Signposts to chiral drugs: organic synthesis in action/ (Record no. 185221)
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| 000 -LEADER | |
|---|---|
| fixed length control field | 00336nam a2200133Ia 4500 |
| 020 ## - INTERNATIONAL STANDARD BOOK NUMBER | |
| International Standard Book Number | 9783034801249 |
| 040 ## - CATALOGING SOURCE | |
| Transcribing agency | CUS |
| 082 ## - DEWEY DECIMAL CLASSIFICATION NUMBER | |
| Classification number | 540.5 |
| Item number | SUN/ |
| 100 ## - MAIN ENTRY--PERSONAL NAME | |
| Personal name | Sunjic, Vitomir |
| 245 #0 - TITLE STATEMENT | |
| Title | Signposts to chiral drugs: organic synthesis in action/ |
| Statement of responsibility, etc. | Vitomir Sunjic, Michael J. Parnham |
| 260 ## - PUBLICATION, DISTRIBUTION, ETC. (IMPRINT) | |
| Place of publication, distribution, etc. | New York : |
| Name of publisher, distributor, etc. | Springre, |
| Date of publication, distribution, etc. | 2011. |
| 300 ## - PHYSICAL DESCRIPTION | |
| Extent | 252p. : |
| Dimensions | 24cm. |
| 504 ## - BIBLIOGRAPHY, ETC. NOTE | |
| Bibliography, etc | Includes index. |
| 505 ## - FORMATTED CONTENTS NOTE | |
| Formatted contents note | 1 Organic Synthesis in Drug Discovery and Development 1<br/><br/>1.1 Introduction 1<br/><br/>1.2 Synthetic Organic Chemistry in Pharmaceutical R&D 2<br/><br/>1.3 New Concepts in the Drug Discovery Process 5<br/><br/>1.3.1 The Impact of Natural Products on Modern Drug Discovery 6<br/><br/>1.3.2 Biologically Orientated Synthesis in Drug Discovery 8<br/><br/>1.3.3 Incorporation of Genomics and DNA-templated Synthesis into Drug Discovery 9<br/><br/>1.4 Conclusion 11<br/><br/>Reference 11<br/><br/>2 Aliskiren Fumarate 13<br/><br/>2.1 Introduction 13<br/><br/>2.2 Renin and the Mechanism of Aliskiren 14<br/><br/>2.3 Structural Characteristics and Synthetic Approaches to Aliskiren 16<br/><br/>2.3.1 Strategy Based on Visual Imagery, Starting from Nature's Chiral Pool: A Dali-Like Presentation of Objects 18<br/><br/>2.3.2 Fine-Tuning of the Chiral Ligand for the Rh Complex: Hydrogenation of the Selected Substrate with Extreme Enantioselectivities 21<br/><br/>2.4 Conclusion 26<br/><br/>References 26<br/><br/>3 (R)-K-13675 29<br/><br/>3.1 Introduction 29<br/><br/>3.2 Peroxisome Proliferator-Activated Receptor α Agonists 29<br/><br/>3.2.1 β-Phenylpropionic Acids 30<br/><br/>3.2.2 α-Alkoxy-β-Arylprionic Acids 31<br/><br/>3.2.3 α-Aryloxy-β-Phenyl Propionic Acids 33<br/><br/>3.2.4 Oxybenzoylglycine Derivatives 34<br/><br/>3.3 Non-hydrolytic Anomalous Lactone Ring-Opening 35<br/><br/>3.4 Mitsunobu Reaction in the Ether Bond Formation 38<br/><br/>3.5 Conclusion 42<br/><br/>References 42<br/><br/>4 Sitagliptin Phosphate Monohydrate 45<br/><br/>4.1 Introduction 45<br/><br/>4.2 Endogenous Glucoregulatory Peptide Hormones and Dipeptidoyl Peptides IV (DPP4) Inhibitors 46<br/><br/>4.3 Synthesis with C-acyl Meldrum's Acid as the N-Acylating Agent 47<br/><br/>4.4 Highly Enantioselective Hydrogenation of Unprotected β-Enamino Amides and the Use of Josiphos-Ligands 50<br/><br/>4.5 Ammonium Chloride, an Effective Promoter of Catalytic Enantioselective Hydrogenation 52<br/><br/>4.6 Conclusion 53<br/><br/>References 53<br/><br/>5 Biaryl Units in Valsartan