darst. |
| ISBN: | 3899630017 |
Internformat
MARC
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| 245 | 1 | 0 | |a Die Chemie der Canthin-4-one |c von Andreas Puzik |
| 264 | 1 | |a München |b Verl. Dr. Hut |c 2003 | |
| 300 | |a VI, 193 S. |b graph. Darst. | ||
| 336 | |b txt |2 rdacontent | ||
| 337 | |b n |2 rdamedia | ||
| 338 | |b nc |2 rdacarrier | ||
| 490 | 0 | |a Pharmazeutische Chemie | |
| 500 | |a Auch als: http://dnb.ddb.de.abrufbar | ||
| 502 | |a Zugl.: München, Univ., Diss., 2003 | ||
| 650 | 0 | 7 | |a Canthinonderivate |0 (DE-588)4740013-4 |2 gnd |9 rswk-swf |
| 655 | 7 | |0 (DE-588)4113937-9 |a Hochschulschrift |2 gnd-content | |
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| 999 | |a oai:aleph.bib-bvb.de:BVB01-010314444 | ||
Datensatz im Suchindex
| _version_ | 1804129981430759424 |
|---|---|
| adam_text | IMAGE 1
DISSERTATION ZUR ERLANGUNG DES DOKTORGRADES
DER FAKULTAET FUER CHEMIE UND PHARMAZIE
DER LUDWIG-MAXIMILIANS-UNIVERSITAET MUENCHEN
DIE CHEMIE DER CANTHIN-4-ONE
VON
ANDREAS PUZIK
AUS
MUENCHEN
2003
IMAGE 2
INHALTSVERZEICHNIS
INHALTSVERZEICHNIS I
1 EINLEITUNG 1
2 THEMENSTELLUNG 4
3 SYNTHESEPLANUNG 6
3.1 1-ACYL-SS-CARBOLINE + BREDERECK S REAGENZ 6
3.2 1-ACETYL-SS-CARBOLIN + AMIDACETALE (BZW. LACTAMACETALE) 7
3.3 SUBSTITUTIONSREAKTIONEN AM FERTIGEN CANTHIN-4-ON 8
3.4 DIHYDROCANTHIN-4-ON UND FOLGEPRODUKTE 9
4 ALLGEMEINER TEIL 11
4.1 SYNTHESE VON CANTHIN-4-ON 11
4.2 1-ACYL-SS-CARBOLINE + BREDERECK S REAGENZ 14
4.2.1 SYNTHESE VON TUBOFLAVIN 14
4.2.2 SYNTHESE VON 5-CARBOXY-CANTHIN-4-ON 16
4.2.3 SYNTHESE VON 5-AMINOCANTHIN-4-ON 20
4.2.4 SYNTHESE VON 3-(9H-PYRIDO[3,4-B]INDOL-1 -YL)-1 H-PYRAZOL-4- YLAMIN
23
4.2.5 SYNTHESE VON 7,9,12B-TRIAZA-BENZO[A]ACEANTHRYLEN-8-ON MITTELS
DER SKRAUP-SYNTHESE 25
4.2.6 SYNTHESE VON ARENARIN A UND ARENARIN B 26
4.2.7 SYNTHESE VON 5-BROMCANTHIN-4-ON 30
4.3 1-ACETYL-SS-CARBOLIN + AMIDACETALE (BZW. LACTAMACETALE) 30
4.3.1 SYNTHESE VON NORISOTUBOFLAVIN 30
4.3.2 ANELLIERUNGSVERSUCH MIT EINEM HARNSTOFFACETAL 31
4.3.3 ANELLIERUNGSVERSUCH MIT EINEM LACTAMACETAL 33
4.3.4 SYNTHESE VON 1 -(9H-PYRIDO[3,4-B]INDOL-1 -YL)-2-(1 -METHYL-
PYRROLIDIN-2-YL)-ETHANON 35
4.3.5 SYNTHESE VON 1-[5-(3-N-METHYLAMINOPROPYL)-PYRAZOL-3-YL]-9H-
