UID:
almahu_9948198528102882
Format:
1 online resource
ISBN:
9781119092582
,
1119092582
,
9781119092902
,
1119092906
,
9781119092599
,
1119092590
Note:
Foreword xiii -- Introduction xv -- About the Contributors xix -- Part I Challenges Specific to Macrocycles 1 -- 1 Contemporary Macrocyclization Technologies 3 / Serge Zaretsky and Andrei K. Yudin -- 1.1 Introduction 3 -- 1.2 Challenges Inherent to the Synthesis of Macrocycles 3 -- 1.3 Challenges in Macrocycle Characterization 6 -- 1.4 Macrocyclization Methods 8 -- 1.5 Cyclization on the Solid Phase 14 -- 1.6 Summary 17 -- References 18 -- 2 A Practical Guide to Structural Aspects of Macrocycles (NMR, X-Ray, and Modeling) 25 / David J. Craik, Quentin Kaas and Conan K. Wang -- 2.1 Background 25 -- 2.2 Experimental Studies of Macrocycles 31 -- 2.3 Molecular Modeling of Macrocyclic Peptides 38 -- 2.4 Summary 46 -- Acknowledgments 47 -- References 47 -- 3 Designing Orally Bioavailable Peptide and Peptoid Macrocycles 59 / David A. Price, Alan M. Mathiowetz and Spiros Liras -- 3.1 Introduction 59 -- 3.2 Improving Peptide Plasma Half-Life 60 -- 3.3 Absorption, Bioavailability, and Methods for Predicting Absorption 61 -- 3.4 In Silico Modeling 70 -- 3.5 Future Directions 71 -- References 72 -- Part II Classes of Macrocycles and Their Potential for Drug Discovery 77 -- 4 Natural and Nature-Inspired Macrocycles: A Chemoinformatic Overview and Relevant Examples 79 / Ludger A. Wessjohann, Richard Bartelt and Wolfgang Brandt -- 4.1 Introduction to Natural Macrocycles as Drugs and Drug Leads 79 -- 4.2 Biosynthetic Pathways, Natural Role, and Biotechnological Access 79 -- 4.3 QSAR and Chemoinformatic Analyses of Common Features 84 -- 4.4 Case Studies: Selected Natural Macrocycles of Special Relevance in Medicinal Chemistry 88 -- References 91 -- 5 Bioactive and Membrane-Permeable Cyclic Peptide Natural Products 101 / Andrew T. Bockus and R. Scott Lokey -- 5.1 Introduction 101 -- 5.2 Structural Motifs and Permeability of Cyclic Peptide Natural Products 101 -- 5.3 Conformations of Passively Permeable Bioactive Cyclic Peptide Natural Products 103 -- 5.4 Recently Discovered Bioactive Cyclic Peptide Natural Products 108 -- 5.5 Conclusions 125 -- References 125 -- 6 Chemical Approaches to Macrocycle Libraries 133 / Ziqing Qian, Patrick G. Dougherty and Dehua Pei -- 6.1 Introduction 133 -- 6.2 Challenges Associated with Macrocyclic One-Bead-One-Compound Libraries 134 -- 6.3 Deconvolution of Macrocyclic Libraries 134 -- 6.4 Peptide-Encoded Macrocyclic Libraries 136 -- 6.5 DNA- Encoded Macrocyclic Libraries 142 -- 6.6 Parallel Synthesis of Macrocyclic Libraries 142 -- 6.7 Diversity- Oriented Synthesis 145 -- 6.8 Perspective 147 -- 6.9 Conclusion 149 -- References 150 -- 7 Biological and Hybrid Biological/Chemical Strategies in Diversity Generation of Peptidic Macrocycles 155 / Francesca Vitali and Rudi Fasan -- 7.1 Introduction 155 -- 7.2 Cyclic Peptide Libraries on Phage Particles 155 -- 7.3 Macrocyclic Peptide Libraries via In Vitro Translation 166 -- 7.4 Emerging Strategies for