and Vancomycin 55<br/><br/>5.1 Introduction 55<br/><br/>5.2 Angiotension AT Receptor, a G-Protein-Coupled Receptor 56<br/><br/>5.3 Cu-Promoted Catalytic Decarboxylative Biaryl Synthesis, a Biomimetic Type Aerobic Decarboxylation 59<br/><br/>5.4 Streiselective Approach to the Axially Chiral Biaryl System; the Case of Vancomycin 63<br/><br/>5.5 Conclusion 67<br/><br/>References 67<br/><br/>6 3-Amino-1,4-Bezodiazepines 69<br/><br/>6.1 Introduction 69<br/><br/>6.2 3-Amino-1,4-Benzodiazepine Derivatives as γ-Secretase Inhibitors 70<br/><br/>6.3 Configurational Stability: Racemization and Enantiomerization 71<br/><br/>6.4 Crystallization Induced Asymmetric Transformation 74<br/><br/>6.5 Asymmetric Ireland-Claisen Rearrangement 74<br/><br/>6.6 Hydrobroation of the Terminal C=C Bond: Anti-Markovnikov Hydratation 76<br/><br/>6.7 Crustallization-Induced Asummetric Transformation in the Synthesis of L-768,673 79<br/><br/>6.8 Conclusion 81<br/><br/>References 81<br/><br/>7 Sertraline 83<br/><br/>7.1 Introduction 83<br/><br/>7.2 Synaptosomal Serotonin Uptake and Its Selective Inhibitors (SSRI) 84<br/><br/>7.3 Action of Sertraline and Its Protein Target 85<br/><br/>7.4 General Synthetic Route 86<br/><br/>7.5 Stereoselective Reduction of Ketones and Imines Under Kinetic and Thermodynamic Control 87<br/><br/>7.5.1 Diastereoselectivity of Hudrogenation of rac-tetralone-Methylimine: The Old (MeNH2/TiCl4/Toluence) Method Is Improved by Using MeNH2/EtOH-Pd/CaCO3, 60-65°C in a Telescoped Process 87<br/><br/>7.5.2 Kinetic Resolution of Racemic Methylamine: Hydrosilylation by (R,R)-(EBTHI)TiF2/PhSiH3 Catalytic System 88<br/><br/>7.5.3 Catalytic Epimerization of the Trans- to the Cis-Isomer of Sertralilne 90<br/><br/>7.5.4 Stereoselective Reduction of Tetralone by Chiral Diphenyloxazaborolidine 91<br/><br/>7.6 Desymmetrization of Oxabenzonorbornadiene, Suzuki Coupling of Arylboronic Acids and Vinyl Halides 92<br/><br/>7.7 Pd-Catalyzed (Tsuji-Trost) Coupling of Arylboronic Acids and Allylic Esters 94<br/><br/>7.8 Simulated Moving Bed in the Commercial Production of Sertaline 97<br/><br/>7.9 Conclusion 101<br/><br/>References 101<br/><br/>8 1,2-Dihydroquinolines 103<br/><br/>8.1 Introduction 103<br/><br/>8.2 Glucocorticoid Receptor 103<br/><br/>8.3 Asymmetric Organocatalysis: Introducing a Thiourea Catalyst for the Petasis Reaction 105<br/><br/>8.3.1 General Consideration of the Petasis Reaction 106<br/><br/>8.3.2 Catalytic, Enantioselective Petasis Reaction 109<br/><br/>8.4 Multi-component Reactions: General Concept and Examples 112<br/><br/>8.4.1 General Concept of Multi-component Reactions 112<br/><br/>8.4.2 Efficient, Isocyanide-Based Ugi Multi-component Reactions 113<br/><br/>References 115<br/><br/>9 (-) -Menthol 117<br/><br/>9.1 Introduction 117<br/><br/>9.2 Natural Sources and First Technological Production of (-) -Menthol 118<br/><br/>9.3 Enantioselective Allylic Amine-Enamine-Imine Rearrangement, Catalysed by Rh(I)-(-) -BINAP Complex 119<br/><br/>9.4 Production Scale Synthesis of Both Enantiomers 122<br/><br/>9.5 Conclusion 123<br/><br/>References 123<br/><br/>10 Fexofenadine Hydrochloride 125<br/><br/>10.1 Introduction 125<br/><br/>10.2 Histamine Receptors as Biological Targets for Anti-allergy Drugs 