PYRIDO[3,4-B]INDOL 36
IMAGE 3
0 INHALTSVERZEICHNIS
4.3.6 SYNTHESE VON 1 -(7-METHYL-5,6,7,8-TETRAHYDRO-4W-1,7,8A-TRIAZA-
AZULEN-2-YL)-9H-PYRIDO[3,4-B]INDOL 37
4.3.7 SYNTHESE VON 1 -[3-(3-A/-METHYLAMINOPROPYL)-1 -METHYL-1 H-
PYRAZOL-5-YL]-9H-PYRIDO[3,4-B]INDOL 39
4.3.8 SYNTHESE VON 1-[3-(3-N-METHYLAMINOPROPYL)-ISOXAZOL-5-YL]-9H-
PYRIDO[3,4-B]INDOL OA
4.4 SUBSTITUTIONSREAKTIONEN AM FERTIGEN CANTHIN-4-ON 40
4.4.1 SYNTHESE VON 5-BROMCANTHIN-4-ON 40
4.4.2 VERSUCHE ZUR SYNTHESE VON 5-LODCANTHIN-4-ON 4
4.4.3 SYNTHESE VON 5-NITROCANTHIN-4-ON
4.4.4 VERSUCHE ZUR SYNTHESE VON CANTHIN-4-ON-5-CARBOXALDEHYD 44
4.4.5 VERSUCH ZUR SYNTHESE VON 5-A/,N-DIMETHYLAMINOMETHYLCANTHIN- 4-ON
45
4.4.6 UEBERGANGSMETALL-KATALYSIERTE KUPPLUNGSREAKTIONEN 45
4.4.6.1 SYNTHESE VON 5-PHENYLCANTHIN-4-ON 4
4.4.6.2 SYNTHESE VON 5-ACETYLCANTHIN-4-ON 4
4.4.6.3 SYNTHESE VON 5-(3-HYDROXY-PROP-1-YNYL)-CANTHIN-4-ON 50
4.4.7 SUBSTITUTION VON CANTHIN-4-ON IN POSITION 2 ^
4.4.8 SYNTHESE VON 3-METHYL-4-OXO-4H-INDOLO[3,2,1-DE][1,5]-
NAPHTHYRIDIN-3-IUM-IODID 53
4.5 SYNTHESE VON DIHYDROCANTHIN-4-ON UND ANELLIERUNGSPRODUKTEN 55
4.5.1 SYNTHESE VON DIHYDROCANTHIN-4-ON 55
4.5.2 SYNTHESE VON 11-AMINO-8H-1,7B,10,12-TETRAAZA-
BENZO[E]ACEPHENANTHRYLEN 62
4.5.3 SYNTHESE VON 8W-1,7B,14-TRIAZA-DIBENZO[E,K]ACEPHENANTHRYLEN 64
4.5.4 SYNTHESE VON 1,7B,14-TRIAZA-DIBENZO[E,K]ACEPHENANTHRYLEN- 8-ON 66
4.5.5 SYNTHESE VON 5-DIMETHYLAMINOMETHYLEN-5,6-DIHYDRO-
INDOLO[3,2,1-DE][1,5]NAPHTHYRIDIN-4-ON 67
4.5.6 SYNTHESE VON 8H-1,7B,10,12-TETRAAZA-BENZO[E]ACEPHENAN-
THRYLEN 68
IMAGE 4
III
4.5.7 SYNTHESE VON 1,7B, 10,12-TETRAAZA-BENZO[E]ACEPHENANTHRYLEN- 8-ON
70
4.5.8 SYNTHESE VON N-(5,6-DIHYDRO-4H-INDOLO[3,2,1 -DE][1,5]-
NAPHTHYRIDIN-4-YL)-N ,N -DIMETHYL-ETHAN-1,2-DIAMIN 71
4.6 SONSTIGE VERBINDUNGEN 72
4.6.1 SYNTHESE VON 10-BROMCANTHIN-4-ON 72
4.6.2 SYNTHESE VON ANNOMONTIN-DERIVATEN 74
4.6.3 HYBRIDE AUS SS-CARBOLINEN UND AZOLEN - NEUE ANTIMYKOTIKA? 78
4.6.4 SYNTHESE VON 6H-LNDOLO[3,2,1-DE][1,5]NAPHTHYRIDIN 84
4.6.5 VERSUCH ZUR SYNTHESE VON 2-(2-DIMETHYLAMINO-ETHYL)-2,4,10B-
TRIAZA-FLUORANTHEN-1,3-DION 86
4.7 BIOLOGISCHE PRUEFUNG 88
4.7.1 AGAR-DIFFUSIONSTEST 88
4.7.2 CDK1/CYCLIN B-HISTON H1 KINASE-ASSAY 91
