ISBN-10:
0470746572
ISBN-13:
9780470746578
Pub. Date:
06/05/2012
Publisher:
Wiley
Steroid Dimers: Chemistry and Applications in Drug Design and Delivery / Edition 1

Steroid Dimers: Chemistry and Applications in Drug Design and Delivery / Edition 1

by Satyajit Sarker, Lutfun Nahar

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Overview

Steroid Dimers: Chemistry and Applications in Drug Design and Delivery / Edition 1

Steroid dimers are an important group of compounds produced byvarious marine organisms, and also synthesized in the laboratories.This group of compounds possesses various pharmacological andbiological properties, and can also be used to create “molecular umbrellas” for drug delivery.

Steroid Dimers: Chemistry and Applications in Drug Design andDelivery provides an up-to-date overview on the chemistry andapplications of steroid dimers of natural and synthetic origins.The book includes easy-to-follow synthetic protocols for variousclasses of important dimeric steroids, source details, valuablespectroscopic data and depiction of unique structural features ofnatural steroidal dimers, and the Structure-Activity-Relationships(SARs) of some pharmacologically active dimeric steroids. Topicscovered include:

  • introduction to steroid dimers
  • synthesis and chemistry of noncyclic and cyclic steroiddimers
  • naturally occurring steroid dimers – cephalostatins,ritterazines and crellastatins
  • biological and pharmacological functions of steroid dimers andtheir application in drug design and discovery
  • steroid dimers as “molecular umbrellas” for drugdelivery
Steroid Dimers: Chemistry and Applications in Drug Design andDelivery is an essential guide to this important class ofnatural and synthetic compounds for researchers and students ofnatural products chemistry and biochemistry, synthetic organicand  medicinal chemistry, and drug design, discovery anddelivery.

Product Details

ISBN-13: 9780470746578
Publisher: Wiley
Publication date: 06/05/2012
Pages: 440
Product dimensions: 6.70(w) x 10.00(h) x 1.00(d)

About the Author

Professor Satyajit D Sarker BPharm (Hons) MPharm PhD FHEA, Professor of Pharmacy, Department of Pharmacy, School of Applied Sciences, University of Wolverhampton, UK
Professor Sarker is the author of Natural Products Isolation (Humana Press), and, with Dr Nahar, of Chemistry for Pharmacy Students (Wiley). His research interests include the isolation, characterisation, bioactivity and mode of action of bioactive natural products, the metabolomics of medicinal plants, and quality control of herbal medicines.

Dr Lutfun Nahar BSc (Hons) PhD MRSC
Department of Pharmacy, School of Applied Sciences, University of Wolverhampton, UK.

Table of Contents

Preface ix

List of Abbreviations xi

1 Introduction 1

1.1 Steroids and Steroid Dimers 1

1.2 General Physical and Spectroscopic Properties of SteroidDimers 2

1.3 Chromatographic Behaviour of Steroid Dimers 5

1.4 Applications of Steroid Dimers 6

References 6

2 Synthesis of Acyclic Steroid Dimers 7

2.1 Dimers via Ring A–Ring A Connection 7

2.1.1 Direct Connection 7

2.1.2 Through Spacer Groups 21

2.2 Dimers via Ring B–Ring B Connection 68

2.2.1 Direct Connection 68

2.2.2 Through Spacer Groups 74

2.3 Dimers via Ring C–Ring C Connection 84

2.3.1 Through Spacer Groups 84

2.4 Dimers via Ring D–Ring D Connection 87

2.4.1 Direct Connection 87

2.4.2 Through Spacer Groups 89

2.4.3 Through Side Chain and Spacer Groups 100

2.5 Dimers via Ring A–Ring D Connection 151

2.5.1 Direct Connection 151

2.6 Dimers via Connection of C-19 169

2.7 Molecular Umbrellas 170

2.8 Miscellaneous 174

References 182

3 Synthesis of Cyclic Steroid Dimers 187

3.1 With Spacer Groups: Cholaphanes 187

3.2 Without Spacer Groups: Cyclocholates 232

References 238

4 Naturally Occurring Steroid Dimers 241

4.1 Cephalostatins 242

4.2 Crellastatins 254

4.3 Ritterazines 262

4.4 Others 277

References 284

5 Synthesis of Cephalostatin and Ritterazine Analogues287

5.1 Introduction 287

5.2 Synthesis of Cephalostatin and Ritterazine Analogues 288

5.3 Total Synthesis of Naturally Occurring Cephalostatin 1371

References 376

6 Applications of Steroid Dimers 379

6.1 Application of Steroid Dimers as ‘MolecularUmbrellas’: Drug Delivery 379

6.2 Biological and Pharmacological Functions of Steroid Dimers:Drug Discovery and Design 382

6.2.1 Antimalarial Activity 383

6.2.2 Cytotoxicity and Anticancer Potential 386

6.2.3 Effect on Micellar Concentrations of Bile Salts and SerumCholesterol Level 401

6.2.4 Effect on Bilayer Lipid Membranes 402

6.2.5 Supramolecular Transmembrane Ion Channels, and ArtificialReceptors and Ionophores 402

6.2.6 Other Properties 404

References 405

Index 409

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