New trends in synthetic medicinal chemistry:
Saved in:
| Format: | Book |
|---|---|
| Language: | German |
| Published: |
Weinheim [u.a.]
Wiley-VCH
2000
|
| Series: | Methods and principles in medicinal chemistry
7 |
| Subjects: | |
| Online Access: | Inhaltsverzeichnis |
| Physical Description: | XV, 353 S. |
| ISBN: | 3527297995 |
Staff View
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Record in the Search Index
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| adam_text | NEW TRENDS IN SYNTHETIC MEDICINAL CHEMISTRY EDITED BY FULVIO GUALTIERI
)WILEY-VCH WEINHEIM * NEW YORK * CHICHESTER * BRISBANE * SINGAPORE *
TORONTO CONTENTS PREFACE V LIST OF CONTRIBUTORS VII 1 ORGANIC SYNTHESIS
AND MEDICINAL CHEMISTRY F. GUALTIERI 1 1.1 SETTING THE SCENE 1 1.2
CLASSICAL AND BIO-ASSISTED ORGANIC SYNTHESIS 2 1.3 NEW STRATEGIES 9 1.4
OLIGOMERS 12 1.5 CONCLUSION 15 REFERENCES 15 2 SERIES DESIGN IN
SYNTHETIC CHEMISTRY SERGIO DEMENTI, GABRIELE CRUCIANI, MANUEL PASTOR AND
TORBJORN LUNDSTEDT 17 2.1 INTRODUCTION 18 2.2 THE DESIGN APPROACH 19
2.2.1 THE MULTIVARIATE APPROACH 20 2.2.2 DESIGN IN LATENT VARIABLES 20
2.2.3 FACTORIAL DESIGNS 21 2.2.4 D-OPTIMAL DESIGNS 23 2.2.5 CLUSTER
DESIGNS 25 2.3 OPTIMIZATION 26 2.3.1 THE CARSO PROCEDURE 26 2.4 DISJOINT
PRINCIPAL PROPERTIES 27 2.5 COMBINATORIAL CHEMISTRY 28 2.6 EXAMPLES 30
2.6.1 APPLICATIONS OF DESIGN IN PPS FOR QSAR STUDIES 30 2.6.2 EXAMPLE ON
GENERAL APPLICATION OF SERIES DESIGN TECHNIQUES 31 2.6.3 COMBINATORIAL
CHEMISTRY: A DESIGN EXAMPLE 34 2.7 CONCLUSIONS 35 REFERENCES 36 X
CONTENTS 3 COMBINATORIAL CHEMISTRY VALERY V. ANTONENKO, NICOLAY V.
KULIKOV AND REZA MORTEZAEI 39 3.1 NEEDS OF THE DRUG DISCOVERY PROCESS 39
3.2 SPLIT/POOL METHOD FOR CREATING COMBINATORIAL LIBRARIES 40 3.3
ENCODED SYNTHETIC LIBRARIES 42 3.3.1 CHEMICALLY ENCODED SYNTHETIC
LIBRARIES 42 3.3.1.1 OLIGONUCLEOTIDE TAGS 43 3.3.1.2 PEPTIDETAGS 44
3.3.1.3 HALOAROMATIC BINARY CODING 44 3.3.1.4 SECONDARY AMINE BINARY
CODING 46 3.3.1.5 MASS ENCODING 49 3.3.2 NON-CHEMICAL ENCODING METHODS
50 3.3.2.1 RADIO FREQUENCY TAGS 50 3.3.2.2 LASER ENCODING 52 3.4
PARALLEL SYNTHESIS AND POSITIONAL ENCODING 53 3.4.1 LIGHT-DIRECTED
SYNTHESIS 53 3.4.2 SPOT-SYNTHESIS ON MEMBRANES 59 3.4.3 MANUAL METHODS
FOR RESIN-BASED PARALLEL SYNTHESIS 60 3.4.3.1 HITOPS SYSTEM 60 3.4.4
SYNTHESIS ON MACROSCOPIC POLYMER SUPPORTS 63 3.4.4.1 SYNTHESIS ON
MULTIPINS 63 3.4.4.2 PARALLEL SYNTHESIS IN TEA BAGS 64 3.4.4.3
