Natural products in medicinal chemistry:
Gespeichert in:
| Weitere Verfasser: | |
|---|---|
| Format: | Buch |
| Sprache: | English |
| Veröffentlicht: |
Weinheim
Wiley-VCH
2014
|
| Schriftenreihe: | Methods and principles in medicinal chemistry
60 |
| Schlagworte: | |
| Online-Zugang: | Inhaltsverzeichnis |
| Beschreibung: | Includes bibliographical references and index |
| Beschreibung: | XXI, 630 S. Ill., graph. Darst. |
| ISBN: | 9783527332182 9783527676545 |
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| 245 | 1 | 0 | |a Natural products in medicinal chemistry |c ed. by Stephen Hanessian |
| 264 | 1 | |a Weinheim |b Wiley-VCH |c 2014 | |
| 300 | |a XXI, 630 S. |b Ill., graph. Darst. | ||
| 336 | |b txt |2 rdacontent | ||
| 337 | |b n |2 rdamedia | ||
| 338 | |b nc |2 rdacarrier | ||
| 490 | 1 | |a Methods and principles in medicinal chemistry |v 60 | |
| 500 | |a Includes bibliographical references and index | ||
| 650 | 4 | |a Natural products | |
| 650 | 4 | |a Organic compounds / Synthesis | |
| 650 | 4 | |a Pharmaceutical chemistry | |
| 650 | 0 | 7 | |a Organische Chemie |0 (DE-588)4043793-0 |2 gnd |9 rswk-swf |
| 650 | 0 | 7 | |a Bio-Produkt |0 (DE-588)4345488-4 |2 gnd |9 rswk-swf |
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| 689 | 0 | 1 | |a Bio-Produkt |0 (DE-588)4345488-4 |D s |
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| 700 | 1 | |a Hanessian, Stephen |0 (DE-588)172124506 |4 edt | |
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| 830 | 0 | |a Methods and principles in medicinal chemistry |v 60 |w (DE-604)BV035418617 |9 60 | |
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Datensatz im Suchindex
| _version_ | 1804152021960359936 |
|---|---|
| adam_text | CONTENTS
LIST OF CONTRIBUTORS
XV
PREFACE
XIX
PERSONAL FOREWORD
XXI
PART ONE NATURAL PRODUCTS AS SOURCES OF POTENTIAL DRUGS AND SYSTEMATIC
COMPOUND COLLECTIONS 1
1 NATURAL PRODUCTS AS DRUGS AND LEADS TO DRUGS: AN INTRODUCTION AND
PERSPECTIVE AS OF THE END OF 2012 3
DAVID
J. NEWMAN AND CORDON M. CRAGG
1.1 INTRODUCTION 3
1.2 THE SPONGE-DERIVED NUCLEOSIDE LINK TO DRUGS 5
1.3 INITIAL RECOGNITION OF MICROBIAL SECONDARY METABOLITES
AS ANTIBACTERIAL DRUGS 8
1.4 P-LACTAMS OF ALL CLASSES 9
1.5 TETRACYCLINE DERIVATIVES 12
1.6 GLYCOPEPTIDE ANTIBACTERIALS 13
1.7 LIPOPEPTIDE ANTIBACTERIALS 16
1.8 MACROLIDE ANTIBIOTICS 18
1.9 PLEUROMUTILIN DERIVATIVES 19
1.10 PRIVILEGED STRUCTURES 21