5 ZUSAMMENFASSUNG 93
5.1 CANTHIN-4-ON UND DERIVATE 93
5.2 POLYCYCLISCHE RINGSYSTEME 97
6 EXPERIMENTELLER TEIL 100
6.1 ALLGEMEINE ANGABEN 100
6.2 SYNTHESEN 101
1-ACETYL-9-METHYL-9H-PYRIDO[3,4-B]INDOL (7) 101
9-METHYLANNOMONTIN (8) 102
A/,/V-DIMETHYLANNOMONTIN (12) 104
CANTHIN-4-ON (15) 105
W-METHYLANNOMONTIN(16) 106
5-BROMCANTHIN-4-ON(17) 108
NORISOTUBOFLAVIN (18) 109
1-BUTANOYL-9H-PYRIDO[3,4-B]INDOL(19) 110
TUBOFLAVIN (20) 111
5-LODCANTHIN-4-ON(21) 113
W,A/,AT-TRIMETHYLANNOMONTIN (23) 114
W,W-DIMETHYLANNOMONTIN (24) 115
IMAGE 5
0 INHALTSVERZEICHNIS
10-NITROCANTHIN-4-ON (25) 1 17
2-ACETYLCANTHIN-4-ON (26) 118
HARMAN(30) 1 19
1-ACETYL-6-BROM-9H-PYRIDO[3,4-B]INDOL(38) 120
10-BROMCANTHIN-4-ON (39) 1 21
1-(1-ETHOXYVINYL)-9H-PYRIDO[3,4-B]INDOL(44) 123
2-BROM-1-(9H-PYRIDO[3,4-B]INDOL-1-YL)-ETHANON(45) 124
2-CYANO-1-(9H-PYRIDO[3,4-B]INDOL-1-YL)-ETHANON(46) 125
5-CYANO-CANTHIN-4-ON (47) 126
4-OXO-4H-INDOLO[3,2,1 -DE][1,5]NAPHTHYRIDIN-5-CARBONSAEURE (48) 128
1-(9H-PYRIDO[3,4-B]INDOL-1-YL)-2-DIAZO-ETHAN-1-ON(54) 129
ARENARIN A (55) 130
()-ARENARIN B (56) 132
1-BROM-9-METHYL-9/+PYRIDO[3,4-B]INDOL(60) 133
1-(1-ETHOXYVINYL)-9-METHYL-9H-PYRIDO[3,4-B]INDOL(61) 134
2-BROM-1 -(9-METHYL-9H-PYRIDO[3,4-B]INDOL-1 -YL)-ETHANON (62) 135
2-LMIDAZOL-1-YL-1-(9-METHYL-9H-PYRIDO[3,4-B]INDOL-1-YL)-ETHANON
(63) 137
2-LMIDAZOL-1-YL-1-(9-METHYL-9H-PYRIDO[3,4-B]INDOL-1-YL)-ETHANOL(64)138 1
-{1 -(2,4-DICHLOR-BENZYLOXY)-2-IMIDAZOL-1 -YL-ETHYL]-9-RNETHYL-9F+
PYRIDO[3,4-B]INDOL (66) 140
1 -(9-METHYL-9H-PYRIDO[3,4-B]INDOL-1 -YL)-2-[1,2,4]TRIAZOL-1 -YL-ETHANON
(67) 141
1 -(9-METHYL-9H-PYRIDO[3,4-B]INDOL-1 -YL)-2-[1,2,4]TRIAZOL-1 -YL-ETHANOL
(69) 142
1 -[1 -(2,4-DICHLOR-BENZYLOXY)-2-[1,2,4]TRIAZOL-1
-YL-ETHYL]-9-METHYL-9H- PYRIDO[3,4-B]INDOL (70) 144
5-ACETYLCANTHIN-4-ON (73) 145
9-ALLYL-1-(2-PHENYLETHENYL)-9H-PYRIDO[3,4-B]INDOL(75) 147
6H-LNDOLO[3,2,1-DE][1,5]NAPHTHYRIDIN(76) 148
2-[2-(9H-PYRIDOT3,4-B]INDOL-1-YL)-2-OXO-ETHYL]-ISOINDOL-1,3-DION(78).149
IMAGE 6
2-(4-OXO-4H-INDOLO[3,2,1-DE][1,5]NAPHTHYRIDIN-5-YL)-ISOINDOL-1,3-DION
(81) 150
5-AMINO-INDOLO[3,2,1-DE][1,5]NAPHTHYRIDIN-4-ON (82) 152
3-(9H-PYRIDO[3,4-B]INDOL-1-YL)-1H-PYRAZOL-4-YLAMIN(84) 153
9-(2-[1,3]DIOXOLAN-2-YL-ETHYL)-9H-PYRIDO[3,4-B]INDOL (86) 154