SYNTHESIS ON CELLULOSE AND OTHER LAMINAR SUPPORTS 64 3.5 TOOLS FOR
INCREASING PRODUCTIVITY IN COMBINATORIAL CHEMISTRY 64 3.5.1 INSTRUMENTS
FOR SOLUTION CHEMISTRY 65 3.5.1.1 MULTIREACTOR* (ROBOSYNTHON, INC.) 65
3.5.1.2 STEM REACTO-STATIONS* (STEM CORPORATION) 66 3.5.2 MANUAL AND
SEMIAUTOMATED INSTRUMENTS FOR SOLID-PHASE CHEMISTRY .... 68 3.5.2.1
QUEST 210 (ARGONAUT TECHNOLOGIES) 68 3.5.2.2 APOS 1200 SYSTEM (RAPP
POLYMER GMBH) 69 3.5.2.3 REACTECH SYNTHESIZER (ADVANCED CHEMTECH) 71
3.5.2.4 SAS (MULTISYNTECH GMBH) 71 3.5.2.5 SYSTEMS BASED ON 96-WELL
MICROTITER FORMAT 71 3.5.3 AUTOMATIC SYSTEMS FOR SOLID-PHASE SYNTHESIS
72 3.5.3.1 AUTOMATED RAM* SYNTHESIZER (BOHDAN AUTOMATION, INC.) 72
3.5.3.2 NAUTILUS* 2400 SYNTHESIZER (ARGONAUT TECHNOLOGIES, INC.) 73
3.5.3.3 TRIDENT* SYNTHESIZER (ARGONAUT TECHNOLOGIES, INC.) 74 3.5.3.4
SYRO II SYNTHESIZER (MULTISYNTECH GMBH) 75 3.5.3.5 ADVANCED CHEMTECH
SYNTHESIZERS 75 3.5.4 HP 7686 SOLUTION-PHASE SYNTHESIZER (HEWLETT
PACKARD) 75 REFERENCES 77 CONTENTS XI 4 TUBES AND CUBES, CHIPS AND TIPS:
TOOLS FOR SOLID-PHASE ORGANIC SYNTHESIS A.W. CZARNIK 81 4.1 INTRODUCTION
81 4.2 TUBES: THE DIVERSOMER PROJECT 82 4.3 CUBES: MATRIX CHEMISTRY 85
4.4 CHIPS: RADIOFREQUENCY-TAGGED MICROREACTORS 88 4.5 TIPS:
SELF-ASSEMBLED, RANDOMLY-ORDERED MICROARRAYS 92 4.6 CONCLUSION 94
REFERENCES 95 5 STEREOSELECTIVE SYNTHESIS OF ENANTIOMERICALLY PURE DRUGS
MAURIZIO BENAGLIA, MAURO CINQUINI AND FRANCO COZZI 97 5.1 INTRODUCTION
98 5.2 CLASSIFICATION OF THE METHODS FOR THE PREPARATION OF
ENANTIOMERICALLY PURE COMPOUNDS 98 5.2.1 DEFINITION OF STEREOSELECTIVE
SYNTHESIS 98 5.2.2 CLASSIFICATION 100 5.2.2.1 STOICHIOMETRIC METHODS 100
5.2.2.1.1 CHIRAL NON-RACEMIC SUBSTRATES 100 5.2.2.1.2 CHIRAL AUXILIARY
MODIFIED SUBSTRATES 102 5.2.2.1.3 CHIRAL NON-RACEMIC AGENTS 104 5.2.2.2
KINETIC RESOLUTION 106 5.2.2.3 MULTIPLE STEREOSELECTION 108 5.2.2.4
CATALYTIC METHODS ILL 5.3 EXAMPLES OF STEREOSELECTIVE SYNTHESIS OF DRUGS
113 5.3.1 SYNTHESIS OF SANFETRINEM 113 5.3.2 SYNTHESIS OF MK-0507 115
5.3.3 SYNTHESIS OF NAPROXEN (CHIRAL AUXILIARY APPROACH) 118 5.3.4
SYNTHESIS OF DILTIAZEM 118 5.3.5 SYNTHESIS OF MK-0287 120 5.3.6
SYNTHESIS OF L-738,372 AND L-743,726 121 5.3.7 SYNTHESIS OF
(S)-PROPRANOLOL 122 5.3.8 SYNTHESISOF AN HIV-PROTEASE INHIBITOR 124
5.3.9 SYNTHESIS OF MIBEFRADIL 125 5.3.10 SYNTHESISOF NAPROXEN AND
IBUPROFEN (BY C-H BOND FORMATION) 125 5.3.11 SYNTHESIS OF A CARBAPENEM
