New Synthetic Technologies in Medicinal Chemistry
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1 New Synthetic Technologies in Medicinal Chemistry Edited by Elizabeth Farrant Worldwide Medicinal Chemistry, Pfizer Ltd., Sandwich, Kent, UK
2 Chapter 1 Chapter 2 Introduction Elizabeth Farrant 1.1 Introduction 1.2 The Legacy of Combinatorial Chemistry 1.3 Case Study: Sorafenib 1.4 Conclusion References High Throughput Chemistry in Drug Discovery Andy Merritt 2.1 Introduction 2.2 The Potential of High Throughput Chemistry in Drug Discovery 2.3 The Start of Combichem in Drug Discovery 2.4 From Peptides to Small Molecules 2.5 My Library's Bigger Than Your Library: The 'Universal' Library 2.6 From Combichem to High Throughput Chemistry: Remembering It's All About Drugs 2.7 Technology to Make It Happen 2.8 Illustrative Approaches in Drug Discovery SAR Development using Parallel Chemistry Lead Discovery: Split and Mix Examples Dynamic Combinatorial Chemistry: From Fragments to Libraries 1 I I RSC Drug Discovery Series No. II New Synthetic Technologies in Medicinal Chemistry Edited by Elizabeth Farrant
3 4.1 Introduction An Overview of Microwave Theory How Do Microwaves Enhance Chemical Reactions? Microwave Heating An Overview of Commercial Microwave Reactors Current Applications of Microwave Assisted Synthesis Metal-catalysed Reactions SNAr reactions: Rate and Purity Enhancements Reactions Utilising a Gaseous Reagent Transfer Hydrogenations 77, ,0 X Other Approaches and Uses of Combinatorial Chemistry in Drug Discovery Conclusion 34 References 35 Chapter 3 High Throughput Reaction Screening 42 Andrew I. Morrell 3.1 Introduction High Throughput Reaction Screening Statistical Design of Experiments in Reaction Screening Suzuki-Miyaura Reaction Catalyst Screening Heck Reaction Catalyst Screening Hydrogenation Catalyst Screening Biotransformation Reaction Screening Reaction Screening Using Continuous Processes High Throughput Salt Screening High Throughput Solubility Screening Equipment and Automation Used in High Throughput Reaction Screening Analytical Techniques Used in High Throughput Reaction Screening Conclusion 61 References 61 Chapter 4 Microwave Assisted Chemistry 63 Rachel Osborne
4 5.1 Introduction Benefits of Flow Chemistry Thermal Control Mixing Stoichiometric Control and Selectivity Safety Enhanced Process Parameters Hazardous Reactions Multistep Processes Limitations and Technology Hurdles Solubility of Reagents Solubility of Products Scale Other Issues Flow Dynamics: Some Basic Theory Reynolds Number Laminar Flow Turbulent Flow Parabolic and Plug Flow Residence Time Distribution Electroosmotic Flow Experimental Set-up Pumps Mixing The Reactor Sample Collection Converting a Process from Batch to Flow Packed Bed Reactors Published Chemistry Examples Hazardous Reagents Exothermic Reactions Unstable Intermediates Selectivity "Click Chemistry" Reactions Utilising Solid-supported Reagents Parallel Synthesis Multi-gram Scale Reactions Conclusion 87 References 87 XI Chapter 5 Continuous Flow Chemistry in Medicinal Chemistry 90 Martyn Deal
5 xii 5.9 Integrating Continuous Flow with Other Technologies 1 I Microwaves Other Technologies Beyond Synthesis Liquid- Liquid Extraction Purification Continuous Flow Crystallisation Conclusion 121 References 122 Chapter 6 Emerging Synthetic Technologies Brian H. Warrington Introduction Template Guided Systems Overview Dynamic Combinatorial Chemistry Click Chemistry sirna Approaches Knowledge-based Iterative Systems I Overview New Tools for Iterative Working Fast and Efficient Realisation of Novel Leads: Rescaling the Process Prediction of Unforeseen Structures Challenges for High Speed Iterative Chemistry Directed Assembly using DNA Conclusion 148 References l 49 Subject Index 154
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