3-PYRIDO[3,4-B]INDOL-9YL-PROPIONALDEHYD (87) 155
5,6-DIHYDRO-4H-INDOLO[3,2,1-DE][1,5]NAPHTHYRIDIN-4-OL(90) 157
5,6-DIHYDRO-INDOLO[3,2,1-DE][1,5]NAPHTHYRIDIN-4-ON (91) 158
11 -AMINO-8H-1,7B, 10,12-TETRAAZA-BENZO[E]ACEPHENANTHRYLEN (92). 159
(/V-(2-DIMETHYLAMINO-ETHYL)-9H-PYRIDO[3,4-B]INDOL-1-CARBONSAEURE-
AMID(96) 161
7,9,12B-TRIAZA-BENZO[A]ACEANTHRYLEN-8-ON (98) 162
8H-1,7B,14-TRIAZA-DIBENZO[E,K]ACEPHENANTHRYLEN (101) 164
N-(5,6-DIHYDRO-4H-INDOLO[3,2,1-DE][1,5]NAPHTHYRIDIN-4-YL)-N N -
DIMETHYL-ETHAN-1,2-DIAMIN (105) 165
1 -(9H-PYRIDO[3,4-B]INDOL-1 -YL)-2-(1
-METHYL-PYRROLIDIN-2-YLIDEN)-ETHANON
(107) 167
1 -(9H-PYRIDO[3,4-B]INDOL-1 -YL)-2-(1 -METHYL-PYRROLIDIN-2-YL)-ETHANON
(108) 168
1-(9-ETHYL-9H-PYRIDO[3,4-B]INDOL-1-YL)-ETHANON(109) 169
1-[5-(3-N-METHYLAMINOPROPYL)-PYRAZOL-3-YL]-9H-PYRIDO[3,4-B]INDOL
(111) 171
1 -[3-(3-N-METHYLAMINOPROPYL)-1 -METHYL-1 H-PYRAZOL-5-YL]-9/+
PYRIDO[3,4-B]INDOL(112) 172
1-(7-METHYL-5,6,7,8-TETRAHYDRO-4H-1,7,8A-TRIAZA-AZULEN-2-YL)-9H-
PYRIDO[3,4-B]INDOL(114) 174
1-[3-(3-N-METHYLAMINOPROPYL)-ISOXAZOL-5-YL]-9/+PYRIDO[3,4-B]INDOL
(115) 175
9-(2-BROMETHYL)-2,3,4,9-TETRAHYDRO-PYRIDO[3,4-B]INDOL-1-ON (117) 176
3-METHYL-4-OXO-4/+INDOLO[3,2,1 -DE)[1,5]NAPHTHYRIDIN-3-IUM-IODID
(120) 178
3-(1 -BROM-PYRIDO[3,4-B]INDOL-9-YL)-PROPANSAEUREMETHYLESTER (121)... 179
IMAGE 7
0 INHALTSVERZEICHNIS
VI --
5-DIMETHYLAMINOMETHYLEN-5,6-DIHYDRO-INDOLO[3,2,1-
DE][1,5]NAPHTHYRIDIN-4-ON(124) 180
8H-1,7B,10,12-TETRAAZA-BENZO[E]ACEPHENANTHRYLEN (128) 181
1,7B,10,12-TETRAAZA-BENZO[E]ACEPHENANTHRYLEN-8-ON (129) 183
1,7B, 14-TRIAZA-DIBENZO[E,K]ACEPHENANTHRYLEN-8-ON (131) 184
5-PHENYLCANTHIN-4-ON(132) 185
5-(3-HYDROXY-PROP-1 -YNYL)-INDOLO[3,2,1 -DE][1,5]NAPHTHYRIDIN-4-ON
(133) 187
6.3 BIOLOGISCHE PRUEFUNG 188
6.3.1 AGAR-DIFFUSIONSTEST 188
6.3.2 CDK1/CYCLIN B-HISTON H1 KINASE-ASSAY 189
7 LITERATURVERZEICHNIS ....190
|
| any_adam_object | 1 |
| author | Puzik, Andreas 1972- |
| author_GND | (DE-588)124809790 |
| author_facet | Puzik, Andreas 1972- |
| author_role | aut |
| author_sort | Puzik, Andreas 1972- |
| author_variant | a p ap |
| building | Verbundindex |
| bvnumber | BV017103036 |
| ctrlnum | (OCoLC)644205957 (DE-599)BVBBV017103036 |