AND PENEM PRECURSOR 127 5.3.12 SYNTHESISOF SERTRALINE 128 5.3.13
SYNTHESIS OF DEXTROMETHORPHAN 129 5.3.14 SYNTHESISOF (IS,
2R)-1-AMINOINDANOL 131 5.3.15 SYNTHESISOF A FRAGMENT OF THE HIV-PROTEASE
INHIBITOR RO-31-8959 133 5.3.16 SYNTHESIS OF (2R, 3S)-PHENYLISOSERINE,
PRECURSOR OF THE TAXOL ANDTAXOTERE SIDE CHAINS 133 XII CONTENTS 5.3.17
SYNTHESIS OF NAPROXEN (BY C-C BOND FORMATION) 134 5.4 OUTLOOK AND
CONCLUSIONS 136 REFERENCES 136 6 RESOLUTION OF ENANTIOMERS OF CHIRAL
DRUGS GOTTFRIED BLASCHKE AND BEZHAN CHANKVETADZE 139 6.1 INTRODUCTION
139 6.2 CRYSTALLIZATION 141 6.2.1 SPONTANEOUS CRYSTALLIZATION 141 6.2.2
DIASTEREOMERIC CRYSTALLIZATION 141 6.3 KINETIC RESOLUTION 144 6.4
CHROMATOGRAPHIC TECHNIQUES 147 6.4.1 GAS CHROMATOGRAPHY 147 6.4.2
HIGH-PERFORMANCE LIQUID CHROMATOGRAPHY 150 6.4.2.1 INDIRECT HPLC
ENANTIOSEPARATIONS 150 6.4.2.2 HPLC ENANTIOSEPARATIONS USING CHIRAL
ADDITIVES TO THE MOBILE PHASE . . . 151 6.4.2.3 DIRECT HPLC
ENANTIOSEPARATIONS 151 6.4.2A PREPARATIVE RESOLUTION OF ENANTIOMERS IN
LC 153 6.4.2.4.1 ELUTION BATCH CHROMATOGRAPHY 154 6.4.2.4.2 CLOSED-LOOP
RECYCLING CHROMATOGRAPHY 156 6.4.2.4.3 SIMULATED MOVING BED
CHROMATOGRAPHY 159 6.4.3 SUPERCRITICAL (SUBCRITICAL) FLUID
CHROMATOGRAPHY 164 6.5 ELECTROMIGRATION TECHNIQUES 164 6.6 RACEMIZATION
166 6.7 METHOD SELECTION STRATEGY 167 REFERENCES 169 7 BIOCATALYZED
REACTIONS ORESTE GHISALBA 175 7.1 INTRODUCTION: BIOTECHNOLOGY AND
BIOCATALYSIS 175 7.2 ADVANTAGES OF BIOCATALYSIS 176 7.3 APPLICATION
RANGE OF BIOCATALYSIS 177 7.4 SCREENING FOR BIOCATALYSTS 182 7.5
TECHNICAL ASPECTS OF BIOCATALYSIS 185 7.6 BIOCATALYSIS IN RESEARCH AND
DEVELOPMENT: ON THE ROAD TO NEW BIOPROCESSES 191 7.7 LARGE-SCALE
BIOCATALYSIS 204 7.7.1 IMMOBILIZED ENZYMES 206 7.7.2 IMMOBILIZED
(RESTING) MECROBIAL CELLS 207 7.7.3 ADDITIONAL ESTABLISHED BIOPROCESSES
DOCUMENTED BY CASE STUDIES 208 7.8 OUTLOOK 213 REFERENCES 214 CONTENTS
XIII 8 SELECTIVE GLYCOSIDATION REACTIONS AND THEIR USE IN MEDICINAL
CHEMISTRY GIUSEPPE CAPOZZI, STEFANO MENICHETTI AND CRISTINA NATIVI 221
8.1 INTRODUCTION 221 8.2 SELECTIVE PROTECTION OF CARBOHYDRATES 222 8.2.1
ACETAL DERIVATIVES 223 8.2.2 ACTIVATION VIA STANNOXANES 224 8.2.3 SILYL
DERIVATIVES 226 8.2.4 EXPERIMENTAL PROCEDURES 227 8.3 O-GLYCOSIDATION
REACTIONS 229 8.3.1 THE KOENIGS-KNORR AND RELATED METHODS 229 8.3.2 THE
GLYCAL METHOD 233 8.3.3 THE TRICHLOROACETIMIDATE METHOD 238 8.3.4 THE
