Medicinal chemistry of bioactive natural products:
Gespeichert in:
| Format: | Buch |
|---|---|
| Sprache: | English |
| Veröffentlicht: |
Hoboken, NJ
Wiley
2006
|
| Schlagworte: | |
| Online-Zugang: | Table of contents Contributor biographical information Publisher description Inhaltsverzeichnis |
| Beschreibung: | Includes index. |
| Beschreibung: | XIX, 460 S. Ill., graph. Darst. |
| ISBN: | 9780471660071 0471660078 |
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| 300 | |a XIX, 460 S. |b Ill., graph. Darst. | ||
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| 650 | 4 | |a Pharmaceutical chemistry | |
| 650 | 4 | |a Natural products | |
| 650 | 4 | |a Bioactive compounds | |
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Datensatz im Suchindex
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| adam_text | CONTENTS
Preface xiii
Contributors xvii
1 The Chemistry and Biology of Epothilones—Lead Structures
for the Discovery of Improved Microtubule Inhibitors 1
Karl Heinz Altmann
1.1. Introduction 1
1.2. Biological Effects of Epo B 4
1.2.1 In Vitro Activity 4
1.2.2 In Vivo Antitumor Activity 8
1.3. Epothilone Analogs and SAR Studies 9
1.3.1 Lactam Based Analogs 9
1.3.2 Modifications in the C9 C11 Region 10
1.3.3 Modifications of the Epoxide Moiety 13
1.3.4 C 26 Modified Analogs 17
1.3.5 Side Chain Modifications 18
1.3.6 Aza Epothilones 22
1.4. Pharmacophore Modeling and Conformational Studies 25
1.5. Epothilone Analogs in Clinical Development 26
1.6. Conclusions 28
Acknowledgments 29
References 29
vlil CONTENTS
4.7.2 Structure Based HA Analog Design 167
4.8. ZT 1: New Generation of HA AChE 169
4.8.1 Pharmacology 170
4.8.2 Toxicology 170
4.8.3 Pharmacokinetics 171
4.8.4 Clinical Trials 172
Abbreviations 172
References 173
5 Qinghaosu (Artemisinin)—A Fantastic Antimalarial
Drug from a Traditional Chinese Medicine 183
Ying Li, Hao Huang, and Yu Lin Wu
5.1. Introduction 183
5.2. Qinghaosu and Qinghao (Artemisia annua L. Composites) 184
5.2.1. Discovery and Structure Determination of Qinghaosu 184
5.2.2. The Phytochemistry of Qinghao and Other Natural
Products from Qinghao 188
5.3. Reaction of Qinghaosu 197
5.3.1. Reduction of Qinghaosu 198
5.3.2. Acidic Degradation of Qinghaosu 199
5.3.3. Miscellaneous Chemical Reaction 201
5.3.4. Biotransformation 201
5.4. Chemical Synthesis and Biosynthesis of Qinghaosu 202
5.4.1. Partial Synthesis and Total Synthesis of Qinghaosu 202
5.4.2. Biogenetic Synthesis of Qinghaosu 204
5.5. Derivatives and Antimalarial Activity 206
5.5.1 Modification on C 12 of Qinghaosu 207
5.5.2 Water Soluble Qinghaosu Derivatives 212
5.5.3 Modification on C 11 or/and C 12 215
5.5.4 Modification on C 4 or/and C 12 215
5.5.5 Modification on C 3 or/and C 13 216
5.5.6 Modification on C 13 216
5.5.7 Modification on C 11 and C 12 217
5.5.8 Azaartemisinin 217
5.5.9 Carbaartemisinin 218
5.5.10 Steroidal Qinghaosu Derivatives 218
5.5.11 Dimers and Trimers 219
5.5.12 1,2,4 Trioxanes and 1,2,4,5 Tetraoxanes 221
CONTENTS ix
5.6. Pharmacology and Chemical Biology of Qinghaosu
and Its Derivatives 221
5.6.1 Bioactivities of Qinghaosu Derivatives and Analogs 221
5.6.2 Early Biologically Morphologic Observation of the
Antimalarial Action of Qinghaosu 224
5.6.3 The Free Radical Reaction of Qinghaosu and Its
Derivatives With Fe(II) 225
