Azasecosteroids as new ergosterol biosynthesis inhibitors:
Gespeichert in:
| 1. Verfasser: | |
|---|---|
| Format: | Buch |
| Sprache: | English |
| Veröffentlicht: |
München
Verl. Dr. Hut
2003
|
| Ausgabe: | 1. Aufl. |
| Schriftenreihe: | Pharmazeutische Chemie
|
| Schlagworte: | |
| Online-Zugang: | Inhaltsverzeichnis |
| Beschreibung: | Zugl.: München, Univ., Diss., 2003 |
| Beschreibung: | 162 S. graph. Darst. |
| ISBN: | 389963019X |
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Datensatz im Suchindex
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| adam_text | IMAGE 1
DISSERTATION ZUR ERLANGUNG DES DOKTORGRADES
DER FAKULTAT FUR CHEMIE UND PHARMAZIE
DER LUDWIG-MAXIMILIANS-UNIVERSITAT MUNCHEN
AZASECOSTEROIDS AS NEW ERGOSTEROL
BIOSYNTHESIS INHIBITORS
VON
NOUHA SALMAN
AUS
DAMASKUS, SYRIEN
2003
IMAGE 2
CONTENT
CONTENT
GENERAL PART
A INTRODUCTION 2
1 CLINICALLY APPLIED ANTIFUNGAL AGENTS 2
1.1 STEROL BIOSYNTHESIS INHIBITORS (SBI) 2
1.1.1 ALLYLAMINES 4
1.1.2 AZOLES 4
1.1.3 MORPHOLINES 5
1.2 POLYENES 6
1.3 OTHER ANTIFUNGAL AGENTS 8
2 THE SEARCH FOR NEW ANTIFUNGAL AGENTS 9
2.1 NATURAL PRODUCTS 9
2.1.1 NEW INHIBITORS OF CELL WALL BIOSYNTHESIS 9
2.1.2 INHIBITORS OF FUNGAL PROTEIN AND AMINO ACID SYNTHESIS 10
2.1.3 OTHER INHIBITORS 10
2.2 STEROL BIOSYNTHESIS INHIBITORS 11
2.2.1 THE AZOLES 11
2.2.2 AZASTEROIDS AND AZASECOSTEROIDS AS HEI ANALOGUES 12
B AIM OF THE WORK 16
1 THE TARGET 16
2 THE STRATEGY 19
2.1 GENERAL BASIC STEPS 19
2.2 SYNTHESIS OF DIFFERENT 3-SUBSTITUTED 2-AZABICYCLO[5.3.0]DECANES 20
2.3 ATTACHMENT OF A THIRD RING WHICH RESEMBLES RING B 21
2.4 SYNTHESIS OF 2-AZABICYCLO[4.3.0]NONANES 23
C SYNTHESES 24
1 GENERAL BASIC STEPS 24
1.1 SYNTHESIS OF LACTAM 8 24
1.2 ESCHENMOSER ALKENYLATION 24
1.2.1 THE THIONATION 25
1.2.2 THE ESCHENMOSER ALKENYLATION 26
IMAGE 3
CONTENT
1.3 REDUCTION OF ENAMINES 28
1.4 W-SUBSTITUTED 2-AZABICYCLO[5.3.0]DECANES 34
2 SYNTHESIS OF DIFFERENT 3-SUBSTITUTED 2-AZABICYCLO[5.3.0]DECANES 37
2.1 3-AMINOETHYL-2-AZABICYCLO[5.3.0]DECANES 37
2.2 ALCOHOLS, THIOLS AND OTHER DERIVATIVES 41
2.2.1 ALCOHOLS 41
2.2.2 THIOLS 41
2.2.3 ENOL ETHERS, KETONES AND PYRIDAZINYL DERIVATIVES 43
2.2.3. 1 SYNTHESIS OF ENOL ETHERS AND KETONES USING TEBBE S REAGENT 43
2.2.3.2 SYNTHESIS OF PYRIDAZINYL DERIVATIVES USING THE INVERSE TYPE
HETERO DIELS- ALDER REACTION 44