the Combinatorial Synthesis of Hybrid Macrocycles In Vitro and in Cells 171 -- 7.5 Comparative Analysis of Technologies 175 -- 7.6 Conclusions 178 -- References 178 -- 8 Macrocycles for Protein -Protein Interactions 185 / Eilidh Leitch and Ali Tavassoli -- 8.1 Introduction 185 -- 8.2 Library Approaches to Macrocyclic PPI Inhibitors 186 -- 8.3 Structural Mimicry 192 -- 8.4 Multi- Cycles for PPIs 197 -- 8.5 The Future for Targeting PPIs with Macrocycles 197 -- References 200 -- Part III The Synthetic Toolbox for Macrocycles 205 -- 9 Synthetic Strategies for Macrocyclic Peptides 207 / & Eric Biron, Simon Vezina-Dawod and François Bédard -- 9.1 Introduction to Peptide Macrocyclization 207 -- 9.2 One Size Does Not Fit All: Factors to Consider During Synthesis Design 209 -- 9.3 Peptide Macrocyclization in Solution 213 -- 9.4 Peptide Macrocyclization on Solid Support 220 -- 9.5 Peptide Macrocyclization by Disulfide Bond Formation 226 -- 9.6 Conclusion 229 -- References 230 -- 10 Ring-Closing Metathesis-Based Methods in Chemical Biology: Building a Natural Product Inspired Macrocyclic Toolbox to Tackle Protein -Protein Interactions 243 / Jagan Gaddam, Naveen Kumar Mallurwar, Saidulu Konda, Mahender Khatravath, Madhu Aeluri, Prasenjit Mitra and Prabhat Arya -- 10.1 Introduction 243 -- 10.2 Protein -- Protein Interactions: Challenges and Opportunities 243 -- 10.3 Natural Products as Modulators of Protein -Protein Interactions 243 -- 10.4 Introduction to Ring-Closing Metathesis 244 -- 10.5 Selected Examples of Synthetic Macrocyclic Probes Using RCM-Based Approaches 246 -- 10.6 Summary 259 -- References 259 -- 11 The Synthesis of Peptide-Based Macrocycles by Huisgen Cycloaddition 265 / Ashok D. Pehere and Andrew D. Abell -- 11.1 Introduction 265 -- 11.2 Dipolar Cycloaddition Reactions 266 -- 11.3 Macrocyclic Peptidomimetics 267 -- 11.4 Macrocyclic & beta;-Strand Mimetics as Cysteine Protease Inhibitors 273 -- 11.5 Conclusion 275 -- References 277 -- 12 Palladium-Catalyzed Synthesis of Macrocycles 281 / Thomas O. Ronson, William P. Unsworth and Ian J.S. Fairlamb -- 12.1 Introduction 281 -- 12.2 Stille Reaction 281 -- 12.3 Suzuki -- Miyaura Reaction 285 -- 12.4 Heck Reaction 288 -- 12.5 Sonogashira Reaction 290 -- 12.6 Tsuji -- Trost Reaction 293 -- 12.7 Other Reactions 295 -- 12.8 Conclusion 298 -- References 298 -- 13 Alternative Strategies for the Construction of Macrocycles 307 / Jeffrey Santandrea, Anne-Catherine Bédard, Mylène de Léséleuc, Michaël Raymond and Shawn K. Collins -- 13.1 Introduction 307 -- 13.2 Alternative Methods for Macrocyclization Involving Carbon -Carbon Bond Formation 307 -- 13.3 Alternative Methods for Macrocyclization Involving Carbon -Carbon Bond Formation: Ring Expansion and Photochemical Methods 320 -- 13.4 Alternative Methods for Macrocyclization Involving Carbon -Oxygen Bond Formation 322 -- 13.5 Alternative Methods for Macrocyclization Involving Carbon -Nitrogen Bond Formation 327 -- 13.6 Alternative Methods for Macrocyclization Involving Carbon -Sulfur Bond Formation 328 -- 13.7 Conclusion