1.11 THE ORIGIN OF THE BENZODIAZEPINES 21
1.12 BENZOPYRANS: A SOURCE OF UNUSUAL ANTIBACTERIAL AND
OTHER AGENTS 22
1.13 MULTIPLE ENZYMATIC INHIBITORS FROM RELATIVELY SIMPLE NATURAL
PRODUCT SECONDARY METABOLITES 23
1.14 A VARIATION ON BIOS: THE INSIDE-OUT APPROACH 26
1.15 OTHER PRIVILEGED STRUCTURES 26
1.16 PRIVILEGED STRUCTURES AS INHIBITORS OF PROTEIN-PROTEIN
INTERACTIONS 27
1.17 UNDERPRIVILEGED SCAFFOLDS 30
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SO WHERE SHOULD ONE LOOK IN THE TWENTY-FIRST CENTURY FOR NOVEL
STRUCTURES FROM NATURAL SOURCES? 31
CONCLUSIONS 33
REFERENCES 33
NATURAL PRODUCT-DERIVED AND NATURAL PRODUCT-INSPIRED COMPOUND
COLLECTIONS 43
STEFANO RIZZO, VIJAY WAKCHAURE, AND HERBERT WALDMANN
INTRODUCTION 43
MODERN APPROACHES TO PRODUCE NATURAL PRODUCT LIBRARIES 44
PREFRACTIONATED NATURAL PRODUCT LIBRARIES 45
LIBRARIES OF PURE NATURAL PRODUCTS 46
SEMISYNTHETIC LIBRARIES OF NATURAL PRODUCT-DERIVED COMPOUNDS 46
SYNTHETIC LIBRARIES OF NATURAL PRODUCT-INSPIRED COMPOUNDS 47
SOLID-PHASE TECHNIQUES 48
SOLUTION-PHASE TECHNIQUES 50
SOLID-SUPPORTED REAGENTS AND SCAVENGERS 55
TAGGING APPROACH 58
COMPOUND COLLECTIONS WITH CARBOCYCLIC CORE STRUCTURES 60
ILLUDIN-INSPIRED COMPOUND COLLECTION 60
LAPOCHOL-INSPIRED NAPHTHOQUINONE COLLECTION 61
A COMPOUND COLLECTION WITH DECALIN CORE STRUCTURE 62
COMPOUND COLLECTIONS WITH OXA-HETEROCYCLIC SCAFFOLDS 63
CARPANONE-INSPIRED COMPOUND COLLECTION 63
CALANOLIDE-INSPIRED COMPOUND COLLECTION 64
BENZOPYRAN-INSPIRED COMPOUND COLLECTION 65
COMPOUND COLLECTIONS WITH AZA-HETEROCYCLIC SCAFFOLDS 66
SOLUTION-PHASE SYNTHESIS OF () MARINOPYRROLE A AND A
CORRESPONDING LIBRARY 66
ALKALOID/TERPENOID-INSPIRED COMPOUND COLLECTION 67
MACROCYCLIC COMPOUND COLLECTIONS 68
MACROSPHELIDE A-INSPIRED COMPOUND COLLECTION 68
SOLID-PHASE SYNTHESIS OF ANALOGS OF ERYTHROMYCIN A 69
AN ALDOL-BASED BUILD/COUPLE/PAIR STRATEGY FOR THE SYNTHESIS OF
MACROCYCLES AND MEDIUM-SIZED RINGS 71
OUDOOK 72
REFERENCES 73
FROM MARKETED DRUGS TO DESIGNED ANALOGS AND CLINICAL
CANDIDATES 81
CHEMISTRY AND BIOLOGY OF EPOTHILONES 83
KARI-HEINZ ALTMANN AND DIETER SCHINZER
INTRODUCTION: DISCOVERY AND BIOLOGICAL ACTIVITY 83
SYNTHESIS OF NATURAL EPOTHILONES 86
CONTENTS | VII
3.3 SYNTHESIS AND BIOLOGICAL ACTIVITY OF NON-NATURAL EPOTHILONES 90
3.3.1 SEMISYNTHETIC DERIVATIVES 90
3.3.2 FULLY SYNTHETIC ANALOGS 92
3.3.2.1 POLYKETIDE-BASED MACROCYCLES 92
3.3.2.2 AZA-EPOTHILONES (AZATHILONES) 109
