Small molecules as inhibitors of streptococcal hyaluronidase: a computer-assisted and multicomponent synthesis approach
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| Format: | Thesis Book |
| Language: | English |
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2012
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| Online Access: | Volltext https://nbn-resolving.org/urn:nbn:de:bvb:355-epub-270330 Inhaltsverzeichnis |
| Physical Description: | X, 517 S. Ill., graph. Darst. |
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| 100 | 1 | |a Textor, Christian |e Verfasser |4 aut | |
| 245 | 1 | 0 | |a Small molecules as inhibitors of streptococcal hyaluronidase |b a computer-assisted and multicomponent synthesis approach |c vorgelegt von Christian Textor |
| 264 | 1 | |c 2012 | |
| 300 | |a X, 517 S. |b Ill., graph. Darst. | ||
| 336 | |b txt |2 rdacontent | ||
| 337 | |b n |2 rdamedia | ||
| 338 | |b nc |2 rdacarrier | ||
| 502 | |a Regensburg, Univ., Diss., 2012 | ||
| 650 | 0 | 7 | |a Streptococcus |0 (DE-588)4183655-8 |2 gnd |9 rswk-swf |
| 650 | 0 | 7 | |a Hyaluronidasen |0 (DE-588)4204239-2 |2 gnd |9 rswk-swf |
| 650 | 0 | 7 | |a Chemische Synthese |0 (DE-588)4133806-6 |2 gnd |9 rswk-swf |
| 650 | 0 | 7 | |a Enzyminhibitor |0 (DE-588)4152479-2 |2 gnd |9 rswk-swf |
| 650 | 0 | 7 | |a Phenylindole |0 (DE-588)4174242-4 |2 gnd |9 rswk-swf |
| 650 | 0 | 7 | |a Eintopfreaktion |0 (DE-588)4254931-0 |2 gnd |9 rswk-swf |
| 655 | 7 | |0 (DE-588)4113937-9 |a Hochschulschrift |2 gnd-content | |
| 689 | 0 | 0 | |a Streptococcus |0 (DE-588)4183655-8 |D s |
| 689 | 0 | 1 | |a Hyaluronidasen |0 (DE-588)4204239-2 |D s |
| 689 | 0 | 2 | |a Enzyminhibitor |0 (DE-588)4152479-2 |D s |
| 689 | 0 | 3 | |a Phenylindole |0 (DE-588)4174242-4 |D s |
| 689 | 0 | 4 | |a Eintopfreaktion |0 (DE-588)4254931-0 |D s |
| 689 | 0 | 5 | |a Chemische Synthese |0 (DE-588)4133806-6 |D s |
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| _version_ | 1804150710025060352 |
|---|---|
| adam_text | IMAGE 1
CONTENTS
V
CONTENTS
1 INTRODUCTION 1
1.1 HYALURONIC ACID 2
1.1.1 STRUCTURE AND PHYSICOCHEMICAL PROPERTIES 2
1.1.2 HYALURONAN METABOLISM AND PHYSIOLOGICAL FUNCTIONS 3
1.2 HYALURONIDASES 3
1.2.1 PREVALENCE AND CLASSIFICATION OF HYALURONIDASES 3
1.2.2 HYALURONIDASES FROM EUKARYOTES 4
1.2.3 HYALURONIDASES FROM PROKARYOTES 5
1.2.4 HYALURONIDASE INHIBITORS 9
1.3 REFERENCES 10
2 SCOPE AND OBJECTIVES 17
