Steroid Dimers Chemistry and Applications in Drug Design and Delivery

by Sarker, Professor Satyajit D.; Nahar, Lutfun

• ISBN13: 9780470746578
• ISBN10: 0470746572
• Edition: 1st
• Format: Hardcover
• Copyright: 2012-05-29
• Publisher: Wiley

Summary

Steroid dimers are an important group of compounds produced by various marine organisms, and also synthesized in the laboratories. This group of compounds possesses various pharmacological and biological properties, and can also be used to create "molecular umbrellas" for drug delivery. Steroid Dimers: Chemistry and Applications in Drug Design and Delivery provides an up-to-date overview on the chemistry and applications of steroid dimers of natural and synthetic origins. The book includes easy-to-follow synthetic protocols for various classes of important dimeric steroids, source details, valuable spectroscopic data and depiction of unique structural features of natural steroidal dimers, and the Structure-Activity-Relationships (SARs) of some pharmacologically active dimeric steroids. Topics covered include: introduction to steroid dimers synthesis and chemistry of noncyclic and cyclic steroid dimers naturally occurring steroid dimers cephalostatins, ritterazines and crellastatins biological and pharmacological functions of steroid dimers and their application in drug design and discovery steroid dimers as "molecular umbrellas" for drug delivery Steroid Dimers: Chemistry and Applications in Drug Design and Delivery is an essential guide to this important class of natural and synthetic compounds for researchers and students of natural products chemistry and biochemistry, synthetic organic and medicinal chemistry, and drug design, discovery and delivery.

Author Biography

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	p. ix
List of Abbreviations	p. xi
Introduction	p. 1
Steroids and Steroid Dimers	p. 1
General Physical and Spectroscopic Properties of Steroid Dimers	p. 2
Chromatographic Behaviour of Steroid Dimers	p. 5
Applications of Steroid Dimers	p. 6
References	p. 6
Synthesis of Acyclic Steroid Dimers	p. 7
Dimers via Ring A-Ring A Connection	p. 7
Direct Connection	p. 7
Through Spacer Groups	p. 21
Dimers via Ring B-Ring B Connection	p. 68
Direct Connection	p. 68
Through Spacer Groups	p. 74
Dimers via Ring C-Ring C Connection	p. 84
Through Spacer Groups	p. 84
Dimers via Ring D-Ring D Connection	p. 87
Direct Connection	p. 87
Through Spacer Groups	p. 89
Through Side Chain and Spacer Groups	p. 100
Dimers via Ring A-Ring D Connection	p. 151
Direct Connection	p. 151
Dimers via Connection of C-19	p. 169
Molecular Umbrellas	p. 170
Miscellaneous	p. 174
References	p. 182
Synthesis of Cyclic Steroid Dimers	p. 187
With Spacer Groups: Cholaphanes	p. 187
Without Spacer Groups: Cyclocholates	p. 232
References	p. 238
Naturally Occurring Steroid Dimers	p. 241
Cephalostatins	p. 242
Crellastatins	p. 254
Ritterazines	p. 262
Others	p. 277
References	p. 284
Synthesis of Cephalostatin and Ritterazine Analogues	p. 287
Introduction	p. 287
Synthesis of Cephalostatin and Ritterazine Analogues	p. 288
Total Synthesis of Naturally Occurring Cephalostatin 1	p. 371
References	p. 376
Applications of Steroid Dimers	p. 379
Application of Steroid Dimers as 'Molecular Umbrellas': Drug Delivery	p. 379
Biological and Pharmacological Functions of Steroid Dimers: Drug Discovery and Design	p. 382
Antimalarial Activity	p. 383
Cytotoxicity and Anticancer Potential	p. 386
Effect on Micellar Concentrations of Bile Salts and Serum Cholesterol Level	p. 401
Effect on Bilayer Lipid Membranes	p. 402
Supramolecular Transmembrane Ion Channels, and Artificial Receptors and Ionophores	p. 402
Other Properties	p. 404
References	p. 405
Index	p. 409
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