3.3.2.3 HYBRID STRUCTURES AND ACYCLIC ANALOGS 112
3.4 CONFORMATIONAL STUDIES AND PHARMACOPHORE MODELING 114
3.5 CONCLUSIONS 115
REFERENCES 115
4 TAXOL, TAXOIDS, AND RELATED TAXANES 127
IWAO OJIMA, ANUSHREE KAMATH, AND JOSHUA D. SEITZ
4.1 INTRODUCTION AND HISTORICAL BACKGROUND 127
4.1.1 DISCOVERY OF TAXOL (PADITAXEL): AN EPOCH-MAKING ANTICANCER
DRUG FROM NATURE 127
4.1.2 TAXANE FAMILY 128
4.1.3 SOURCES AND METHODS OF PRODUCTION 129
4.1.3.1 EXTRACTION FROM YEW TREES 129
4.1.3.2 SEMISYNTHESIS 129
4.1.3.3 TOTAL SYNTHESIS 130
4.1.3.4 BIOTECHNOLOGY PROCESSES 131
4.1.4 CLINICAL DEVELOPMENT OF TAXOL (TAXOL) 131
4.2 MECHANISM OF ACTION AND DRUG RESISTANCE 132
4.2.1 TAXOL, CELL CYCLE ARREST, AND APOPTOSIS 132
4.2.2 DRUG RESISTANCE TO TAXOL 133
4.3 STRUCTURE-ACTIVITY RELATIONSHIPS (SAR) OF TAXOL 133
4.3.1 SAR OF TAXOL 133
4.3.2 CHEMICAL MODIFICATIONS OF TAXOL: TAXOL DERIVATIVES
AND TAXOIDS 134
4.3.2.1 MODIFICATIONS IN THE C13 SIDE CHAIN 134
4.3.2.2 MODIFICATION IN THE BACCATIN COMPONENT 135
4.3.2.3 PRODRUGS OFTAXOL 140
4.4 STRUCTURAL AND CHEMICAL BIOLOGY OFTAXOL 141
4.4.1 BIOACTIVE CONFORMATION OFTAXOL 141
4.4.2 MICROTUBULE-BINDING KINETICS OFTAXOL 145
4.5 NEW-GENERATION TAXOIDS FROM 10-DAB 145
4.5.1 TAXOIDS FROM 10-DAB 145
4.5.2 TAXOIDS FROM 14(3-HYDROXYBACCATIN III 148
4.5.3 TAXOIDS FROM 9-DIHYDROBACCATIN III 149
4.6 TAXOIDS IN CLINICAL DEVELOPMENT 150
4.6.1 DOCETAXEL (TAXOTERE, RP 56976) 150
4.6.2 CABAZITAXEL (JEVTANA, RPR 116258A, XRP6258) 153
4.6.3 LAROTAXEL (XRP9881, RPR109881) 153
4.6.4 ORTATAXEL (SB-T-101131, IDN5109, BAY59-8862,
ISN 5109) 154
VIII
| CONTENTS
4.6.5 TESETAXEL (DJ-927) 154 *
4.6.6 MILATAXEL (MAC-321, TL139) 155
4.7 NEW APPLICATIONS OF TAXANES 155
4.7.1 TAXANE-BASED MDR REVERSAL AGENTS 155
4.7.2 TAXANES AS ANTIANGIOGENIC AGENTS 156
4.7.3 TAXANES AS ANTITUBERCULAR AGENTS 157
4.8 CONCLUSIONS AND PERSPECTIVE 158
REFERENCES 159
5 CAMPTOTHECIN AND ANALOGS 181
GIUSEPPE
C
IANNINI
5.1 INTRODUCTION 181
5.2 BIOLOGY ACTIVITY 185
5.2.1 CAMPTOTHECIN ACTS ON EUKARYOTIC TOP 1 187
5.2.2 DRUG RESISTANCE AND TOPOISOMERASE MUTATION 189
5.2.3 CAMPTOTHECIN: BEYOND THE TOPOISOMERASE I 190
5.2.4 OFF-LABEL INVESTIGATION 190
5.3 CAMPTOTHECIN IN CLINICAL USE AND UNDER CLINICAL TRIALS 190
5.3.1 HOMOCAMPTOTHECIN 203
5.4 CHEMISTRY 204
5.4.1 TOTAL SYNTHESES 205
5.4.2 SYNTHESES OF SOME REPRESENTATIVE CAMPTOTHECIN DERIVATIVES 207
5.5 STRUCTURE-ACTIVITY RELATIONSHIP 210
5.6 XENOGRAFT STUDIES 211