3 METHODS FOR THE DETERMINATION OF HYALURONIDASE ACTIVITY 21
3.1 INTRODUCTION 22
3.2 MORGAN-ELSON ASSAY 22
3.3 TURBIDIMETRIC ASSAY 25
3.4 ADAPTATION OF TURBIDIMETRIC ASSAY FORMATS 26
3.4.1 GENERAL REQUIREMENTS 26
3.4.2 SELECTION OF ORGANIC SOLVENT 26
3.4.3 ADJUSTING THE PH VALUE FOR THE STUDY OF VARIOUS HYALURONIDASES 26
3.4.4 PLATE LAYOUT 27
3.5 EXPERIMENTAL PROCEDURES 28
3.5.1 MATERIALS AND METHODS 28
3.5.2 MORGAN-ELSON ASSAY 28
3.5.2.1 REAGENTS AND SOLUTIONS 28
3.5.2.2 INCUBATION OF TEST COMPOUNDS 29
3.5.2.3 CALCULATION OF ENZYME INHIBITION AND ICSO VALUES 29
3.5.2.4 DETERMINATION OF HYALURONIDASE ACTIVITY 30
3.5.3 TURBIDIMETRIC ASSAY 30
3.5.3.1 REAGENTS AND SOLUTIONS 30
3.5.3.2 INCUBATION OF HYALURONIDASE INHIBITORS 31
3.5.3.3 CALCULATION OF ENZYME INHIBITION AND IC50 VALUES 34
3.5.3.4 CHECKING OF COMPOUND SOLUBILITY 35
3.5.3.5 BLANK MEASUREMENTS 35
3.6 REFERENCES 36
4 ASSESSMENT AND VALIDATION OF SCREENING HITS USING A MEDIUM THROUGHPUT
ASSAY FORMAT WITH AUTOMATED DISPENSING 39
4.1 INTRODUCTION 40
4.2 VALIDATION OF THE AUTOMATED HYALURONIDASE ASSAY 41
4.2.1 PRE-SCREEN ASSAY VALIDATION 41
4.2.1.1 ASSAY INGREDIENTS 41
4.2.1.2 SIGNAL UNIFORMITY AND SIGNAL SEPARATION 42
HTTP://D-NB.INFO/1043115994
IMAGE 2
VI
CONTENTS
4.2.2 ON-SCREEN ASSAY VALIDATION 47
4.3 HIT VALIDATION 48
4.3.1 HIT ASSESSMENT 48
4.3.2 REPRESENTATION OF SCREENING DATA 49
4.4 SUMMARY 52
4.5 REFERENCES 53
5 4-AMINO-1 H-IMLDAZOLE-2(5H)-THLONES AS INHIBITORS OF BACTERIAL
HYAIURONIDASE: A COMPUTER-ASSISTED AND MUITICOMPONENT SYNTHESIS APPROACH
55
5.1 INTRODUCTION 56
5.2 SYNTHESIS AND CHARACTERIZATION OF FIRST GENERATION INHIBITORS 59
5.2.1 PARALLEL SYNTHESIS OF 1H-PYRROL-2(5H)-ONES 59
5.2.2 PARALLEL SYNTHESIS OF 4-AMINO-1 H-IMIDAZOLE-2(5H)-ONES AND
-THIONES 60 5.3 PHARMACOLOGICAL RESULTS AND DISCUSSION OF FIRST
GENERATION INHIBITORS 62 5.3.1 GENERAL CONDITIONS AND SCREENING MODE 62
5.3.2 INHIBITORY ACTIVITIES OF SCREENING COMPOUNDS ON SAGHYAL 4755 62
5.3.3 INHIBITORY ACTIVITIES OF PURIFIED COMPOUNDS ON SAGHYAUTU 64
5.3.4 INHIBITORY ACTIVITIES OF PURIFIED COMPOUNDS ON BTH 66
5.4 SYNTHESIS AND CHARACTERIZATION OF SECOND GENERATION INHIBITORS 67
5.4.1 PARALLEL SYNTHESIS OF 4-AMINO-1H-IMIDAZOLE-2(5H)-THIONES 67 5.4.2
SYNTHESIS OF 4-AMINO-5-HYDROXY-1 H-IMIDAZO1E-2(5H)-THIONES 69 5.4.3
SYNTHESIS OF 4-AMINO-5-METHYL-1 H-IMIDAZOLE-2(5H)-THIONES 72 5.4.4
SYNTHESIS OF 4-AMINO-1 H-IMIDAZOLE-2(5H)-ONES 78
5.4.5 OXIDATION OF 4-AMINO-1 H-IMIDAZOLE-2(5H)-THIONES 80