5.6.4 Antimalarial Activity and the Free Radical Reaction
of Qinghaosu and Its Derivatives 230
5.6.5 Interaction of Biomolecules with Carbon Centered
Free Radical 235
5.6.6 Another Point of View and Summary 238
5.7 Conclusion 239
References 239
6 Progress of Studies on the Natural Cembranoids
from the Soft Coral Species of Sarcophyton Genus 257
Yulin Li, Lizeng Peng, and Tao Zhang
6.1. Introduction 257
6.2. Cembrane Type Constituents from the Sarcophyton Genus 258
6.2.1 Sarcophytols from the Sarcophyton Genus 258
6.2.2 The Other Cembrane Type Constituents
from the Sarcophyton Genus 260
6.3. Physiological Action of Sarcophytol A and Sarcophytol B 265
6.4. Total Synthesis of the Natural Cembranoids 266
6.4.1 Total Synthesis of Sarcophytols 267
6.4.2 Total Synthesis of Cembrene A and C 271
6.4.3 Total Synthesis of Several Natural Epoxy Cembrenoids 277
6.4.4 Total Synthesis of Cembranolides 287
6.5. Studies on Novel Macrocyclization Methods of
Cembrane Type Diterpenoids 291
6.5.1 A Stille Cyclization Approach to (±) Isocembrene 291
Acknowledgments 296
References 296
7 Medicinal Chemistry of Ginkgolides from Ginkgo biloba 301
Kristian Str0mgaard
7.1. Introduction 301
7.1.1 Ginkgo biloba Extract 301
x CONTENTS
7.1.2 Isolation and Structure Elucidation of Ginkgolides 304
7.1.3 Biosynthesis of Ginkgolides 306
7.1.4 Chemistry of Ginkgolides 307
7.2. Ginkgolides and the PAF Receptor 308
7.3. Ginkgolides and Glycine Receptors 312
7.4. Various Effects of Ginkgolides 314
7.5. Conclusions and Outlook 315
Acknowledgment 315
References 315
8 Recent Progress in Calophyllum Coumarins as
Potent Anti HIV Agents 325
Lin Wang, Tao Ma, and Gang Liu
8.1. Introduction 325
8.2. Anti HIV 1 Activity of Calophyllum Coumarins 329
8.2.1 Anti HIV 1 Activity of Calanolides 329
8.2.2 Anti HIV 1 Activity of InophyHums 331
8.2.3 Anti HIV 1 Activity of Cordatolides 333
8.3. Pharmacology of Calanolides 333
8.3.1 Pharmacology of (+) Calanolide A 333
8.3.2 Clinical Trial of (+) Calanolide A 334
8.4. Preparation of Calophyllum Coumarins 334
8.4.1 Total Synthesis of Racemic Calophyllum Coumarins 334
8.4.2 Preparation of Optically Active Calophyllum Coumarins 340
8.5. Structure Modification of Calanolides 349
8.6. Conclusion 350
References 351
9 Recent Progress and Prospects on Plant Derived
Anti HIV Agents and Analogs 357
Donglei Yu and Kuo Hsiung Lee
9.1. Introduction 357
9.2. Khellactone Coumarin Analogs as Anti HIV Agents 358
9.2.1 Suksdorfin as a New Anti HIV Agent 358
9.2.2 Pyrano 3 ,4 Stereoselectivity and Modification 359
9.2.3 Coumarin Skeleton Modification 362
9.2.4 SAR Conclusions 373
9.2.5 Mechanism of Action 374
CONTENTS xi
9.3. Biphenyl Derivatives as Anti HIV Agents 374
9.3.1 SAR Analysis of Naturally Occurring
Dibenzocyclooctadiene Lignans 374
9.3.2 Structural Modifications 376
9.3.3 SAR Conclusions 378
9.3.4 Mechanism of Action of Biphenyl Derivatives 378
9.4. Triterpene Betulinic Acid Derivatives as Anti HIV Agents 379
9.4.1 Betulinic Acid Derivatives as Entry Inhibitors 379
9.4.2 Betulinic Acid Derivatives as Maturation Inhibitors 386
9.4.3 Bifunctional Betulinic Acid Derivatives with Dual
Mechanisms of Action 389
9.5. Conclusions 391
Acknowledgments 391
References 391
10 Recent Progress on the Chemical Synthesis of Annonaceous
Acetogenins and Their Structurally Modified Mimics 399
Tai Shan Hu, Yu Lin Wu, and Zhu Jun Yao