5.7 PRODRUG/TARGETING 212
5.8 DEVELOPMENTS OF MODERN CHROMATOGRAPHIC METHODS APPLIED TO
CPT 214
5.9 CONCLUSIONS AND PERSPECTIVES 214
REFERENCES 215
6 A SHORT HISTORY OF THE DISCOVERY AND DEVELOPMENT OF NALTREXONE AND
OTHER MORPHINE DERIVATIVES 225
VIMAL VARGHESE AND TOMAS HUDLICKY
6.1 INTRODUCTION 225
6.2 HISTORY AND DEVELOPMENT 226
6.3 PHARMACOLOGY 238
6.4 STRUCTURE-ACTIVITY RELATIONSHIP OF MORPHINE AND ITS ANALOGS 240
6.5 CONCLUSIONS AND OUDOOK 244
REFERENCES 244
7 LINCOSAMIDE ANTIBACTERIALS 251
HARDWIN O DOWD, ALICE L. ERWIN, AND
JASON C. LEWIS
7.1 INTRODUCTION 251
7.2 MECHANISM OF ACTION 253
7.3 ANTIBACTERIAL SPECTRUM 254
CONTENTS IIX
7.4 RESISTANCE 257
7.5 PSEUDOMEMBRANOUS COLITIS 258
7.6 NEXT-GENERATION LINCOSAMIDES 259
7.7 CONCLUSIONS 264
REFERENCES 264
8 PLATENSIMYCIN AND PLATENCIN 271
ARUN K. GHOSH AND KAI XI
8.1 INTRODUCTION AND HISTORICAL BACKGROUND 271
8.2 DISCOVERY AND BIOACTIVITIES OF PLATENSIMYCIN AND PLATENCIN 272
8.3 TOTAL AND FORMAL SYNTHESES OF PLATENSIMYCIN 278
8.4 TOTAL AND FORMAL SYNTHESES OF PLATENCIN 283
8.5 ANALOGS OF PLATENSIMYCIN AND PLATENCIN 287
8.6 CONCLUSIONS AND PERSPECTIVE 295
REFERENCES 296
9 FROM NATURAL PRODUCT TO NEW DIABETES THERAPY: PHLORIZIN AND THE
DISCOVERY OF SGLT2 INHIBITOR CLINICAL CANDIDATES 301
VINCENT MASCITTI AND RALPH P. ROBINSON
9.1 INTRODUCTION 301
9.2 PHLORIZIN: A DRUG LEAD FROM APPLE TREES 302
9.3 PHLORIZIN: MECHANISM OF ACTION 304
9.4 PHLORIZIN, SGITS, AND DIABETES 306
9.5 PHLORIZIN ANALOGS: O-GLUCOSIDES 306
9.6 PHLORIZIN ANALOGS: C-GLUCOSIDES 309
9.7 C-GLUCOSIDES: AGLYCONE MODIFICATIONS 314
9.8 C-GLUCOSIDES: SUGAR MODIFICATIONS 316
9.9 CONCLUSIONS 325
REFERENCES 325
10 AERUGINOSINS AS THROMBIN INHIBITORS 333
JUAN R. DEL VALLE, ERIC THERRIEN, AND STEPHEN HANESSIAN
10.1 INTRODUCTION 333
10.2 TARGETING THE BLOOD COAGULATION CASCADE 333
10.3 STRUCTURE OF THROMBIN 335
10.4 THE AERUGINOSIN FAMILY 336
10.4.1 AERUGINOSIN 298A AND RELATED MICROCYSTIS SP. PEPTIDES 336
10.4.2 OSCILLARIN AND RELATED OSCILLATORIA SP. PEPTIDES 339
10.4.3 DYSINOSIN A AND RELATED PEPTIDES FROM DYSIDAEDAE SPONGES
10.4.4 STRUCTURALLY RELATED ANTITHROMBIN PEPTIDE NATURAL PRODUCTS
10.4.5 CLOSE ANALOGS OF ANTITHROMBOTIC AERUGINOSINS 344
10.5 MIMICKING NATURE 346
10.5.1 THE 50-YEAR CHALLENGE 348
10.5.2 PEPTIDE ANALOGS 350
10.5.3 PEPTIDOMIMETICS 352
340
342
X | CONTENTS
10.6 CONCLUSIONS 355
REFERENCES 356
PART THREE NATURAL PRODUCTS AS AN INCENTIVE FOR ENABLING TECHNOLOGIES