5.4.6 X-RAY STRUCTURE OF 4-AMINO-5-METHYT-1 H-IMIDAZOLE-2(5H)-THIONES 86
5.5 PHARMACOLOGICAL RESULTS AND DISCUSSION OF SECOND GENERATION
INHIBITORS 91 5.5.1 GENERAL CONDITIONS AND SCREENING MODE 91
5.5.2 INHIBITORY ACTIVITIES OF SCREENING COMPOUNDS ON SAGHYAL 475S 91
5.5.3 INHIBITORY ACTIVITIES OF PURIFIED COMPOUNDS ON SAGHYAU755 92
5.5.3.1 4-AMINO-5-HYDROXY-1H-IMIDAZOLE-2(5H)-THIONES 92
5.5.3.2 4-AMINO-5-METHYL-1 H-IMIDAZOLE-2(5H)-THIONES 96
5.5.4 INHIBITORY ACTIVITIES OF PURIFIED COMPOUNDS ON BTH 100
5.5.5 INHIBITORY ACTIVITIES OF SELECTED COMPOUNDS ON SPNHYL 100
5.6 OUTLOOK 101
5.7 SUMMARY 108
5.8 EXPERIMENTAL SECTION 109
5.8.1 GENERAL CONDITIONS 109
5.8.2 CHEMISTRY 113
5.8.2.1 PARALLEL SYNTHESIS 113
5.8.2.2 PREPARATION OF THE COMPOUNDS 5.2, 5.3, 5.6, 5.10,5.12-5.15 115
5.8.2.3 PREPARATION OF THE COMPOUNDS 5.16-5.25 117
5.8.2.4 PREPARATION OF THE COMPOUNDS 5.26-5.35 123
5.8.2.5 PREPARATION OF THE COMPOUNDS 5.36-5.70 131
5.8.2.6 PREPARATION OF THE COMPOUNDS 5.81-5.83 153
5.9 REFERENCES 158
IMAGE 3
CONTENTS
VII
6 SCREENING OF 3-AMINO SUBSTITUTED IMIDAZO [1,2-A]PYRIDINES FOR THE
INHIBITION OF STREPTOCOCCAL HYALURONIDASES 165
6.1 INTRODUCTION 166
6.2 CHEMISTRY 168
6.3 PHARMACOLOGICAL RESULTS AND DISCUSSION 170
6.3.1 GENERAL CONDITIONS AND SCREENING MODE 170
6.3.2 INHIBITORY ACTIVITIES OF SCREENING COMPOUNDS ON SAGHYAL 47K 170
6.4 OUTLOOK 173
6.5 SUMMARY 173
6.6 EXPERIMENTAL SECTION 174
6.6.1 GENERAL CONDITIONS 174
6.6.2 CHEMISTRY 174
6.6.2.1 PARALLEL SYNTHESIS 174
6.6.2.2 PREPARATION OF THE COMPOUNDS 6.1, 6.8 175
6.7 REFERENCES 176
7 SCREENING OF SYNTHETIC ORGANIC MOLECULES, NATURAL PRODUCTS AND PEPTIDE
MIMETICS OF HYALURONAN FOR HYALURONIDASE INHIBITION 179 7.1 INTRODUCTION
180
7.2 INHIBITORY ACTIVITY OF SCREENING COMPOUNDS 181
7.2.1 BENZO[B]FURANE DERIVATIVES 181
7.2.2 BENZO[I ]THIOPHENE DERIVATIVES 182
7.2.3 BENZIMIDAZOLE DERIVATIVES 184
7.2.4 ALKANOIC ACID DERIVATIVES 185
7.2.5 MISCELLANEOUS SUBSTANCES 187
7.2.6 SCREENING OF BIOACTIVE NATURAL PRODUCTS FOR HYALURONIDASE
INHIBITION 189 7.2.7 SCREENING OF (APPROVED) DRUGS FOR HYALURONIDASE
INHIBITION 190 7.2.8 PEPTIDE-BASED SUBSTANCES 192
7.2.9 CONFORMATIONAL^ RESTRICTED 2-PHENYLINDOLE DERIVATIVES 193
7.2.10 2-PHENYIINDOLECARBALDEHYDE DERIVATIVES 195
7.2.11 AF-ALKYLATED 2-PHENYLINDOLES 197
7.2.12 A/-ALKYLATED 3-METHYL-2-PHENYLINDOLE DERIVATIVES 199
7.2.13 /V-BENZYL-3-METHYL-2-PHENYLINDOLE DERIVATIVES 202
7.2.14 A/-ALKYL-3-ETHYL-2-PHENYLINDOLE DERIVATIVES 205
