Chirality in Drug Design and Synthesis - 1st Edition - ISBN: 9780121366704, 9781483288246

Chirality in Drug Design and Synthesis

1st Edition

Editors: C. Brown
eBook ISBN: 9781483288246
Imprint: Academic Press
Published Date: 20th November 1990
Page Count: 243
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Description

Chirality in Drug Design and Synthesis is a collection of papers that discusses the property of asymmetry in the structural and synthetic chemistry of natural products, including the significance of chirality in medicinal chemistry. These papers examine the need for the preparation and study of pure enantiomers of chiral drug substances and their mechanism of interaction with enzymes and receptors. These papers also investigate the techniques in studying these interactions, as well as analyze the methods for their synthesis in enantiomerically pure form. One paper discusses the pharmacological and pharmacokinetic analyses made that point to the differences in the activity and disposition of enantiometric pairs. Another paper reviews the implications of the neglect of stereoselectivity at the different levels during the examination process of racemic drugs. Since no general guidelines exists for the development of drugs with chiral centers, one paper suggests a case-by-case approach in evaluating the safety and efficacy of drugs, particularly as regards how isomers differ in their effects. This collection is suitable for the pharmacologist, medicinal chemists, toxicologists, mechanistic chemists and synthetic organic chemists.

Table of Contents


Contributors

Foreword

Introduction

1 Chirality: Pharmacological Action and Drug Development

1 Introduction

2 Terminology

3 Enantioselectivity in Pharmacological Activity

4 Enantioselectivity in Pharmacodynamics Resulting from Differences in the Pharmacokinetics of the Enantiomers

5 Conclusion

References

2 Racemic Therapeutics: Problems all Along the Line

1 Introduction

2 Implications of Chirality in Bioactive Agents

3 Clinical Pharmacology of Racemic Therapeutics

4 Ethical Aspects of Drug Development, Evaluation and Use

5 Noninformation and Disinformation in the Field of Chirality

6 Racemates as Drug Combinations

7 Perspectives

8 Summary

References

3 Chirality, Drug Metabolism and Action

1 Introduction

2 Stereochemistry and Drug Disposition

3 Stereoselective Metabolism and Drug Action

4 Conclusions

References

4 From Enzyme Mimics to Molecular Self-Assembly Processes

1 Introduction

2 A Gift from Nature

3 Needs of Enzyme Mimics

4 Serendipity Yet Again

5 A Chiral Crown Ether as a Reagent

6 The Same Chiral Crown Ether as a Catalyst

7 Coordination Through the Second Sphere

8 Planned Molecular Self-Assembly

9 From Host-Guest Chemistry to Molecular Assemblies

10 Structure-Directed Synthesis

11 The Future

Acknowledgments

References

5 Modeling of Drug-Receptor Interactions: Stereoselectivity of 5-Hydroxytryptamine and Dopamine Receptors in the Brain

1 Introduction

2 Interactions Between L-ZGP and 8-OH DPAT

3 Modeling of Drug-Receptor Interactions

4 DA D2-Receptor Agonists and Antagonists

5 5-HT1A-Receptor Agonists and Antagonists

Acknowledgments

References

6 Molecular Basis of the Activity of Antibiotics of the Vancomycin Group: Guides for Peptide-Peptide Binding

1 Introduction

2 Stereoselectivity

3 Peptide-Peptide Molecular Recognition

4 Approximate Binding Constants Estimated for Simple Carboxylic Acids

5 A Molecular Interpretation of the Binding Process

Acknowledgments

References

7 Recent Developments in the Use of Enzyme-catalysed Reactions in Organic Synthesis

1 Introduction

2 Recent Uses of Hydrolase Enzymes

3 Recent Uses of Oxidoreductase Enzymes

4 Enzyme-Catalysed Reactions Resulting in the Formation of Carbon-Carbon Bonds

5 Future Developments in the Area of Biotransformations

References

8 Recent Progress in Research on the Immunosuppressant FK-506

1 Isolation, Structure Determination and Stability of FK-506

2 Biological Activity

3 Synthetic Approaches to FK-506

References

9 A Practical, Enantioselective Synthesis of [R-(R,S)]-β-[(2-Carboxyethyl)thio]-α-hydroxy-2-(8-phenyloctyl)-benzenepropanoic acid (SK&F 104353), a Potent LTD4 Antagonist

1 Introduction

2 Background

3 Improvements in the Synthesis of 2-(phenyloctyl)benzaldehyde

4 Regioselective Epoxide Opening

5 Enantioselective Synthesis of an Epoxide Intermediate

6 Final Elaboration of SK&F 104353

Acknowledgments

References

10 Chirality Recognition in Synthesis

1 Introduction

2 Structure of the Chiral Iron Acetyl Complex [(C5H5)Fe(CO)(PPh3)COCH3]

3 Stereoselective Enolate Alkylation Reactions

4 Asymmetric Synthesis of Captopril and Epicaptopril

5 Asymmetric Synthesis of Differentially Protected α-alkylsuccinates

6 Asymmetric Synthesis of Actinonin and (—)-epiactinonin

7 Asymmetric Synthesis of Butyrolactones

8 Conclusions

Acknowledgments

References

11 Sultam-directed Asymmetric Synthesis of α-Amino Acids

1 Introduction

2 Alkylation of Glycinate Equivalents

3 Halogenation/Azide Displacement

4 Electrophilic 'Amination'

5 Conclusion

Acknowledgments

References

Appendix: Abstracts of Posters

Index

Details

No. of pages:
243
Language:
English
Copyright:
© Academic Press 1990
Published:
Imprint:
Academic Press
eBook ISBN:
9781483288246

About the Editor

C. Brown