3 ATTACHMENT OF A THIRD RING WHICH RESEMBLES RING B 48
4 SYNTHESIS OF 2-AZABICYCLO[4.3.0]NONANES 53
D BIOLOGICAL TESTING 61
1 TESTING SYSTEM 61
2 TESTING RESULTS 65
3 STRUCTURE-ACTIVITY RELATIONSHIPS 70
E CONCLUSION 75
EXPERIMENTAL PART
A GENERAL INFORMATION 86
1 ANALYTICAL DATA AND APPARATUS 86
2 GENERAL NOTES 86
3 ESCFIENMOSER S ALKENYTATION GENERAL PROCEDURE 87
B SYNTHESIS OF DIFFERENT SUBSTITUTED 2-AZABICYCLO[5.3.0]DECANES 88
(1R,7R,8R,12R)-8-(1,5-DIMETHYLHEXYL)-7-METHYL-2-AZABICYCLO[5.3.0]DECAN-3-
THIONE(18) 88
METHYL [(1 R,7R,8R,12R)-8-(1,5-DIMETHYLHEXYL)-7-METHYL-2-
AZABICYCLO[5.3.0]DECAN-3-YLIDENE]-ACETATE(19) 89
IMAGE 4
CONTENT
METHYL [(1R,3R,7R,8R,12R)-8-(1,5-DIMETHYLHEXYL)-7-METHYL-2-
AZABICYCLO[5.3.0]DECAN-3-YL]-ACETATE (20) 90
METHYL 2-[(1R,7R,8R,12R)-8-(1,5-DIRNETHYLHEXYL)-7-METHYL-2-
AZABICYCLO[5.3.0]DECAN-3-YLIDENE]-PROPIONATE (35) 92
METHYL [(1R,3R,7R,8R,12R)-2,7-DIMETHYL-8-(1,5-DIMETHYLHEXYL)-2-
AZABICYCLO[5.3.0]DECAN-3-YL]-ACETATE (36) 94
DIMETHYL [(1R,7R,8R,12R)-8-(1,5-DIMETHYLHEXYL)-7-METHYL-2-
AZABICYCLO[5.3.0]DECAN-3-YLIDENE]-MALONATE (37) 96
(1R,3R,7R,8R,12R)-2,7-DIMETHYL-8-(1,5-DIMETHYLHEXYL)-3-(2-HYDROXY-ETHYL)-2-
AZABICYCLO[5.3.0]DECANE (40) 97
(1R,3R,7R,8R,12R)-8-(1,5-DIMETHYLHEXYL)-7-METHYL-3-(2-HYDROXY-ETHYL)-2-
AZABICYCLO[5.3.0]DECANE(41) 98
1-[(1R,7R,8R,12R)-8-(1,5-DIMETHYLHEXYL)-7-METHYL-2-AZABICYCLO[5.3.0]DECAN-3-
YLIDENE]-3,3-DIMETHYL-BUTAN-2-ONE (42) 99
2-[(1R,7R,8R,12R)-8-(1,5-DIMETHYLHEXYL)-7-METHYL-2-AZABICYCLO[5.3.0]DECAN-3-
YLIDENE]-1-PHENYL-ETHANONE (44) 100
N, /V-DIMETHYL [(1R,3R,7R,8R, 12R)-8-( 1,5-DIMETHYLHEXYL)-7-METHYL-2-
AZABICYCLO[5.3.0]DECAN-3-YL]-ACETAMIDE (47) 102
(1R,3R,7R,8R,12R)-8-(1,5-DIMETHYLHEXYL)-7-RNETHYL-3-(N,N-DIMETHYL
AMINOETHYL)-2-AZABICYCLO[5.3.0]DECANE(51) 104
/V-METHYL [(1R,7R,8R,12R)-8-(1,5-DIMETHYLHEXYL)-7-METHYL-2-
AZABICYCLO[5.3.0]DECAN-3-YLIDENE]-ACETAMIDE (52) 105
[(1R,3R,7R,8R,12R)-8-(1,5-DIMETHYLHEXYL)-7-METHYL-2-AZABICYCLO[5.3.0]DECAN-
3-YL]-PROPAN-2-ONE (53) 107
/V-METHYL [(1R,3R,7R,8R,12R)-8-(1,5-DIMETHYLHEXYL)-7-METHYL-2-
AZABICYCLO[5.3.0]DECAN-3-YL]-ACETAMIDE(54) 108
W-METHYL[(1R,3R,7R,8R,12R)-2,7-DIMETHYL-8-(1,5-DIMETHYLHEXYL)-2-
AZABICYCLO[5.3.0]DECAN-3-YL]-ACETAMIDE (55) 110
N, /V-DIMETHYL [(1R,3R,7R,8R, 12R)-2,7-DIMETHYL 8-(
1,5-DIMETHYLHEXYL)-2- AZABICYCLO[5.3.0]DECAN-3-YL]-ACETAMIDE(56) 111