10.1. Introduction 399
10.2. Total Synthesis of Mono THF Acetogenins 401
10.3. Total Synthesis of Bis THF Acetogenins 413
10.4. Total Synthesis of THP Containing Acetogenins 422
10.5. Design and Synthesis of Mimics of Acetogenins 428
10.6. Summary 437
References 437
Index 443
|
| adam_txt |
CONTENTS
Preface xiii
Contributors xvii
1 The Chemistry and Biology of Epothilones—Lead Structures
for the Discovery of Improved Microtubule Inhibitors 1
Karl Heinz Altmann
1.1. Introduction 1
1.2. Biological Effects of Epo B 4
1.2.1 In Vitro Activity 4
1.2.2 In Vivo Antitumor Activity 8
1.3. Epothilone Analogs and SAR Studies 9
1.3.1 Lactam Based Analogs 9
1.3.2 Modifications in the C9 C11 Region 10
1.3.3 Modifications of the Epoxide Moiety 13
1.3.4 C 26 Modified Analogs 17
1.3.5 Side Chain Modifications 18
1.3.6 Aza Epothilones 22
1.4. Pharmacophore Modeling and Conformational Studies 25
1.5. Epothilone Analogs in Clinical Development 26
1.6. Conclusions 28
Acknowledgments 29
References 29
vlil CONTENTS
4.7.2 Structure Based HA Analog Design 167
4.8. ZT 1: New Generation of HA AChE 169
4.8.1 Pharmacology 170
4.8.2 Toxicology 170
4.8.3 Pharmacokinetics 171
4.8.4 Clinical Trials 172
Abbreviations 172
References 173
5 Qinghaosu (Artemisinin)—A Fantastic Antimalarial
Drug from a Traditional Chinese Medicine 183
Ying Li, Hao Huang, and Yu Lin Wu
5.1. Introduction 183
5.2. Qinghaosu and Qinghao (Artemisia annua L. Composites) 184
5.2.1. Discovery and Structure Determination of Qinghaosu 184
5.2.2. The Phytochemistry of Qinghao and Other Natural
Products from Qinghao 188
5.3. Reaction of Qinghaosu 197
5.3.1. Reduction of Qinghaosu 198
5.3.2. Acidic Degradation of Qinghaosu 199
5.3.3. Miscellaneous Chemical Reaction 201
5.3.4. Biotransformation 201
5.4. Chemical Synthesis and Biosynthesis of Qinghaosu 202
5.4.1. Partial Synthesis and Total Synthesis of Qinghaosu 202
5.4.2. Biogenetic Synthesis of Qinghaosu 204
5.5. Derivatives and Antimalarial Activity 206
5.5.1 Modification on C 12 of Qinghaosu 207
5.5.2 Water Soluble Qinghaosu Derivatives 212
5.5.3 Modification on C 11 or/and C 12 215
5.5.4 Modification on C 4 or/and C 12 215
5.5.5 Modification on C 3 or/and C 13 216
5.5.6 Modification on C 13 216
5.5.7 Modification on C 11 and C 12 217
5.5.8 Azaartemisinin 217
5.5.9 Carbaartemisinin 218
5.5.10 Steroidal Qinghaosu Derivatives 218
5.5.11 Dimers and Trimers 219
5.5.12 1,2,4 Trioxanes and 1,2,4,5 Tetraoxanes 221
CONTENTS ix
5.6. Pharmacology and Chemical Biology of Qinghaosu
and Its Derivatives 221
5.6.1 Bioactivities of Qinghaosu Derivatives and Analogs 221
5.6.2 Early Biologically Morphologic Observation of the
Antimalarial Action of Qinghaosu 224
5.6.3 The Free Radical Reaction of Qinghaosu and Its
Derivatives With Fe(II) 225
5.6.4 Antimalarial Activity and the Free Radical Reaction
of Qinghaosu and Its Derivatives 230
5.6.5 Interaction of Biomolecules with Carbon Centered
Free Radical 235
5.6.6 Another Point of View and Summary 238
5.7 Conclusion 239
References 239
6 Progress of Studies on the Natural Cembranoids
from the Soft Coral Species of Sarcophyton Genus 257
Yulin Li, Lizeng Peng, and Tao Zhang
6.1. Introduction 257
6.2. Cembrane Type Constituents from the Sarcophyton Genus 258
6.2.1 Sarcophytols from the Sarcophyton Genus 258
6.2.2 The Other Cembrane Type Constituents