| format | Thesis Book |
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| genre | (DE-588)4113937-9 Hochschulschrift gnd-content |
| genre_facet | Hochschulschrift |
| id | DE-604.BV017103036 |
| illustrated | Illustrated |
| indexdate | 2024-07-09T19:13:46Z |
| institution | BVB |
| isbn | 3899630017 |
| language | German |
| oai_aleph_id | oai:aleph.bib-bvb.de:BVB01-010314444 |
| oclc_num | 644205957 |
| open_access_boolean | |
| owner | DE-19 DE-BY-UBM DE-12 DE-29T |
| owner_facet | DE-19 DE-BY-UBM DE-12 DE-29T |
| physical | VI, 193 S. graph. Darst. |
| publishDate | 2003 |
| publishDateSearch | 2003 |
| publishDateSort | 2003 |
| publisher | Verl. Dr. Hut |
| record_format | marc |
| series2 | Pharmazeutische Chemie |
| spelling | Puzik, Andreas 1972- Verfasser (DE-588)124809790 aut Die Chemie der Canthin-4-one von Andreas Puzik München Verl. Dr. Hut 2003 VI, 193 S. graph. Darst. txt rdacontent n rdamedia nc rdacarrier Pharmazeutische Chemie Auch als: http://dnb.ddb.de.abrufbar Zugl.: München, Univ., Diss., 2003 Canthinonderivate (DE-588)4740013-4 gnd rswk-swf (DE-588)4113937-9 Hochschulschrift gnd-content Canthinonderivate (DE-588)4740013-4 s DE-604 GBV Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=010314444&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Puzik, Andreas 1972- Die Chemie der Canthin-4-one Canthinonderivate (DE-588)4740013-4 gnd |
| subject_GND | (DE-588)4740013-4 (DE-588)4113937-9 |
| title | Die Chemie der Canthin-4-one |
| title_auth | Die Chemie der Canthin-4-one |
| title_exact_search | Die Chemie der Canthin-4-one |
| title_full | Die Chemie der Canthin-4-one von Andreas Puzik |
| title_fullStr | Die Chemie der Canthin-4-one von Andreas Puzik |
| title_full_unstemmed | Die Chemie der Canthin-4-one von Andreas Puzik |
| title_short | Die Chemie der Canthin-4-one |
| title_sort | die chemie der canthin 4 one |
| topic | Canthinonderivate (DE-588)4740013-4 gnd |
| topic_facet | Canthinonderivate Hochschulschrift |
| url | http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=010314444&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
| work_keys_str_mv | AT puzikandreas diechemiedercanthin4one |