[(1R,3R,7R,8R,12R)-2,7-DIMETHYL-8-(1,5-DIMETHYLHEXYL)-2-
AZABICYCLO[5.3.0]DECAN-3-YL]-PROPAN-2-ONE(57) 112
(1R,3R,7R,8R,12R)-2,7-DIMETHYL-8-(1,5-DIMETHYLHEXYL)-3-(A/-METHYL
AMINOETHYL)-2-AZABICYCLO[5.3.0]DECANE(58) 113
ETHYL [(1R,7R,8R,12R)-8-(1,5-DIMETHYLHEXYL)-7-METHYL-2-
AZABICYCLO[5.3.0]DECAN-3-YLIDENE]-ACETATE(60) 115
IMAGE 5
CONTENT
ETHYL [(1R,3R,7R,8R, 12R)-8-(1,5-DIMETHYLHEXYL)-7-METHYL-2-
AZABICYCLO[5.3.0]DECAN-3-YL]-ACETATE (61) 116
S-{2-[(1R,3R,7R,8R,12R)-2,7-DIMETHYL-8-(1,5-DIMETHYLHEXYL)-2-
AZABICYCLO[5.3.0]DECAN-3-YL]-ETHYL} THIOACETATE (62) 118
S-{2-[(1R,3R,7R,8R,12R)-8-(1,5-DIMETHYLHEXYL)-7-METHYL-2-
AZABICYCLO[5.3.0]DECAN-3-YL]-ETHYL} THIOACETATE (63) 119
2-[(1 R,3R,7R,8R, 12R)-2,7-DIMETHYL-8-(1,5-DIMETHYLHEXYL)-2-
AZABICYCLO[5.3.0]DECAN-3-YL]-ETHANETHIOL (64) 121
2-[(1 R,3R,7R,8R, 12R)-8-(1,5-DIMETHYLHEXYL)-7-METHYL-2-
AZABICYCLO[5.3.0]DECAN-3-YL]-ETHANETHIOL (65) 122
(1R,3R,7R,8R,12R)-2,7-DIMETHYL-8-(1,5-DIMETHYLHEXYL)-3-(/V,/V-DIMETHYL
AMINOETHYL)-2-AZABICYCLO[5.3.0]DECANE(68) 123
(1R,3R,7R,8R,12R)-8-(1,5-DIMETHYLHEXYL)-7-METHYL-3-(PYRIDAZIN-4-YLMETHYL)-2-
AZABICYCLO[5.3.0]DECANE (69) 125
ETHYL [(1 R,3R,7R,8R, 12R)-8-(1,5-DIMETHYLHEXYL)-2-ETHYL-7-METHYL-2-
AZABICYCLO[5.3.0]DECAN-3-YL]-ACETATE (70) 127
(1 R,3R,7R,8R, 12R)-2,7-DIMETHYL-8-(1,5-DIMETHYLHEXYL)-3-(PYRIDAZIN-4-
YLMETHYL)-2-AZABICYCLO[5.3.0]DECANE (72) 129
(1R,3R,7R,8R,12R)-8-(1,5-DIMETHYLHEXYL)-7-METHYL-3-(3,6-BIS-TRIFLOURMETHYL-
PYRIDAZIN-4-YLMETHYL)-2-AZABICYCLO[5.3.0]DECANE (73) 130
[(1R,3R,7R,8R,12R)-2,7-DIMETHYL-8-(1,5-DIMETHYLHEXY!)-2-
AZABICYCLO[5.3.0]DECAN-3-YL]-PROPAN-2-ONE OXIME (77) 132
METHYL [(1R,3R,7R,8R,12R)-2-ALLYL-8-(1,5-DIMETHYLHEXYL)-7-METHYL-2-
AZABICYCLO[5.3.0]DECAN-3-YL]-ACETATE(79) 134
(1R,7R,8R,12R)-8-(1,5-DIMETHYLHEXYL)-7-METHYL-2-AZABICYCLO[5.3.0]DECANE
(80) 136
(1R,7R,8R,12R)-2,7-DIMETHYL-8-(1,5-DIMETHYLHEXYL)-2-AZABICYCLO[5.3.0]DECANE
(81) 137
(1R,3R,7R,8R,12R)-8-(1,5-DIMETHYLHEXYL)-3-(2-METHOXYALLYL)-7-METHYL-2-
AZABICYCLO[5.3.0]DECANE(101) 139
(1R,3R,7R,8R,12R)-2,7-DIMETHYL-8-(1,5-DIMETHYLHEXYL)-3-(2-METHOXYALLYL)-2-
AZABICYCLO[5.3.0]DECANE(102) 140
METHYL [3-DIMETHYLAMINO-6-(1R-METHYL-2R-(1R,5-DIMETHYLHEXYL)-5-
METHYLAMINO-CYCLOPENTYL)]-HEXANOATE (103) 142
IMAGE 6
CONTENT
C SYNTHESIS OF DIFFERENT SUBSTITUTED DECAHYDRO-9A-AZA-CYCLOPENTA
[E]AZULENES
143
(3R,3AR,6AR,9BR)-3-[(R)1,5-DIMETHYLHEXYL]-3A-METHYL-DECAHYDRO-9A-AZA-
