Privileged scaffolds in medicinal chemistry : design, synthesis, evaluation / editor: Stefan Bräse.

Format
Book
Language
English
Published/​Created
  • [Cambridge] : Royal Society of Chemistry, [2015]
  • ©2016
Description
1 online resource (570 pages).

Details

Subject(s)
Editor
Series
Summary note
One strategy to expedite the discovery of new drugs, a process that is somewhat slow and serendipitous, is the identification and use of privileged scaffolds. This book covers the history of the discovery and use of privileged scaffolds and addresses the various classes of these important molecular fragments. The first of the benzodiazepines, a class of drugs that is powerful for treating anxiety, may not have been discovered had it not been for a chance experiment on the contents of a discarded flask found during a lab clean-up. Some years later, scientists discovered that benzodiazepine derivatives were also effective in treating other diseases. This class of molecules was the first to be described as privileged in the sense that it is especially effective at altering the course of disease. Other privileged molecular structures have since been discovered, and since these compounds are so effective at interacting with numerous classes of proteins, they may be an effective starting point to look for new drugs against the supposedly ₃undruggable₄ proteins. Following introductory chapters presenting an overview, a historical perspective and the theoretical background and findings, main chapters describe the structure of privileged structures in turn and discuss major drug classes associated with them and their syntheses. This book provides comprehensive coverage of the subject through chapters contributed by expert authors from both academia and industry and will be an excellent reference source for medicinal chemists of a range of disciplines and experiences.
Notes
  • Includes index.
  • Title from title details screen (Royal Society of Chemistry, viewed December 14, 2015).
Contents
  • Cover; Preface; Contents; Chapter 1 Privileged Scaffolds in Medicinal Chemistry: An Introduction; 1.1 Introduction; 1.2 The Privileged Scaffolds in Drug Discovery; 1.3 Conclusion; Acknowledgments; References; Chapter 2 Privileged Scaffolds in Medicinal Chemistry
  • A Computational Approach; 2.1 Introduction; 2.2 Scope of the Study; 2.3 Privileged Scaffolds; 2.4 Molecular Docking; 2.5 Protein Structure Prediction; 2.5.1 Comparative Modeling; 2.5.2 Threading (Fold Recognition); 2.5.3 Model Building and Refinement; 2.5.4 Loop Modeling; 2.5.5 Side Chain Modeling; 2.5.6 Model Building
  • 2.5.7 Model Quality Assessment2.5.8 Ab Initio Prediction; 2.5.9 Critical Assessment of Techniques for Protein Structure Prediction (CASP); 2.6 Molecular Docking Methodology; 2.6.1 Receptor Representation; 2.6.2 Docking Algorithms; 2.6.3 Scoring Functions; 2.7 Fragment-based Drug Design; 2.8 Structure-based Virtual Screening; 2.9 Applications of Modeling to Privileged Scaffolds; 2.9.1 Benzimidazole; 2.9.2 Coumarins; 2.10 Outlook and Challenges; References; Chapter 3 The β-Lactam (Azetidin-2-one) as a Privileged Ring in Medicinal Chemistry ; 3.1 Introduction
  • 3.2 Stability and Reactivity of the β-Lactam 3.3 Synthesis of the β-Lactams ; 3.3.1 The Sheehan and Henery-Logan Synthesis of Protected 6-Aminopenicillanic Acid; 3.3.2 Synthesis of 4-Oxo-2-azetidinecarboxylic Acid from Aspartate; 3.3.3 Synthesis of the Protected Taxoid Sidechains: (3R,4S)-3-Hydroxy-2-oxo-1-Azetidinecarboxylic Acid Esters; 3.3.4 Synthetic Application of the 6-Azabicyclo[3.2.0]hept-3-en-7-one Enantiomers; 3.3.5 Recent Syntheses of Ezetimibe; 3.3.6 Carbapenem Synthesis; 3.4 Structure of the β-Lactams ; 3.5 Biological Target Profiling of the β-Lactam
  • 3.6 The Antibacterial β-Lactam 3.6.1 The Bicyclic β-Lactam Antibacterials ; 3.6.2 The Monocyclic β-Lactam Antibacterials ; 3.6.3 β-Lactamase Inhibitors ; 3.6.4 Non-PBP Targeting by Antibacterial β-Lactam Structures ; 3.7 The Non-antibacterial β-Lactam in Medicinal Chemistry ; 3.8 Resurgence of the β-Lactam ; References; Chapter 4 (Benz)imidazoles; 4.1 General Considerations About (Benz)imidazoles; 4.1.1 Physico-chemical Properties of (Benz)imidazoles; 4.1.2 (Benz)imidazoles As Scaffolds: Geometry and Options For Interaction; 4.1.3 Synthesis of (Benz)imidazoles
  • 4.1.4 Natural Products Containing (Benz)imidazoles4.2 Case Studies of Marketed Drugs; 4.2.1 Angiotensin II Receptor Antagonists; 4.2.2 H+, K+-ATPase Inhibitors; 4.2.3 H1-antihistamines; 4.2.4 Anthelmintics; 4.2.5 Miscellaneous; References; Chapter 5 Pyrazoles; 5.1 General Remarks about Pyrazoles; 5.1.1 Physicochemical Properties of Pyrazoles; 5.1.2 Synthesis of Pyrazoles; 5.1.3 Natural Products Containing Pyrazoles; 5.2 (Former) Marketed Drugs; 5.2.1 Anti-inflammatory Drugs; 5.2.2 Vasodilators; 5.2.3 Tyrosine-kinase-inhibitors; 5.2.4 Cannabinoid-receptor-antagonists
ISBN
  • 9781782622246 ((electronic bk.))
  • 1782622241 ((electronic bk.))
  • 9781782627791 ((electronic bk.))
  • 1782627790 ((electronic bk.))
OCLC
932123727
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