365
11 MACROLIDES AND ANTIFUNGALS VIA BIOTRANSFORMATION 367
AARON E. MAY AND CHAITAN KHOSLA
11.1 INTRODUCTION TO POLYKETIDES AND THEIR ACTIVITY 367
11.2 MECHANISM OF POLYKETIDE BIOSYNTHESIS 367
11.2.1 ERYTHROMYCIN 371
11.2.2 AVERMECTIN/DORAMECTIN 377
11.2.3 TETRACYCLINES 381
11.2.4 SALINOSPORAMIDES 385
11.3 CONCLUSIONS 391
REFERENCES 392
12 UNNATURAL NUCLEOSIDE ANALOGS FOR ANTISENSE THERAPY 403
PUNIT P. SETH AND ERIC E. SWAYZE
12.1 NATURE USES NUCLEIC ACID POLYMERS FOR STORAGE, TRANSFER, SYNTHESIS,
AND REGULATION OF GENETIC INFORMATION 403
12.2 THE ANTISENSE APPROACH TO DRUG DISCOVERY 404
12.3 THE MEDICINAL CHEMISTRY APPROACH TO OLIGONUCLEOTIDE
DRUGS 406
12.4 STRUCTURAL FEATURES OF DNA AND RNA DUPLEXES 407
12.5 IMPROVING BINDING AFFINITY OF OLIGONUCLEOTIDES BY STRUCTURAL
MIMICRY
OF RNA 410
12.5.1 2 -MODIFIED RNA 411
12.5.1.1 2 -0-ME RNA 411
12.5.1.2 2 -0-METHOXYETHYL RNA 412
12.5.1.3 2 -FLUORO RNA 413
12.5.2 2 ,4 -BRIDGED NUCLEIC ACIDS 414
12.5.2.1 2 ,4 -CONSTRAINED MOE AND 2 ,4 -CONSTRAINED ETHYL BNA 415
12.5.2.2 5 -ME-LNA 416
12.5.2.3 CARBOCYCLIC LNA ANALOGS 417
12.5.2.4 RING-EXPANDED BNA ANALOGS 417
12.5.2.5 A
-L
-BRIDGED NUCLEIC ACIDS 418
12.5.3 HEXITOL NUCLEIC ACIDS 420
12.6 IMPROVING BINDING AFFINITY OF OLIGONUCLEOTIDES BY CONFORMATIONAL
RESTRAINT OF DNA - THE BICYCLO- AND TRICYCLO-DNA CLASS OF NUCLEIC ACID
ANALOGS 421
12.7 IMPROVING BINDING AFFINITY OF OLIGONUCLEOTIDES BY CONFORMATIONAL
RESTRAINT OF THE PHOSPHODIESTER BACKBONE - A,(3-CONSTRAINED NUCLEIC
ACIDS 423
12.8 NATURALLY OCCURRING BACKBONE MODIFICATIONS 424
CONTENTS IXI
12.8.1 THE PHOSPHOROTHIOATE MODIFICATION 425
12.9 NATURALLY OCCURRING HETEROCYCLE MODIFICATIONS 426
12.9.1 5-SUBSTITUTED PYRIMIDINE ANALOGS 427
12.10 OUTLOOK 428
REFERENCES 429
13 HYBRID
NATURAL PRODUCTS 441
KEISUKE SUZUKI AND YOSHIZUMI YASUI
13.1 INTRODUCTION 441
13.2 STAUROSPORINES (AMINO ACID-SUGAR HYBRIDS) 444
13.2.1 OCCURRENCE 444
13.2.2 BIOACTIVITY 445
13.2.3 BIOSYNTHESIS 446
13.2.4 SYNTHESIS 446
13.2.5 MEDICINAL CHEMISTRY 447
13.3 LINCOMYCINS (AMINO ACID-SUGAR HYBRIDS) 448
13.3.1 OCCURRENCE 448
13.3.2 BIOACTIVITY 448
13.3.3 BIOSYNTHESIS 448
13.3.4 MEDICINAL CHEMISTRY 449
13.4 MADINDOLINES (AMINO ACID-POLYKETIDE HYBRIDS) 449
13.4.1 OCCURRENCE 449
13.4.2 BIOACTIVITY 450
13.4.3 SYNTHESIS 451
13.5 KAINOIDS (AMINO ACID-TERPENE HYBRIDS) 451
13.5.1 OCCURRENCE 451
13.5.2 BIOACTIVITY 451
13.5.3 BIOSYNTHESIS 453
13.5.4 SYNTHESIS 453