7.2.15 SULFAMOYLOXY-SUBSTITUTED 3-METHYL-2-PHENYLINDOLES 205
7.2.16 6,7-DICHLORO-1 H-INDOLES 208
7.3 CONCLUSION 209
7.4 EXPERIMENTAL DATA 212
7.4.1 PHARMACOLOGICAL PARAMETERS 212
7.4.2 CHEMISTRY 212
7.5 REFERENCES 213
8 2-PHENYLINDOLE DERIVATIVES AS INHIBITORS OF STREPTOCOCCAL
HYALURONIDASES.... 219
8.1 INTRODUCTION 220
8.2 CHEMISTRY 221
8.3 PHARMACOLOGICAL RESULTS AND DISCUSSION 224
IMAGE 4
VIII
CONTENTS
8.3.1 GENERAL CONDITIONS 224
8.3.2 INHIBITORY ACTIVITIES OF /V-ALKYFATED 2-PHENYLINDOLE DERIVATIVES
225 8.3.3 INHIBITORY ACTIVITY OF N-BENZYIATED 2-PHENYLINDOLE DERIVATIVES
226 8.3.4 INHIBITORY ACTIVITIES OF SELECTED COMPOUNDS ON SPNHYL 230
8.3.5 INVESTIGATION OF SELECTED INDOLE DERIVATIVES FOR ANTIPROLIFERATIVE
ACTIVITY ON MCF-7 MAMMARY CARCINOMA CELL 231
8.4 OUTLOOK 234
8.5 SUMMARY 237
8.6 EXPERIMENTAL SECTION 238
8.6.1 GENERAL CONDITIONS; 238
8.6.2 CHEMISTRY 238
8.6.2.1. PREPARATION OF THE COMPOUNDS 8.1, 8.34 238
8.6.2.2. PREPARATION OF THE COMPOUNDS 8.2A, 8.2B, 8.35-8.37 239
8.6.2.3. PREPARATION OF THE COMPOUNDS 8.44, 8.45 242
8.6.2.4. PREPARATION OF THE COMPOUNDS 8.3A-8.8A 243
8.6.2.5. PREPARATION OF THE COMPOUNDS 8.9A-8.17A, 8.12B, 8.14B, 8.17B,
8.38-8.40, 8.46 245
8.6.2.6. PREPARATION OF THE COMPOUNDS 8.18A-8.32A, 8.27B, 8.29B, 8.32B,
8.41-8.43, 8.47 253
8.7 REFERENCES 264
9 INDOLLZINES: A BIOISOSTERIC APPROACH TO INHIBITORS OF BACTERIAL
HYALURONIDASES 267
9.1 INTRODUCTION 268
9.2 COSMO SIM BASED MODELING OF BIOISOSTERIC INHIBITORS FOR SAGHYAL 475S
270 9.3 CHEMISTRY 281
9.4 PHARMACOLOGICAL RESULTS AND DISCUSSION 282
9.4. 11 GENERAL CONDITIONS 282
9.4.2 HYALURONIDASE INHIBITORY ACTIVITIES OF 2-PHENYLINDOLIZINE
DERIVATIVES 283 9.5 SUMMARY ..284
9.6 EXPERIMENTAL SECTION 285
9.6.1 GENERAL CONDITIONS 285
9.6.2 CHEMISTRY 285
9.7 REFERENCES 286
10 SUMMARY 289
A APPENDIX 1 293
A.1 ABBREVIATIONS 294
A.2 HPLC PURITY DATA 298
A.3 X-RAY CRYSTALLOGRAPHIC DATA 299
A.3.1
RAO1-(3,5-DICHLORO-4-HYDROXYPHENYL)-5-METHYT-4-(4-(TRIFLUOROMETHYL)BENZYL
AMINO)-5-(2,4,5-TRIMETHOXY-PHENYL)-1H-IMIDAZOLE-2(5H)-THIONE (5.45) 299
A.3.2 4-CHLORO-3-ETHYL-2-(4-HYDROXYPHENYL)BENZO[6]THIOPHEN-5-OL (10) 317
A.3.3 4-CHLORO-2-(2,6-DICHLORO-4-HYDROXYPHENYL)-1 -ETHYL-1 H-INDOL-6-OL
(104) 329
A.3.4 1-ETHYI-2-(4-HYDROXYPHENYL)-3-METHYL-1H-INDOL-5-OL (128) 337 A.3.5
2-(4-BROMOPHENYL)-3-METHYLINDOLIZINE-8-CARBOXYLIC ACID (9.3) 349
IMAGE 5
CONTENTS IX
B APPENDIX II 363
B.1 COMPOUND LIBRARY 364
B.1.1 COMPOUND LIBRARY OF HYAIURONIDASE INHIBITORS (LIBRARY 1) 364
