Steroid Dimers

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.

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 - cephalostatinsritterazines and crellastatins* biological and pharmacological functions of steroid dimers andtheir application in drug design and discovery* steroid dimers as "molecular umbrellas" for drugdeliverySteroid 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.

Preface ixList of Abbreviations xi1 Introduction 11.1 Steroids and Steroid Dimers 11.2 General Physical and Spectroscopic Properties of SteroidDimers 21.3 Chromatographic Behaviour of Steroid Dimers 51.4 Applications of Steroid Dimers 6References 62 Synthesis of Acyclic Steroid Dimers 72.1 Dimers via Ring A-Ring A Connection 72.1.1 Direct Connection 72.1.2 Through Spacer Groups 212.2 Dimers via Ring B-Ring B Connection 682.2.1 Direct Connection 682.2.2 Through Spacer Groups 742.3 Dimers via Ring C-Ring C Connection 842.3.1 Through Spacer Groups 842.4 Dimers via Ring D-Ring D Connection 872.4.1 Direct Connection 872.4.2 Through Spacer Groups 892.4.3 Through Side Chain and Spacer Groups 1002.5 Dimers via Ring A-Ring D Connection 1512.5.1 Direct Connection 1512.6 Dimers via Connection of C-19 1692.7 Molecular Umbrellas 1702.8 Miscellaneous 174References 1823 Synthesis of Cyclic Steroid Dimers 1873.1 With Spacer Groups: Cholaphanes 1873.2 Without Spacer Groups: Cyclocholates 232References 2384 Naturally Occurring Steroid Dimers 2414.1 Cephalostatins 2424.2 Crellastatins 2544.3 Ritterazines 2624.4 Others 277References 2845 Synthesis of Cephalostatin and Ritterazine Analogues2875.1 Introduction 2875.2 Synthesis of Cephalostatin and Ritterazine Analogues 2885.3 Total Synthesis of Naturally Occurring Cephalostatin 1371References 3766 Applications of Steroid Dimers 3796.1 Application of Steroid Dimers as 'MolecularUmbrellas': Drug Delivery 3796.2 Biological and Pharmacological Functions of Steroid Dimers:Drug Discovery and Design 3826.2.1 Antimalarial Activity 3836.2.2 Cytotoxicity and Anticancer Potential 3866.2.3 Effect on Micellar Concentrations of Bile Salts and SerumCholesterol Level 4016.2.4 Effect on Bilayer Lipid Membranes 4026.2.5 Supramolecular Transmembrane Ion Channels, and ArtificialReceptors and Ionophores 4026.2.6 Other Properties 404References 405Index 409