RT-PENTENYL METHOD 242 8.3.5 2-DEOXY GLYCOSIDES 245 8.3.6 EXPERIMENTAL
PROCEDURES 250 8.4 CONCLUSION 255 REFERENCES 255 9 CHEMISTRY OF
ANTISENSE OLIGONUCLEOTIDES CHRISTIAN R. NOE AND LUCIUS KAUFHOLD 261 9.1
INTRODUCTORY REMARKS 262 9.2 HISTORICAL ASPECTS 262 9.2.1 NUCLEIC ACIDS
AND MOLECULAR BIOLOGY IN DRUG RESEARCH 262 9.2.2 GENE THERAPY 264 9.3
SCOPE OF THE ARTICLE 264 9.4 CRITERIA IN DEVELOPMENT OF ANTISENSE DRUGS
265 9.4.1 STRUCTURAL ASPECTS 265 9.4.2 DEFINITION OF ANTISENSE AND
SIZE OF OLIGONUCLEOTIDES 267 9.4.3 MOLECULAR TARGETS OF ANTISENSE ACTION
268 9.5 SOLID SUPPORT SYNTHESISOF OLIGONUCLEOTIDES 269 9.5.1 BUILDING
BLOCKS 270 9.5.2 SOLID SUPPORT 271 9.5.3 CYCLE OF SYNTHESIS VIA THE
PHOSPHORAMIDITE METHOD 272 9.5.4 SPECIFIC MEASURES FOR EFFICIENT
DEPROTECTION 275 9.5.5 SYNTHESIS IN LARGE SCALE 277 9.5.6
5 -3 -SYNTHESIS 277 9.6 OLIGONUCLEOTIDES WITH MODIFICATIONS OF THE
NUCLEOTIDE-LINKAGE 277 9.6.1 PHOSPHOROTHIOATES 278 9.6.2
PHOSPHORODITHIOATES 280 9.6.3 METHYLPHOSPHONATES 281 9.6.4 PHOSPHORIC
ACID TRIESTERS 281 9.6.5 PHOSPHORAMIDATES 282 XIV CONTENTS 9.6.6
PHOSPHOROBORONATES 283 9.6.7 NON-PHOSPHORUS LINKAGES 283 9.7
MODIFICATIONS OF THE NUCLEOSIDE 285 9.7.1 2-MODIFICATION OF THE SUGAR
MOIETY 285 9.7.2 MODIFIED BASES 288 9.8 PURIFICATION AND
CHARACTERIZATION OF OLIGONUCLEOTIDES 291 9.8.1 ION-EXCHANGE
CHROMATOGRAPHY 291 9.9 ANALYSIS OF OLIGONUCLEOTIDES 292 9.9.1 CAPILLARY
ELECTROPHORESIS 292 9.9.2 MASS SPECTROMETRY 295 9.9.3 P-NMR 295 9.9.4
UV SPECTROSCOPY 296 9.9.5 ORD SPECTROSCOPY 297 9.9.6 CRYSTAL STRUCTURES
OF OLIGONUCLEOTIDES 298 9.10 ANTISENSE COMPOUNDS EXHIBITING MAJOR
MODIFICATIONS 298 9.10.1 PEPTIDE NUCLEIC ACIDS 298 9.10.2 MORPHOLINO
OLIGOMERS 299 9.10.3 MODIFICATION AT THE ANOMERIC CENTER 300 9.10.4
THREE-ATOM 2-5 -LINKAGES 301 9.11 THE TRIPLE-HELIX CONCEPT 302 9.11.1
MODIFIED OLIGONUCLEOTIDES IN TRIPLE HELIX FORMATION 304 9.11.2 MINOR
GROOVE RECOGNITION BY PEPTIDES 304 9.12 SYNTHETIC METHODS FOR LIGAND
ATTACHMENT 305 9.12.1 ATTACHMENT TO NUCLEOBASES 306 9.12.2 ATTACHMENT TO
THE SUGAR 307 9.12.3 ATTACHMENT TO THE PHOSPHATE BRIDGE 307 9.13 LIGANDS
AS ENHANCERS OF ANTISENSE ACTION: EFFECTORS 308 9.13.1 TRICYCLIC RINGS
LINKED TO OLIGONUCLEOTIDES 308 9.13.2 CHELATORS LINKED TO
OLIGONUCLEOTIDES 310 9.13.3 ZWITTERIONIC OLIGONUCLEOTIDES 311 9.14
MODIFICATION OF BIOLOGICAL EFFECTS OF OLIGONUCLEOTIDES: MODULATORS 312
