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| 008 | 190918s2017 nju ob 001 0 eng | ||
| 010 | _a2017-024680 | ||
| 020 |
_a9781119092582 _q(electronic bk.) |
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| 020 |
_a1119092582 _q(electronic bk.) |
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| 020 |
_a9781119092599 _q(electronic bk. : oBook) |
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| 020 |
_a1119092590 _q(electronic bk. : oBook) |
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| 020 | _z9781119092902 | ||
| 020 | _z1119092906 | ||
| 020 | _z9781119092568 (hardback) | ||
| 035 | _a(OCoLC)987890450 | ||
| 035 | _a(OCoLC)ocn987890450 | ||
| 039 | 9 |
_a201911041629 _bros _y09-18-2019 _zhafiz _wUKM UBCM Wiley MARC (363 titles).mrc _x326 |
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_aDLC _beng _erda _cDLC _dOCLCO _dOCLCF _dNST _dIDEBK _dOCLCQ _dMERUC _dUIU _dDG1 _dUPM |
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| 049 | _aMAIN | ||
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| 072 | 7 |
_aMED _x071000 _2bisacsh |
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_a615.1/9 _223 |
| 245 | 0 | 0 |
_aPractical medicinal chemistry with macrocycles : _bdesign, synthesis, and case studies / _cedited by Eric Marsault, University of Sherbrooke, Quebec, Canada, Mark L. Peterson, Quebec, Canada. |
| 263 | _a1708 | ||
| 264 | 1 |
_aHoboken, NJ : _bWiley, _c2017. |
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| 300 | _a1 online resource. | ||
| 336 |
_atext _btxt _2rdacontent |
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| 337 |
_acomputer _bn _2rdamedia |
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| 338 |
_aonline resource _bnc _2rdacarrier |
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| 504 | _aIncludes bibliographical references and index. | ||
| 505 | 0 | _aForeword 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 / É<i>ric Biron, Simon Vezina<i>?]<i>Dawod and Fran<i>ç<i>ois B<i>é<i>dard -- 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 β?]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<i>?]<i>Catherine B<i>é<i>dard, Myl<i>è<i>ne de L<i>é<i>s<i>é<i>leuc, Micha<i>ë<i>l 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 Ch<i>á<i>vez Morej<i>ó<i>n -- 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, Ren<i>é<i> Gagnon and Mark L. | |
| 505 | 0 | _aPeterson -- 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 -- 20.7 Pharmaceutical De | |
| 588 | _aDescription based on print version record and CIP data provided by publisher; resource not viewed. | ||
| 590 |
_aJohn Wiley and Sons _bWiley Online Library All Obooks |
||
| 650 | 0 | _aDrug development. | |
| 650 | 0 | _aPharmaceutical chemistry. | |
| 650 | 7 |
_aDrug development. _2fast _0(OCoLC)fst00898670 |
|
| 650 | 7 |
_aPharmaceutical chemistry. _2fast _0(OCoLC)fst01060115 |
|
| 650 | 7 |
_aMEDICAL / Pharmacology _2bisacsh |
|
| 655 | 4 | _aElectronic books. | |
| 700 | 1 |
_aMarsault, Eric, _d1971- _eeditor. |
|
| 700 | 1 |
_aPeterson, Mark L., _d1958- _eeditor. |
|
| 773 | 0 | _tWiley e-books | |
| 776 | 0 | 8 |
_iPrint version: _tPractical medicinal chemistry with macrocycles _dHoboken, NJ : Wiley, 2017 _z9781119092568 _w(DLC) 2017011916 |
| 856 | 4 | 0 |
_uhttps://eresourcesptsl.ukm.remotexs.co/user/login?url=https://doi.org/10.1002/9781119092599 _zWiley Online Library |
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