B. 1.2 COMPOUND LIBRARY OF HYAIURONIDASE INHIBITORS (LIBRARY 2) 375
B.2 SCREENING PLATES ORI.HYA.1-9 378
B.2.1 STARTING MATERIALS OF PLATES ORL.HYA.1-9 378
B.2.2 MASS SPECTAL ANALYSIS OF PLATES ORI.HYA.1-9 379
B.3 SCREENING PLATES ORI.HYA.10-19 398
B.3.1 STARTING MATERIALS OF PLATES ORI.HYA.10-19 398
B.3.2 MASS SPECTRAL ANALYSIS OF PLATES ORI.HYA.10-19 399
B.4 SCREENING PLATES ORI.HYA.20-35 420
B.4.1 STARTING MATERIALS OF PLATES ORI.HYA.20-35 420
B.4.2 MASS SPECTRAL ANALYSIS OF PLATES ORI.HYA.20-35 421
B.5 SCREENING PLATES ORI.HYA.SCR.1-7 453
B.6 SCREENING PLATES ORL.HYA.44-47 467
B.6.1 STARTING MATERIALS OF PLATES ORI.HYA.44-47 467
B.6.2 MASS SPECTRAL ANALYSIS OF PLATES ORI.HYA.44-47 467
B.7 SCREENING PLATES ORI.HYA.48-54 475
B.7.1 STARTING MATERIALS ORI.HYA.48-54 475
B.7.2 MASS SPECTRAL ANALYSIS OF PLATES ORI.HYA.48-54 475
B.8 ON-SCREEN ASSAY VALIDATION 489
B.8.1 ON-SCREEN ASSAY VALIDATION FOR PLATES ORI.HYA.1-9 489
B.8.2 ON-SCREEN ASSAY VALIDATION FOR PLATES ORI.HYA.SCR.1 -7 490
B.8.3 ON-SCREEN ASSAY VALIDATION FOR PLATES ORI.HYA.44-47 491
B.8.4 ON-SCREEN ASSAY VALIDATION FOR PLATES ORI.HYA.48-54 492
B.9 PHARMACOLOGICAL RESULTS 493
B.9.1 TABULATION OF SCREENING HITS 493
B.9.2 PHARMACOLOGICAL RESULTS FOR PLATES ORI.HYA.1-9 494
B.9.3 PHARMACOLOGICAL RESULTS FOR PLATES ORI.HYA.SCR.1-7 497
B.9.4 PHARMACOLOGICAL RESULTS FOR PLATES ORI.HYA.44-47 500
B.9.5 PHARMACOLOGICAL RESULTS FOR PLATES ORI.HYA.48-54 502
B.10 PREPARATION OF THE COMPOUNDS 6.71-5.74 505
B.10.1 GENERAL PROCEDURE 505
B.10.2
1-(3,5-DICHLORO-4-HYDROXYPHENYL)-5-HYDROXY-4-[4-(TRIFLUOROMETHYL)BENZYLAMINO]-5-
(2,4,5-TRIHYDROXYPHENYL)-1H-IMIDAZOL-2(5H)-ONE (6.71) 505 B.10.3 1
-(3,5-DICHLORO-4-HYDROXYPHENYL)-5-HYDROXY-5-PHENYL-4-[4-(TRIFLUOROMETHYL)
BENZYLAMINO]-1 H-IMIDAZOL-2(5H)-ONE (5.72) 506
B. 10.4 1
-(3,5-DICHLORO-4-HYDROXYPHENYL)-5-HYDROXY-4-[4-(TRIFLUOROMETHYL)BENZYLAMINO]-5-
(2,4,5-TRIMETHOXYPHENYL)-1H-IMIDAZOL-2(5H)-ONE (6.73) 506 B.10.5
1-(3,5-DICHLORO-4-HYDROXYPHENYL)-5-HYDROXY-5-(1H-INDAZOL-5-YL)-4-[4-
(TRIFLUOROMETHYL)BENZYLAMINO]-1 H-IMIDAZOL-2(5H)-ONE (5.74) 507 B. 11
MASS SPECTRAL ANALYSIS OF THE OXIDATION OF 5.22 508
B.11.1 MOLECULAR PROPERTIES OF 5.22 AND 5.62 508
B.11.2 DOCUMENTATION OF LC-MS DATA 508
C APPENDIX III 513
C.1 SMALL SCALE EXPRESSION OF S. PNEUMONIAE, HYALURONATE LYASE 514
IMAGE 6
X CONTENTS
C.2 LARGE SCALE EXPRESSION OF S. PNEUMONIAE HYALURONATE LYASE 514 C.3
PURIFICATION OF S. PNEUMONIAE HYALURONATE LYASE 515