9.14.1 PHOSPHORYLATION OF OLIGONUCLEOTIDES 312 9.14.2 BASE-MODIFIED
NUCLEOTIDES AT DEGENERATED SITES 312 9.14.3 NATURAL ABASIC
DNA-NUCLEOTIDES AND TETRAHYDROFURAN-SPACERS 314 9.14.4 INHIBITORS OF
ENZYMATIC DEGRADATION 314 9.15 LIGANDS FOR LOCALIZATION OF
OLIGONUCLEOTIDES: DETECTORS 314 9.15.1 BIOTINYLATION OF OLIGONUCLEOTIDES
315 9.15.2 2,4-DINITROPHENYL GROUPS IN OLIGONUCLEOTIDES 316 9.15.3
FLUORESCEIN-LINKED OLIGONUCLEOTIDES 316 9.15.4 1,N 6 -ETHENOPURINES AS
FLUOROPHORES 317 9.15.5 HALOGENATED PYRIMIDINES AND PURINES AS PHOTO
CROSS-LINKERS 318 9.15.6 APPLICATIONS OF RADIOACTIVE OLIGONUCLEOTIDES
318 9.15.7 IMMOBILIZATION AND ARRAY-TECHNIQUES 318 9.16 CATALYTICALLY
ACTIVE ANTISENSE COMPOUNDS 320 9.16.1 GROUP I INTRONS 320 CONTENTS XV
9.16.2 RNASEP 321 9.16.3 VIROIDS AND VIRUSOIDS (HAMMERHEAD RIBOZYMES)
321 9.16.4 RNASE H: CHIMERIC OLIGONUCLEOTIDES 322 9.17 DRUG DELIVERY 323
9.17.1 CELLULAR UPTAKE AND INTRACELLULAR FATE OF OLIGONUCLEOTIDES 323
9.17.2 OLIGONUCLEOTIDE LIGANDS FOR IMPROVED DRUG DELIVERY 323 9.17.3
LIPOSOMES 325 9.17 A NANOPARTICLES 326 9.17.5 VIRUS CAPSIDS 327 9.18
STANDARDS OF ANTISENSE DRUG DEVELOPMENT 327 9.19 THERAPEUTIC TARGETS 330
9.20 STATE AND TENDENCIES OF INDUSTRIAL ANTISENSE DRUG DEVELOPMENT 330
9.21 CONCLUDING REMARKS 335 REFERENCES 335 INDEX 347
|
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| id | DE-604.BV012998999 |
| illustrated | Not Illustrated |
| indexdate | 2024-07-09T18:37:30Z |
| institution | BVB |
| isbn | 3527297995 |
| language | German |
| oai_aleph_id | oai:aleph.bib-bvb.de:BVB01-008858407 |
| oclc_num | 42791022 |
| open_access_boolean | |
| owner | DE-355 DE-BY-UBR DE-20 DE-29T DE-19 DE-BY-UBM |
| owner_facet | DE-355 DE-BY-UBR DE-20 DE-29T DE-19 DE-BY-UBM |
| physical | XV, 353 S. |
| publishDate | 2000 |
| publishDateSearch | 2000 |
| publishDateSort | 2000 |
| publisher | Wiley-VCH |
| record_format | marc |
| series | Methods and principles in medicinal chemistry |
| series2 | Methods and principles in medicinal chemistry |
| spelling | New trends in synthetic medicinal chemistry ed. by Fulvio Gualtieri Weinheim [u.a.] Wiley-VCH 2000 XV, 353 S. txt rdacontent n rdamedia nc rdacarrier Methods and principles in medicinal chemistry 7 Chimie pharmaceutique ram Chemistry, Pharmaceutical methods Drug Design Drugs Design Oligonucleotides Oligonucleotides, Antisense chemistry Organic compounds Synthesis Pharmaceutical