Steroid Dimers

Professor Satyajit D Sarker BPharm (Hons) MPharm PhD FHEA, Professor of Pharmacy, Department of Pharmacy, School of Applied Sciences, University of Wolverhampton, UKProfessor 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 MRSCDepartment of Pharmacy, School of Applied Sciences, University of Wolverhampton, UK.

• Preface ix List of Abbreviations xi1 Introduction 11.1 Steroids and Steroid Dimers 11.2 General Physical and Spectroscopic Properties of Steroid Dimers 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 Analogues 2875.1 Introduction 2875.2 Synthesis of Cephalostatin and Ritterazine Analogues 2885.3 Total Synthesis of Naturally Occurring Cephalostatin 1 371References 3766 Applications of Steroid Dimers 3796.1 Application of Steroid Dimers as ‘Molecular Umbrellas’: 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 Serum Cholesterol Level 4016.2.4 Effect on Bilayer Lipid Membranes 4026.2.5 Supramolecular Transmembrane Ion Channels, and Artificial Receptors and Ionophores 4026.2.6 Other Properties 404References 405Index 409