and Summary 331 -- References 332 -- 14 Macrocycles from Multicomponent Reactions 339 / Ludger A. Wessjohann, Ricardo A.W. Neves Filho, Alfredo R. Puentes and Micjel Chávez Morejón -- 14.1 Introduction 339 -- 14.2 General Aspects of Multicomponent Reactions (MCRs) in Macrocycle Syntheses 344 -- 14.3 Concluding Remarks and Future Perspectives 369 -- References 371 -- 15 Synthetic Approaches Used in the Scale-Up of Macrocyclic Clinical Candidates 377 / Jongrock Kong -- 15.1 Introduction 377 -- 15.2 Background 377 -- 15.3 Literature Examples 378 -- 15.4 Conclusions 406 -- References 406 -- Part IV Macrocycles in Drug Development: Case Studies 411 -- 16 Overview of Macrocycles in Clinical Development and Clinically Used 413 / Silvia Stotani and Fabrizio Giordanetto -- 16.1 Introduction 413 -- 16.2 Datasets Generation 413 -- 16.3 Marketed Macrocyclic Drugs 414 -- 16.4 Macrocycles in Clinical Studies 422 -- 16.5 De Novo Designed Macrocycles 429 -- 16.6 Overview and Conclusions 436 -- Appendix 16.A 437 -- 16.A.1 Methods 437 -- References 490 -- 17 The Discovery of Macrocyclic IAP Inhibitors for the Treatment of Cancer 501 / Nicholas K. Terrett -- 17.1 Introduction 501 -- 17.2 DNA-Programmed Chemistry Macrocycle Libraries 502 -- 17.3 A New Macrocycle Ring Structure 504 -- 17.4 Design and Profiling of Bivalent Macrocycles 506 -- 17.5 Improving the Profile of the Bivalent Macrocycles 510 -- 17.6 Selection of the Optimal Bivalent Macrocyclic IAP Antagonist 512 -- 17.7 Summary 515 -- Acknowledgments 515 -- References 516 -- 18 Discovery and Pharmacokinetic -Pharmacodynamic Evaluation of an Orally Available Novel Macrocyclic Inhibitor of Anaplastic Lymphoma Kinase and c-Ros Oncogene 1 519 / Shinji Yamazaki, Justine L. Lam and Ted W.
,
Johnson -- 18.1 Introduction 519 -- 18.2 Discovery and Synthesis 520 -- 18.3 Evaluation of Pharmacokinetic Properties Including CNS Penetration 531 -- 18.4 Evaluation of Pharmacokinetic -Pharmacodynamic (PKPD) Profiles 536 -- 18.5 Conclusion 540 -- References 540 -- 19 Optimization of a Macrocyclic Ghrelin Receptor Agonist (Part II): Development of TZP-102 545 / Hamid R. Hoveyda, Graeme L. Fraser, Eric Marsault, René Gagnon and Mark L. Peterson -- 19.1 Introduction 545 -- 19.2 Advanced AA3 and Tether SAR 548 -- 19.3 Structural Studies 554 -- 19.4 Conclusions 554 -- Acknowledgments 555 -- References 556 -- 20 Solithromycin: Fourth-Generation Macrolide Antibiotic 559 / David Pereira, Sara Wu, Shingai Majuru, Stephen E. Schneider and Lovy Pradeep -- 20.1 Introduction 559 -- 20.2 Structure -Activity Relationship (SAR) of Ketolides and Selection of Solithromycin 559 -- 20.3 Mechanism of Action 564 -- 20.4 Overcoming the Ketek Effect 568 -- 20.5 Manufacture of Solithromycin 569 -- 20.6 Polymorphism 569.
Additional Edition:
Print version: Practical medicinal chemistry with macrocycles. Hoboken, NJ : Wiley, 2017 ISBN 9781119092568
Language:
English
Keywords:
Electronic books.
URL:
https://onlinelibrary.wiley.com/doi/book/10.1002/9781119092599
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