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Bioisosteres in medicinal chemistry

Author: Nathan Brown, (Medicinal chemist)
Publisher: Weinheim, Germany : Wiley-VCH, ©2012.
Series: Methods and principles in medicinal chemistry, v. 54.
Edition/Format:   Book : EnglishView all editions and formats
Database:WorldCat
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Written with the practicing medicinal chemist in mind, this is the first modern handbook to systematically address the topic of bioisosterism. As such, it provides a ready reference on the principles  Read more...

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Document Type: Book
All Authors / Contributors: Nathan Brown, (Medicinal chemist)
ISBN: 9783527330157 3527330151 9783527654338 352765433X 9783527654321 3527654321 9783527654314 3527654313 9783527654307 3527654305
OCLC Number: 822991552
Description: xviii, 237 p. : ill. (some col.) ; 25 cm.
Contents: List of Contributors XI Preface XV A Personal Foreword XVII Part One Principles 1 1 Bioisosterism in Medicinal Chemistry 3 Nathan Brown 1.1 Introduction 3 1.2 Isosterism 3 1.3 Bioisosterism 6 1.4 Bioisosterism in Lead Optimization 9 1.5 Conclusions 13 References 14 2 Classical Bioisosteres 15 Caterina Barillari and Nathan Brown 2.1 Introduction 15 2.2 Historical Background 15 2.3 Classical Bioisosteres 17 2.4 Nonclassical Bioisosteres 20 2.5 Summary 27 References 27 3 Consequences of Bioisosteric Replacement 31 Dennis A. Smith and David S. Millan 3.1 Introduction 31 3.2 Bioisosteric Groupings to Improve Permeability 32 3.3 Bioisosteric Groupings to Lower Intrinsic Clearance 40 3.4 Bioisosteric Groupings to Improve Target Potency 43 3.5 Conclusions and Future Perspectives 47 References 49 Part Two Data 53 4 BIOSTER: A Database of Bioisosteres and Bioanalogues 55 Istvan Ujvary and Julian Hayward 4.1 Introduction 55 4.2 Historical Overview and the Development of BIOSTER 56 4.3 Description of BIOSTER Database 59 4.4 Examples 64 4.5 Applications 69 4.6 Summary 70 4.7 Appendix 70 References 71 5 Mining the Cambridge Structural Database for Bioisosteres 75 Colin R. Groom, Tjelvar S. G. Olsson, John W. Liebeschuetz, David A. Bardwell, Ian J. Bruno, and Frank H. Allen 5.1 Introduction 75 5.2 The Cambridge Structural Database 76 5.3 The Cambridge Structural Database System 78 5.4 The Relevance of the CSD to Drug Discovery 83 5.5 Assessing Bioisosteres: Conformational Aspects 84 5.6 Assessing Bioisosteres: Nonbonded Interactions 86 5.7 Finding Bioisosteres in the CSD: Scaffold Hopping and Fragment Linking 91 5.8 A Case Study: Bioisosterism of 1 H -Tetrazole and Carboxylic Acid Groups 94 5.9 Conclusions 97 References 98 6 Mining for Context-Sensitive Bioisosteric Replacements in Large Chemical Databases 103 George Papadatos, Michael J. Bodkin, Valerie J. Gillet, and Peter Willett 6.1 Introduction 103 6.2 Definitions 104 6.3 Background 105 6.4 Materials and Methods 109 6.5 Results and Discussion 113 6.6 Conclusions 124 References 125 Part Three Methods 129 7 Physicochemical Properties 131 Peter Ertl 7.1 Introduction 131 7.2 Methods to Identify Bioisosteric Analogues 132 7.3 Descriptors to Characterize Properties of Substituents and Spacers 132 7.4 Classical Methods for Navigation in the Substituent Space 135 7.5 Tools to Identify Bioisosteric Groups Based on Similarity in Their Properties 136 7.6 Conclusions 138 References 138 8 Molecular Topology 141 Nathan Brown 8.1 Introduction 141 8.2 Controlled Fuzziness 141 8.3 Graph Theory 142 8.4 Data Mining 144 8.5 Topological Pharmacophores 146 8.6 Reduced Graphs 149 8.7 Summary 151 References 152 9 Molecular Shape 155 Pedro J. Ballester and Nathan Brown 9.1 Methods 156 9.2 Applications 161 9.3 Future Prospects 164 References 165 10 Protein Structure 167 James E. J. Mills 10.1 Introduction 167 10.2 Database of Ligand--Protein Complexes 168 10.3 Generation of Ideas for Bioisosteres 173 10.4 Context-Specific Bioisostere Generation 177 10.5 Using Structure to Understand Common Bioisosteric Replacements 178 10.6 Conclusions 180 References 180 Part Four Applications 183 11 The Drug Guru Project 185 Kent D. Stewart, Jason Shanley, Karam B. Alsayyed Ahmed, and J. Phillip Bowen 11.1 Introduction 185 11.2 Implementation of Drug Guru 187 11.3 Bioisosteres 188 11.4 Application of Drug Guru 194 11.5 Quantitative Assessment of Drug Guru Transformations 195 11.6 Related Work 197 11.7 Summary: The Abbott Experience with the Drug Guru Project 197 References 198 12 Bioisosteres of an NPY-Y5 Antagonist 199 Nicholas P. Barton and Benjamin R. Bellenie 12.1 Introduction 199 12.2 Background 199 12.3 Potential Bioisostere Approaches 201 12.4 Template Molecule Preparation 204 12.5 Database Molecule Preparation 206 12.6 Alignment and Scoring 206 12.7 Results and Monomer Selection 207 12.8 Synthesis and Screening 208 12.9 Discussion 209 12.10 SAR and Developability Optimization 211 12.11 Summary and Conclusion 214 References 214 13 Perspectives from Medicinal Chemistry 217 Nicholas A. Meanwell, Marcus Gastreich, Matthias Rarey, Mike Devereux, Paul L.A. Popelier, Gisbert Schneider, and Peter Willett 13.1 Introduction 217 13.2 Pragmatic Bioisostere Replacement in Medicinal Chemistry: A Software Maker's Viewpoint 219 13.3 The Role of Quantum Chemistry in Bioisostere Prediction 221 13.4 Learn from "Naturally Drug-Like" Compounds 223 13.5 Bioisosterism at the University of Sheffield 224 References 227 Index 231
Series Title: Methods and principles in medicinal chemistry, v. 54.
Responsibility: edited by Nathan Brown.
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"In all, I believe this book is a musthave handbook on bioisosteres. It is highly valuable both as a text book for graduate students and as a book of reference for the medicinal chemist working in Read more...

 
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