from the Sarcophyton Genus 260
6.3. Physiological Action of Sarcophytol A and Sarcophytol B 265
6.4. Total Synthesis of the Natural Cembranoids 266
6.4.1 Total Synthesis of Sarcophytols 267
6.4.2 Total Synthesis of Cembrene A and C 271
6.4.3 Total Synthesis of Several Natural Epoxy Cembrenoids 277
6.4.4 Total Synthesis of Cembranolides 287
6.5. Studies on Novel Macrocyclization Methods of
Cembrane Type Diterpenoids 291
6.5.1 A Stille Cyclization Approach to (±) Isocembrene 291
Acknowledgments 296
References 296
7 Medicinal Chemistry of Ginkgolides from Ginkgo biloba 301
Kristian Str0mgaard
7.1. Introduction 301
7.1.1 Ginkgo biloba Extract 301
x CONTENTS
7.1.2 Isolation and Structure Elucidation of Ginkgolides 304
7.1.3 Biosynthesis of Ginkgolides 306
7.1.4 Chemistry of Ginkgolides 307
7.2. Ginkgolides and the PAF Receptor 308
7.3. Ginkgolides and Glycine Receptors 312
7.4. Various Effects of Ginkgolides 314
7.5. Conclusions and Outlook 315
Acknowledgment 315
References 315
8 Recent Progress in Calophyllum Coumarins as
Potent Anti HIV Agents 325
Lin Wang, Tao Ma, and Gang Liu
8.1. Introduction 325
8.2. Anti HIV 1 Activity of Calophyllum Coumarins 329
8.2.1 Anti HIV 1 Activity of Calanolides 329
8.2.2 Anti HIV 1 Activity of InophyHums 331
8.2.3 Anti HIV 1 Activity of Cordatolides 333
8.3. Pharmacology of Calanolides 333
8.3.1 Pharmacology of (+) Calanolide A 333
8.3.2 Clinical Trial of (+) Calanolide A 334
8.4. Preparation of Calophyllum Coumarins 334
8.4.1 Total Synthesis of Racemic Calophyllum Coumarins 334
8.4.2 Preparation of Optically Active Calophyllum Coumarins 340
8.5. Structure Modification of Calanolides 349
8.6. Conclusion 350
References 351
9 Recent Progress and Prospects on Plant Derived
Anti HIV Agents and Analogs 357
Donglei Yu and Kuo Hsiung Lee
9.1. Introduction 357
9.2. Khellactone Coumarin Analogs as Anti HIV Agents 358
9.2.1 Suksdorfin as a New Anti HIV Agent 358
9.2.2 Pyrano 3',4' Stereoselectivity and Modification 359
9.2.3 Coumarin Skeleton Modification 362
9.2.4 SAR Conclusions 373
9.2.5 Mechanism of Action 374
CONTENTS xi
9.3. Biphenyl Derivatives as Anti HIV Agents 374
9.3.1 SAR Analysis of Naturally Occurring
Dibenzocyclooctadiene Lignans 374
9.3.2 Structural Modifications 376
9.3.3 SAR Conclusions 378
9.3.4 Mechanism of Action of Biphenyl Derivatives 378
9.4. Triterpene Betulinic Acid Derivatives as Anti HIV Agents 379
9.4.1 Betulinic Acid Derivatives as Entry Inhibitors 379
9.4.2 Betulinic Acid Derivatives as Maturation Inhibitors 386
9.4.3 Bifunctional Betulinic Acid Derivatives with Dual
Mechanisms of Action 389
9.5. Conclusions 391
Acknowledgments 391
References 391
10 Recent Progress on the Chemical Synthesis of Annonaceous
Acetogenins and Their Structurally Modified Mimics 399
Tai Shan Hu, Yu Lin Wu, and Zhu Jun Yao
10.1. Introduction 399
10.2. Total Synthesis of Mono THF Acetogenins 401
10.3. Total Synthesis of Bis THF Acetogenins 413
10.4. Total Synthesis of THP Containing Acetogenins 422
10.5. Design and Synthesis of Mimics of Acetogenins 428
10.6. Summary 437
References 437
Index 443 |
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| id | DE-604.BV021559838 |
| illustrated | Illustrated |
| index_date | 2024-07-02T14:34:25Z |
| indexdate | 2024-07-09T20:38:38Z |
| institution | BVB |
| isbn | 9780471660071 0471660078 |
| language | English |