Preparations chemical synthesis Pharmaceutical chemistry Arzneimitteldesign (DE-588)4278218-1 gnd rswk-swf Pharmazeutische Chemie (DE-588)4132158-3 gnd rswk-swf Pharmazeutische Chemie (DE-588)4132158-3 s Arzneimitteldesign (DE-588)4278218-1 s DE-604 Gualtieri, Fulvio Sonstige oth Methods and principles in medicinal chemistry 7 (DE-604)BV035418617 7 GBV Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=008858407&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | New trends in synthetic medicinal chemistry Methods and principles in medicinal chemistry Chimie pharmaceutique ram Chemistry, Pharmaceutical methods Drug Design Drugs Design Oligonucleotides Oligonucleotides, Antisense chemistry Organic compounds Synthesis Pharmaceutical Preparations chemical synthesis Pharmaceutical chemistry Arzneimitteldesign (DE-588)4278218-1 gnd Pharmazeutische Chemie (DE-588)4132158-3 gnd |
| subject_GND | (DE-588)4278218-1 (DE-588)4132158-3 |
| title | New trends in synthetic medicinal chemistry |
| title_auth | New trends in synthetic medicinal chemistry |
| title_exact_search | New trends in synthetic medicinal chemistry |
| title_full | New trends in synthetic medicinal chemistry ed. by Fulvio Gualtieri |
| title_fullStr | New trends in synthetic medicinal chemistry ed. by Fulvio Gualtieri |
| title_full_unstemmed | New trends in synthetic medicinal chemistry ed. by Fulvio Gualtieri |
| title_short | New trends in synthetic medicinal chemistry |
| title_sort | new trends in synthetic medicinal chemistry |
| topic | Chimie pharmaceutique ram Chemistry, Pharmaceutical methods Drug Design Drugs Design Oligonucleotides Oligonucleotides, Antisense chemistry Organic compounds Synthesis Pharmaceutical Preparations chemical synthesis Pharmaceutical chemistry Arzneimitteldesign (DE-588)4278218-1 gnd Pharmazeutische Chemie (DE-588)4132158-3 gnd |
| topic_facet | Chimie pharmaceutique Chemistry, Pharmaceutical methods Drug Design Drugs Design Oligonucleotides Oligonucleotides, Antisense chemistry Organic compounds Synthesis Pharmaceutical Preparations chemical synthesis Pharmaceutical chemistry Arzneimitteldesign Pharmazeutische Chemie |
| url | http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=008858407&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
| volume_link | (DE-604)BV035418617 |
| work_keys_str_mv | AT gualtierifulvio newtrendsinsyntheticmedicinalchemistry |