CYCLOPENTA[E]AZULEN-8-ONE (75) 143
(3R,3AR,6AR,8R,9BR)-3-[(R)1,5-DIMETHYLHEXYL]-3A-METHYL-DODECAHYDRO-9A-
AZA-CYCLOPENTA[E]AZULEN-8-OL (76) 144
METHYL [(3R,3AR,6AR,7S,8R,9BR)-3A,8-DIMETHYL-3-((R) 1,5-DIMETHYLHEXYL)-
DODECAHYDRO-9A-AZA-CYCLOPENTA[E]AZULEN-7-YL]-CARBOXYLATE (82) 146
D SYNTHESIS OF 2-AZABICYCLO[4.3.0]NONANES 148
(1R,7R,8R,12R)-3,3-DICHLORO-8-(1,5-DIMETHYLHEXYL)-7-METHYL-2-
AZABICYCLO[5.3.0]DECAN-3-ONE(10) 148
(1R, 7R, 8R, 12R)-3-CHLORO-8-( 1,5-DIMETHYLHEXYL )-7-METHYL-2-
AZABICYCLO[5.3.0]DECAN-3-ONE(11) 149
(1R,7R,8R,12R)-2-BENZYL-8-(1,5-DIMETHYLHEXYL)-7-METHYL-2-
AZABICYCLO[5.3.0]DECAN-3-ONE(27) 150
(1R,7R,8R,12R)-2-BENZYL-8-(1,5-DIMETHYLHEXYL)-7-METHYL-2-
AZABICYCLO[5.3.0]DECAN-3,4-DIONE-4-OXIME (30) 152
(1R,7R,8R,12R)-2-BENZYL-8-(1,5-DIMETHYLHEXYL)-7-METHYL-2-
AZABICYCLO[5.3.0]DECAN-3,4-DIONE (83) 154
METHYL [(1 R,6R, 7R, 11 R)-2-BENZYL-7-( 1,5-DIMETHYLHEXYL)-6-METHYL-2-
AZABICYCLO[4.3.0]NONAN-3-EN-3-YL]-CARBOXYLATE (86) 155
METHYL [(1R,6R,7R,11R)-2-BENZYL-7-(1,5-DIMETHYLHEXYL)-6-METHYL-2-
AZABICYCLO[4.3.0]NONAN-3-YL]-CARBOXYLATE (87) 157
REFERENCES 159
|
| any_adam_object | 1 |
| author | Salman, Nouha |
| author_facet | Salman, Nouha |
| author_role | aut |
| author_sort | Salman, Nouha |
| author_variant | n s ns |
| building | Verbundindex |
| bvnumber | BV017706761 |
| ctrlnum | (OCoLC)59081268 (DE-599)BVBBV017706761 |
| discipline | Chemie / Pharmazie |
| edition | 1. Aufl. |
| format | Book |
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| genre | (DE-588)4113937-9 Hochschulschrift gnd-content |
| genre_facet | Hochschulschrift |
| id | DE-604.BV017706761 |
| illustrated | Illustrated |
| indexdate | 2024-07-09T19:21:00Z |
| institution | BVB |
| isbn | 389963019X |
| language | English |
| oai_aleph_id | oai:aleph.bib-bvb.de:BVB01-010645420 |
| oclc_num | 59081268 |
| open_access_boolean | |
| owner | DE-19 DE-BY-UBM DE-29T DE-12 |
| owner_facet | DE-19 DE-BY-UBM DE-29T DE-12 |
| physical | 162 S. graph. Darst. |
| publishDate | 2003 |
| publishDateSearch | 2003 |
| publishDateSort | 2003 |
| publisher | Verl. Dr. Hut |
| record_format | marc |
| series2 | Pharmazeutische Chemie |