13.5.5 MEDICINAL CHEMISTRY 453
13.6 BENANOMICIN-PRADIMICIN ANTIBIOTICS (SUGAR-POLYKETIDE HYBRIDS) 455
13.6.1 OCCURRENCE 455
13.6.2 BIOACTIVITY 455
13.6.3 MEDICINAL CHEMISTRY 456
13.6.4 SYNTHESIS 457
13.7 ANGUCYDINES (SUGAR-POLYKETIDE HYBRIDS) 457
13.7.1 OCCURRENCE AND BIOSYNTHESIS 457
13.7.2 BIOACTIVITY 459
13.7.3 SYNTHESIS 460
13.8 FURAQUINOCINS (POLYKETIDE-TERPENE HYBRIDS) 462
13.8.1 OCCURRENCE 462
13.8.2 BIOSYNTHESIS 464
13.8.3 SYNTHESIS 464
13.9 CONCLUSIONS 467
REFERENCES 467
XII
| CONTENTS
PART FOUR
NATURAL PRODUCTS AS PHARMACOLOGICAL TOOLS 473
14 RETHINKING THE ROLE
OF NATURAL PRODUCTS: FUNCTION-ORIENTED SYNTHESIS,
BRYOSTATIN, AND BRYOLOGS 475
PAUL A. WENDER, ALISON C. DONNELLY, BRIAN A LOY,
KATHERINE E. NEAR, AND
DARYL STATENESS
14.1 INTRODUCTION 475
14.2 INTRODUCTION TO FUNCTION-ORIENTED SYNTHESIS 476
14.2.1 REPRESENTATIVE EXAMPLES OF FUNCTION-ORIENTED SYNTHESIS 478
14.3 INTRODUCTION TO BRYOSTATIN 489
14.4 BRYOSTATIN TOTAL SYNTHESES 493
14.4.1 TOTAL SYNTHESES OF BRYOSTATINS 2, 3, AND 7 (1990-2000) 493
14.4.2 TOTAL SYNTHESIS OF BRYOSTATIN 16 (2008) 494
14.4.3 TOTAL SYNTHESIS OF BRYOSTATIN 1 (2011) 495
14.4.4 TOTAL SYNTHESIS OF BRYOSTATIN 9 (2011) 495
14.4.5 TOTAL SYNTHESIS OF BRYOSTATIN 7 (2011) 495
14.5 APPLICATION OF FOS TO THE BRYOSTATIN SCAFFOLD 496
14.5.1 INITIAL PHARMACOPHORIC INVESTIGATIONS ON THE BRYOSTATIN SCAFFOLD
498
14.5.2 DESIGN OF THE FIRST SYNTHETICALLY ACCESSIBLE FUNCTIONAL
BRYOSTATIN
ANALOGS 500
14.5.3 INITIAL PRECLINICAL INVESTIGATIONS OF FUNCTIONAL BRYOSTATIN
ANALOGS 508
14.5.4 DES-A-RING ANALOGS 510
14.5.5 C13-FUNCTIONALIZED ANALOGS 514
14.5.6 B-RING DIOXOLANE ANALOG 516
14.5.7 C20 ANALOGS 518
14.5.8 C7 ANALOGS 520
14.5.9 A-RING FUNCTIONALIZED BRYOSTATIN ANALOGS 522
14.5.10 NEW METHODOLOGY. PRINS-DRIVEN MACROCYCLIZATION TOWARD B-RING
PYRAN
ANALOGS 527
14.5.11 A-RING FUNCTIONALIZED ANALOGS AND INDUCTION OF LATENT HIV
EXPRESSION 529
14.6 CONCLUSIONS 533
REFERENCES 533
15 CYDOPAMINE AND CONGENERS 545
PHILIPP HERETSCH AND ATHANASSIOS CIANNIS
15.1 INTRODUCTION 545
15.2 THE DISCOVERY OF CYDOPAMINE 545
15.3 ACCESSIBILITY OF CYDOPAMINE 547
15.4 THE HEDGEHOG SIGNALING PATHWAY 549
15.5 MEDICAL RELEVANCE OF CYDOPAMINE AND THE HEDGEHOG SIGNALING
PATHWAY 551
15.5.1 MODELS OF CANCER INVOLVING THE HEDGEHOG SIGNALING PATHWAY 551
15.5.2 HEDGEHOG SIGNALING PATHWAY INHIBITORS FOR THE TREATMENT OF
PANCREATIC
CANCER, MYELOFIBROSIS, AND CHONDROSARCOMA 552
