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Medicinal Chemistry of Bioactive Natural Products

Medicinal Chemistry of Bioactive Natural Products

Xiao-Tian Liang (Editor), Wei-Shuo Fang (Editor)

ISBN: 978-0-471-73934-0

Mar 2006

336 pages

Description

Current discoveries and research into bioactive natural products

Medicinal Chemistry of Bioactive Natural Products provides a much-needed survey of bioactive natural products and their applications in medicinal chemistry. This comprehensive reference features articles by some of the world's leading scientists in the field on discovery, structure elucidation, and elegant synthetic strategies--developed for natural products--with an emphasis on the structure activity relationship of bioactive natural products. The topics have been carefully chosen on the basis of relevance to current research and to importance as clinicially useful agents.

Rather than attempting to be a comprehensive encyclopedia of bioactive natural products, Medicinal Chemistry of Bioactive Natural Products guides the reader to the key developments in the field. By providing not only practical detail but a historical perspective on the chemistry and biology of the compounds under consideration, the book serves as a handy resource for researchers in their own work developing pharmaceuticals, and as an inspiring introduction for young scientists to the dynamic field of bioactive natural products research.

Enhanced by examples with updated research results, the discussion covers such topics as:
* The chemistry and biology of epothilones
* Vancomycin and other glycopeptide antibiotic derivates
* Antitumor and other related activities of Taxol and its analogs
* The antimalarial properties of the traditional Chinese medicine, Quinghaosu (artemisinin)
* Huperzine A: A natural drug for the treatment of Alzheimer's disease
* The medicinal chemistry of ginkgolides from Ginkgo biloba
* Recent progress in Calophyllum coumarins as potent anti-HIV agents
* Plant-derived anti-HIV agents and analogs
* Chemical synthesis of annonaceous acetogenins and their structurally modified mimics
Preface.

Contributors.

1 The Chemistry and Biology of Epothilones—Lead Structures for the Discovery of Improved Microtubule Inhibitors (Karl-Heinz Altmann).

1.1. Introduction.

1.2. Biological Effects of Epo B.

1.3. Epothilone Analogs and SAR Studies.

1.4. Pharmacophore Modeling and Conformational Studies.

1.5. Epothilone Analogs in Clinical Development.

1.6. Conclusions.

Acknowledgments.

References.

2 The Chemistry and Biology of Vancomycin and Other Glycopeptide Antibiotic Derivatives (Roderich D. Su¨ssmuth).

2.1. Introduction.

2.2. Classification of Glycopeptide Antibiotics.

2.3. Mode of Action.

2.4. Glycopeptide Resistance.

2.5. Biosynthesis.

2.6. Total Synthesis.

2.7. Glycopeptides as Chiral Selectors in Chromatography and Capillary Electrophoresis.

2.8. Structural Modifications of Glycopeptide Antibiotics and Structure Activity Relationship (SAR) Studies.

Acknowledgment.

References.

3 Structure Modifications and Their Influences on Antitumor and Other Related Activities of Taxol and Its Analogs (Wei-Shuo Fang, Qi-Cheng Fang, and Xiao-Tian Liang).

3.1. Discovery and Research and Development of Taxol.

3.2. Paclitaxel Analogs Active Against Normal Tumor Cells.

3.3. Exploration on Mechanism of Paclitaxel Related to Tubulin Binding and Quest for Its Pharmacophore.

3.4. Natural and Semisynthetic Taxoids Overcoming Multidrug Resistance (MDR).

3.5 Design, Synthesis and Pharmacological Activity of Prodrugs of Paclitaxel.

3.6 Other Biological Actions of Paclitaxel.

3.7 New Antimicrotubule Molecules Mimicking Action of Paclitaxel.

3.8 Conclusion.

Acknowledgments.

References.

4 The Overview of Studies on Huperzine A: A Natural Drug for the Treatment of Alzheimers Disease (Da-Yuan Zhu, Chang-Heng Tan, and Yi-Ming Li).

4.1 Introduction.

4.2. Profiles of HA.

4.3. Plant Resources.

4.4. Pharmacology.

4.5. Clinical Trials.

4.6. Synthesis of HA and Its Analogs.

4.7. Structural Biology.

4.8. ZT-1: New Generation of HA AChE.

Abbreviations.

References.

5 Qinghaosu (Artemisinin)A Fantastic Antimalarial Drug from a Traditional Chinese Medicine (Ying Li, Hao Huang, and Yu-Lin Wu).

5.1. Introduction.

5.2. Qinghaosu and Qinghao (Artemisia annua L. Composites).

5.3. Reaction of Qinghaosu.

5.4. Chemical Synthesis and Biosynthesis of Qinghaosu.

5.5. Derivatives and Antimalarial Activity.

5.6. Pharmacology and Chemical Biology of Qinghaosu and Its Derivatives.

5.7 Conclusion.

References.

6 Progress of Studies on the Natural Cembranoids from the Soft Coral Species of Sarcophyton Genus (Yulin Li, Lizeng Peng, and Tao Zhang).

6.1. Introduction.

6.2. Cembrane-Type Constituents from the Sarcophyton Genus.

6.3. Physiological Action of Sarcophytol A and Sarcophytol B.

6.4. Total Synthesis of the Natural Cembranoids.

6.5. Studies on Novel Macrocyclization Methods of Cembrane-Type Diterpenoids.

Acknowledgments.

References.

7 Medicinal Chemistry of Ginkgolides from Ginkgo biloba (Kristian Strømgaard).

7.1. Introduction.

7.2. Ginkgolides and the PAF Receptor.

7.3. Ginkgolides and Glycine Receptors.

7.4. Various Effects of Ginkgolides.

7.5. Conclusions and Outlook.

Acknowledgment.

References.

8 Recent Progress in Calophyllum Coumarins as Potent Anti-HIV Agents (Lin Wang, Tao Ma, and Gang Liu).

8.1. Introduction.

8.2. Anti-HIV-1 Activity of Calophyllum Coumarins.

8.3. Pharmacology of Calanolides.

8.4. Preparation of Calophyllum Coumarins.

8.5. Structure Modification of Calanolides.

8.6. Conclusion.

References.

9 Recent Progress and Prospects on Plant-Derived Anti-HIV Agents and Analogs (Donglei Yu and Kuo-Hsiung Lee).

9.1. Introduction.

9.2. Khellactone Coumarin Analogs as Anti-HIV Agents.

9.3. Biphenyl Derivatives as Anti-HIV Agents.

9.4. Triterpene Betulinic Acid Derivatives as Anti-HIV Agents.

9.5. Conclusions.

Acknowledgments.

References.

10 Recent Progress on the Chemical Synthesis of Annonaceous Acetogenins and Their Structurally Modified Mimics (Tai-Shan Hu, Yu-Lin Wu, and Zhu-Jun Yao).

10.1. Introduction.

10.2. Total Synthesis of Mono-THF Acetogenins.

10.3. Total Synthesis of Bis-THF Acetogenins.

10.4. Total Synthesis of THP-Containing Acetogenins.

10.5. Design and Synthesis of Mimics of Acetogenins.

10.6. Summary.

References.

Index.

""…an in-depth resource for anyone concerned about natural products and their application in medicine...it provides concise information that is difficult to find in a compact format elsewhere."" (Clinical Chemistry, January 2007)

""…I can imagine this book being used in an interdisciplinary graduate course…[or] as a reference text."" (Journal of the American Chemical Society, September 13, 2006)

""The authors are to be commended on the excellent blending of chemical, biological, and pharmacologic data…highly recommended to all with an interest in medicinal natural products chemistry."" (Journal of Medicinal Chemistry, June 1, 2006)