| lccn | 2006000882 |
| oai_aleph_id | oai:aleph.bib-bvb.de:BVB01-014775800 |
| oclc_num | 63125814 |
| open_access_boolean | |
| owner | DE-19 DE-BY-UBM DE-91G DE-BY-TUM DE-29T |
| owner_facet | DE-19 DE-BY-UBM DE-91G DE-BY-TUM DE-29T |
| physical | XIX, 460 S. Ill., graph. Darst. |
| publishDate | 2006 |
| publishDateSearch | 2006 |
| publishDateSort | 2006 |
| publisher | Wiley |
| record_format | marc |
| spelling | Medicinal chemistry of bioactive natural products ed. by Xiao-Tian Liang ... Hoboken, NJ Wiley 2006 XIX, 460 S. Ill., graph. Darst. txt rdacontent n rdamedia nc rdacarrier Includes index. Química farmacêutica larpcal Materia medica, Vegetable Pharmaceutical chemistry Natural products Bioactive compounds Naturstoff (DE-588)4041418-8 gnd rswk-swf Pharmazeutische Chemie (DE-588)4132158-3 gnd rswk-swf Bioaktive Verbindungen (DE-588)4145589-7 gnd rswk-swf Naturstoff (DE-588)4041418-8 s Bioaktive Verbindungen (DE-588)4145589-7 s Pharmazeutische Chemie (DE-588)4132158-3 s DE-604 Liang, Xiao-Tian Sonstige oth http://www.loc.gov/catdir/toc/ecip066/2006000882.html Table of contents http://www.loc.gov/catdir/enhancements/fy0629/2006000882-b.html Contributor biographical information http://www.loc.gov/catdir/enhancements/fy0629/2006000882-d.html Publisher description HBZ Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=014775800&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Medicinal chemistry of bioactive natural products Química farmacêutica larpcal Materia medica, Vegetable Pharmaceutical chemistry Natural products Bioactive compounds Naturstoff (DE-588)4041418-8 gnd Pharmazeutische Chemie (DE-588)4132158-3 gnd Bioaktive Verbindungen (DE-588)4145589-7 gnd |
| subject_GND | (DE-588)4041418-8 (DE-588)4132158-3 (DE-588)4145589-7 |
| title | Medicinal chemistry of bioactive natural products |
| title_auth | Medicinal chemistry of bioactive natural products |
| title_exact_search | Medicinal chemistry of bioactive natural products |
| title_exact_search_txtP | Medicinal chemistry of bioactive natural products |
| title_full | Medicinal chemistry of bioactive natural products ed. by Xiao-Tian Liang ... |
| title_fullStr | Medicinal chemistry of bioactive natural products ed. by Xiao-Tian Liang ... |
| title_full_unstemmed | Medicinal chemistry of bioactive natural products ed. by Xiao-Tian Liang ... |
| title_short | Medicinal chemistry of bioactive natural products |
| title_sort | medicinal chemistry of bioactive natural products |
| topic | Química farmacêutica larpcal Materia medica, Vegetable Pharmaceutical chemistry Natural products Bioactive compounds Naturstoff (DE-588)4041418-8 gnd Pharmazeutische Chemie (DE-588)4132158-3 gnd Bioaktive Verbindungen (DE-588)4145589-7 gnd |
| topic_facet | Química farmacêutica Materia medica, Vegetable Pharmaceutical chemistry Natural products Bioactive compounds Naturstoff Pharmazeutische Chemie Bioaktive Verbindungen |
| url | http://www.loc.gov/catdir/toc/ecip066/2006000882.html http://www.loc.gov/catdir/enhancements/fy0629/2006000882-b.html http://www.loc.gov/catdir/enhancements/fy0629/2006000882-d.html http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=014775800&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
| work_keys_str_mv | AT liangxiaotian medicinalchemistryofbioactivenaturalproducts |