15.5.3
15.6
15.7
PART FIVE
16
16.1
16.2
16.3
16.3.1
16.3.2
16.3.3
16.4
16.4.1
16.4.2
16.5
16.6
16.6.1
16.6.2
16.7
16.8
16.8.1
16.8.2
16.8.3
16.9
16.10
16.11
16.12
16.13
CONTENTS | XIII
PRODRUGS OF CYCLOPAMINE 555
FURTHER MODULATORS OF THE HEDGEHOG SIGNALING PATHWAY 556
SUMMARY AND OUTLOOK 558
REFERENCES 558
NATURE:
THE PROVIDER, THE ENTICER, AND THE HEATER 565
HYBRIDS, CONGENERS, MIMICS, AND CONSTRAINED VARIANTS SPANNING 30
YEARS OF NATURAL PRODUCTS CHEMISTRY: A PERSONAL RETROSPECTIVE 567
STEPHEN HANESSIAN
INTRODUCTION 567
STRUCTURE-BASED ORGANIC SYNTHESIS 570
NUCLEOSIDES 572
QUANTAMYCIN 572
MALAYAMYCIN A 573
HYDANTOCIDIN 573
(3-LACTAMS 576
ANALOG DESIGN 576
UNNATURAL (S-LACTAMS 577
MORPHINOMIMETICS 579
HISTONE DEACETYLASE INHIBITORS 580
ACYCLIC INHIBITORS 581
MACROCYCLIC INHIBITORS 582
PACTAMYCIN ANALOGS 583
AERUGINOSAS: FROM NATURAL PRODUCTS TO ACHIRAL ANALOGS 586
STRUCTURE-BASED HYBRIDS AND TRUNCATED ANALOGS 586
CONSTRAINED PEPTIDOMIMETICS 589
ACHIRAL INHIBITORS 589
AVERMECTIN BI
A
AND BAFILOMYCIN AJ 591
BAFILOMYCIN A! 592
3-N,N-DIMETHYLAMINO IINCOMYCIN 594
OXAZOLIDINONE KETOLIDE MIMETICS 595
EPILOGUE 596
REFERENCES 598
INDEX 611
|
| any_adam_object | 1 |
| author2 | Hanessian, Stephen |
| author2_role | edt |
| author2_variant | s h sh |
| author_GND | (DE-588)172124506 |
| author_facet | Hanessian, Stephen |
| building | Verbundindex |
| bvnumber | BV041736008 |
| classification_rvk | VK 8500 VS 5350 |
| ctrlnum | (OCoLC)877909638 (DE-599)BVBBV041736008 |
| discipline | Chemie / Pharmazie |
| format | Book |
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| id | DE-604.BV041736008 |
| illustrated | Illustrated |
| indexdate | 2024-07-10T01:04:06Z |
| institution | BVB |
| isbn | 9783527332182 9783527676545 |
| language | English |
| oai_aleph_id | oai:aleph.bib-bvb.de:BVB01-027182706 |
| oclc_num | 877909638 |
| open_access_boolean | |
| owner | DE-29 DE-188 DE-19 DE-BY-UBM DE-11 DE-20 DE-355 DE-BY-UBR |
| owner_facet | DE-29 DE-188 DE-19 DE-BY-UBM DE-11 DE-20 DE-355 DE-BY-UBR |
| physical | XXI, 630 S. Ill., graph. Darst. |
| publishDate | 2014 |
| publishDateSearch | 2014 |
| publishDateSort | 2014 |
| publisher | Wiley-VCH |
| record_format | marc |
| series | Methods and principles in medicinal chemistry |
| series2 | Methods and principles in medicinal chemistry |