C.4 COLORIMETRIC HYALURONIDASE ACTIVITY ASSAY AND PROTEIN
CHARACTERIZATION 517 C.5 REFERENCES 517
|
| any_adam_object | 1 |
| author | Textor, Christian |
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| ctrlnum | (OCoLC)859390865 (DE-599)BVBBV041253799 |
| discipline | Chemie / Pharmazie |
| format | Thesis Book |
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| genre | (DE-588)4113937-9 Hochschulschrift gnd-content |
| genre_facet | Hochschulschrift |
| id | DE-604.BV041253799 |
| illustrated | Illustrated |
| indexdate | 2024-07-10T00:43:15Z |
| institution | BVB |
| language | English |
| oai_aleph_id | oai:aleph.bib-bvb.de:BVB01-026227790 |
| oclc_num | 859390865 |
| open_access_boolean | 1 |
| owner | DE-384 DE-473 DE-BY-UBG DE-703 DE-1051 DE-824 DE-29 DE-12 DE-91 DE-BY-TUM DE-19 DE-BY-UBM DE-1049 DE-92 DE-739 DE-898 DE-BY-UBR DE-355 DE-BY-UBR DE-706 DE-20 DE-1102 |
| owner_facet | DE-384 DE-473 DE-BY-UBG DE-703 DE-1051 DE-824 DE-29 DE-12 DE-91 DE-BY-TUM DE-19 DE-BY-UBM DE-1049 DE-92 DE-739 DE-898 DE-BY-UBR DE-355 DE-BY-UBR DE-706 DE-20 DE-1102 |
| physical | X, 517 S. Ill., graph. Darst. |
| psigel | ebook |
| publishDate | 2012 |
| publishDateSearch | 2012 |
| publishDateSort | 2012 |
| record_format | marc |
| spelling | Textor, Christian Verfasser aut Small molecules as inhibitors of streptococcal hyaluronidase a computer-assisted and multicomponent synthesis approach vorgelegt von Christian Textor 2012 X, 517 S. Ill., graph. Darst. txt rdacontent n rdamedia nc rdacarrier Regensburg, Univ., Diss., 2012 Streptococcus (DE-588)4183655-8 gnd rswk-swf Hyaluronidasen (DE-588)4204239-2 gnd rswk-swf Chemische Synthese (DE-588)4133806-6 gnd rswk-swf Enzyminhibitor (DE-588)4152479-2 gnd rswk-swf Phenylindole (DE-588)4174242-4 gnd rswk-swf Eintopfreaktion (DE-588)4254931-0 gnd rswk-swf (DE-588)4113937-9 Hochschulschrift gnd-content Streptococcus (DE-588)4183655-8 s Hyaluronidasen (DE-588)4204239-2 s Enzyminhibitor (DE-588)4152479-2 s Phenylindole (DE-588)4174242-4 s Eintopfreaktion (DE-588)4254931-0 s Chemische Synthese (DE-588)4133806-6 s DE-604 Erscheint auch als Online-Ausgabe urn:nbn:de:bvb:355-epub-270330 http://epub.uni-regensburg.de/27033/ Verlag kostenfrei Volltext https://nbn-resolving.org/urn:nbn:de:bvb:355-epub-270330 Resolving-System DNB Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=026227790&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Textor, Christian Small molecules as inhibitors of streptococcal hyaluronidase a computer-assisted and multicomponent synthesis approach Streptococcus (DE-588)4183655-8 gnd Hyaluronidasen (DE-588)4204239-2 gnd Chemische Synthese (DE-588)4133806-6 gnd Enzyminhibitor (DE-588)4152479-2 gnd Phenylindole (DE-588)4174242-4 gnd Eintopfreaktion (DE-588)4254931-0 gnd |