| spelling | Salman, Nouha Verfasser aut Azasecosteroids as new ergosterol biosynthesis inhibitors Nouha Salman 1. Aufl. München Verl. Dr. Hut 2003 162 S. graph. Darst. txt rdacontent n rdamedia nc rdacarrier Pharmazeutische Chemie Zugl.: München, Univ., Diss., 2003 Enzyminhibitor (DE-588)4152479-2 gnd rswk-swf Stickstofforganische Verbindungen (DE-588)4043811-9 gnd rswk-swf Ergosterin (DE-588)4306749-9 gnd rswk-swf Secosteroide (DE-588)4283313-9 gnd rswk-swf Biosynthese (DE-588)4006902-3 gnd rswk-swf (DE-588)4113937-9 Hochschulschrift gnd-content Secosteroide (DE-588)4283313-9 s Stickstofforganische Verbindungen (DE-588)4043811-9 s Enzyminhibitor (DE-588)4152479-2 s Ergosterin (DE-588)4306749-9 s Biosynthese (DE-588)4006902-3 s DE-604 GBV Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=010645420&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Salman, Nouha Azasecosteroids as new ergosterol biosynthesis inhibitors Enzyminhibitor (DE-588)4152479-2 gnd Stickstofforganische Verbindungen (DE-588)4043811-9 gnd Ergosterin (DE-588)4306749-9 gnd Secosteroide (DE-588)4283313-9 gnd Biosynthese (DE-588)4006902-3 gnd |
| subject_GND | (DE-588)4152479-2 (DE-588)4043811-9 (DE-588)4306749-9 (DE-588)4283313-9 (DE-588)4006902-3 (DE-588)4113937-9 |
| title | Azasecosteroids as new ergosterol biosynthesis inhibitors |
| title_auth | Azasecosteroids as new ergosterol biosynthesis inhibitors |
| title_exact_search | Azasecosteroids as new ergosterol biosynthesis inhibitors |
| title_full | Azasecosteroids as new ergosterol biosynthesis inhibitors Nouha Salman |
| title_fullStr | Azasecosteroids as new ergosterol biosynthesis inhibitors Nouha Salman |
| title_full_unstemmed | Azasecosteroids as new ergosterol biosynthesis inhibitors Nouha Salman |
| title_short | Azasecosteroids as new ergosterol biosynthesis inhibitors |
| title_sort | azasecosteroids as new ergosterol biosynthesis inhibitors |
| topic | Enzyminhibitor (DE-588)4152479-2 gnd Stickstofforganische Verbindungen (DE-588)4043811-9 gnd Ergosterin (DE-588)4306749-9 gnd Secosteroide (DE-588)4283313-9 gnd Biosynthese (DE-588)4006902-3 gnd |
| topic_facet | Enzyminhibitor Stickstofforganische Verbindungen Ergosterin Secosteroide Biosynthese Hochschulschrift |
| url | http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=010645420&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
| work_keys_str_mv | AT salmannouha azasecosteroidsasnewergosterolbiosynthesisinhibitors |