| spelling | Natural products in medicinal chemistry ed. by Stephen Hanessian Weinheim Wiley-VCH 2014 XXI, 630 S. Ill., graph. Darst. txt rdacontent n rdamedia nc rdacarrier Methods and principles in medicinal chemistry 60 Includes bibliographical references and index Natural products Organic compounds / Synthesis Pharmaceutical chemistry Organische Chemie (DE-588)4043793-0 gnd rswk-swf Bio-Produkt (DE-588)4345488-4 gnd rswk-swf Pharmazeutische Biologie (DE-588)4045693-6 gnd rswk-swf Pharmazeutische Biologie (DE-588)4045693-6 s Bio-Produkt (DE-588)4345488-4 s Organische Chemie (DE-588)4043793-0 s DE-188 Hanessian, Stephen (DE-588)172124506 edt Erscheint auch als Online-Ausgabe, EPUB 978-3-527-67656-9 Erscheint auch als Online-Ausgabe, MOBI 978-3-527-67657-6 Erscheint auch als Online-Ausgabe, PDF 978-3-527-67655-2 Methods and principles in medicinal chemistry 60 (DE-604)BV035418617 60 DNB Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=027182706&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Natural products in medicinal chemistry Methods and principles in medicinal chemistry Natural products Organic compounds / Synthesis Pharmaceutical chemistry Organische Chemie (DE-588)4043793-0 gnd Bio-Produkt (DE-588)4345488-4 gnd Pharmazeutische Biologie (DE-588)4045693-6 gnd |
| subject_GND | (DE-588)4043793-0 (DE-588)4345488-4 (DE-588)4045693-6 |
| title | Natural products in medicinal chemistry |
| title_auth | Natural products in medicinal chemistry |
| title_exact_search | Natural products in medicinal chemistry |
| title_full | Natural products in medicinal chemistry ed. by Stephen Hanessian |
| title_fullStr | Natural products in medicinal chemistry ed. by Stephen Hanessian |
| title_full_unstemmed | Natural products in medicinal chemistry ed. by Stephen Hanessian |
| title_short | Natural products in medicinal chemistry |
| title_sort | natural products in medicinal chemistry |
| topic | Natural products Organic compounds / Synthesis Pharmaceutical chemistry Organische Chemie (DE-588)4043793-0 gnd Bio-Produkt (DE-588)4345488-4 gnd Pharmazeutische Biologie (DE-588)4045693-6 gnd |
| topic_facet | Natural products Organic compounds / Synthesis Pharmaceutical chemistry Organische Chemie Bio-Produkt Pharmazeutische Biologie |
| url | http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=027182706&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
| volume_link | (DE-604)BV035418617 |
| work_keys_str_mv | AT hanessianstephen naturalproductsinmedicinalchemistry |