| subject_GND | (DE-588)4183655-8 (DE-588)4204239-2 (DE-588)4133806-6 (DE-588)4152479-2 (DE-588)4174242-4 (DE-588)4254931-0 (DE-588)4113937-9 |
| title | Small molecules as inhibitors of streptococcal hyaluronidase a computer-assisted and multicomponent synthesis approach |
| title_auth | Small molecules as inhibitors of streptococcal hyaluronidase a computer-assisted and multicomponent synthesis approach |
| title_exact_search | Small molecules as inhibitors of streptococcal hyaluronidase a computer-assisted and multicomponent synthesis approach |
| title_full | Small molecules as inhibitors of streptococcal hyaluronidase a computer-assisted and multicomponent synthesis approach vorgelegt von Christian Textor |
| title_fullStr | Small molecules as inhibitors of streptococcal hyaluronidase a computer-assisted and multicomponent synthesis approach vorgelegt von Christian Textor |
| title_full_unstemmed | Small molecules as inhibitors of streptococcal hyaluronidase a computer-assisted and multicomponent synthesis approach vorgelegt von Christian Textor |
| title_short | Small molecules as inhibitors of streptococcal hyaluronidase |
| title_sort | small molecules as inhibitors of streptococcal hyaluronidase a computer assisted and multicomponent synthesis approach |
| title_sub | a computer-assisted and multicomponent synthesis approach |
| topic | Streptococcus (DE-588)4183655-8 gnd Hyaluronidasen (DE-588)4204239-2 gnd Chemische Synthese (DE-588)4133806-6 gnd Enzyminhibitor (DE-588)4152479-2 gnd Phenylindole (DE-588)4174242-4 gnd Eintopfreaktion (DE-588)4254931-0 gnd |
| topic_facet | Streptococcus Hyaluronidasen Chemische Synthese Enzyminhibitor Phenylindole Eintopfreaktion Hochschulschrift |
| url | http://epub.uni-regensburg.de/27033/ https://nbn-resolving.org/urn:nbn:de:bvb:355-epub-270330 http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=026227790&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
| work_keys_str_mv | AT textorchristian smallmoleculesasinhibitorsofstreptococcalhyaluronidaseacomputerassistedandmulticomponentsynthesisapproach |