126<br/><br/>10.3 Absolute Configuration and "Racemic Switch" 127<br/><br/>10.4.1 ZnBr2-Catalyzed Rearrangement of α-Haloketones to Terminal Carboxylic Acids 131<br/><br/>10.4.2 Microbial Oxidation of Non-activated C-H Bond 135<br/><br/>10.4.3 Bioisosterism: Silicon Switch of Fexofenadine to Sila-Fexofenadine 137<br/><br/>10.5 Conclusion 139<br/><br/>References 139<br/><br/>11 Montelukast Sodium 141<br/><br/>11.1 Introduction 141<br/><br/>11.2 Leukotriene D4 Receptor (LTD4), CysLT-1 Receptor Antagonists 142<br/><br/>11.3 Hydroboration of Ketones with Boranes from α-Pinenes and the Non-linear Effect in Asymmetric Reactions 144<br/><br/>11.4 Ru(II) Catalyzed Enantioselective Hydrogen Transfer 148<br/><br/>11.5 Biocatalytic Reduction with Ketoreductase KRED (KetoREDuctase) 150<br/><br/>11.6 CeCl3-THF Solvate as a Promoter of the Grignard Reaction: Phase Transfer Catalysis 150<br/><br/>11.7 Conclusion 152<br/><br/>References 153<br/><br/>12 Thilactone Peptides as Antibacterial Peptidomimetics 155<br/><br/>12.1 Introduction 155<br/><br/>12.2 Virulence and Quououm-Sensing System of Stapyylococcus aureus 156<br/><br/>12.3 Development of Chemical Ligation in Peptide Synthesis 158<br/><br/>12.4 Development of Native Chemical Ligation: Chemoselectivity in Peptide Synthesis 160<br/><br/>12.5 Development of NCL in Thiolactone Petide Synthesis 163<br/><br/>12.6 Conclusion 167<br/><br/>References 167<br/><br/>13 Efavirenz 169<br/><br/>13.1 Introduction 169<br/><br/>13.2 HIV-1 Reverse Transcriptase Inhibitors 170<br/><br/>13.2.1 Setric Interactions at the Active Site 171<br/><br/>13.3 Asymmetric Addition of Alkyne Anion to C=O Bond with Formation of Chiral Li+ Aggregates 173<br/><br/>13.3.1 Mechanism of the Chirality Transfer 173<br/><br/>13.3.2 Equilibration of Lithium Aggregates and the Effect of Their Relative Stability on Enantioselectivity 175<br/><br/>13.4 Scale-up of Alkynylation Promoted by the Use fo Et2Zn 176<br/><br/>13.5 Conclusion 177<br/><br/>References 177<br/><br/>14 Paclitaxel 179<br/><br/>14.1 Introduction 179<br/><br/>14.2 Disturbed Dynamics of Cellular Microtubules by Binding to β-Tubulin 180<br/><br/>14.3 Three Selected Synthetic Transformations on the Pathway to Paclitaxel 181<br/><br/>14.3.1 Intramolecular Heck Reaction on the Synthetic Route to Baccatin III 182<br/><br/>14.3.2 Trifunctional Catalyst for Biomimetic Synthesis of Chiral Diols: Synthesis of the Paclitaxel Side-Chain 185<br/><br/>14.3.3 Zr-Complex Catalysis in the Reductive N-deacylation of Taxanes to the Primary Amine, the Key Precursor of Paclitaxel 192<br/><br/>14.4 Conclusion 194<br/><br/>References 194<br/><br/>15 Neoglycoconjugate 197<br/><br/>15.1 Introduction 197<br/><br/>15.2 Human, α-1,3-Fucosyltransferase IV (Fuc-T) 198<br/><br/>15.3 Click Chemistry: Energetically Preferred Reactions 200<br/><br/>15.4 Target-Guided Synthesis or Freeze-Frame Click Chemistry 202<br/><br/>15.5 Application of Click Chemistry to the Synthesis of Neoglycoconjugate 1 205<br/><br/>15.6 Conclusion 207<br/><br/>References 207<br/><br/>16 12-Aza-Epothilones 209<br/><br/>16.1 Introduction 209<br/><br/>16.2 Epothilones: Mechanism of Action and Structure-Activity Relationships 210<br/><br/>16.3 Extensive vs. Peripheral Structure Modifications of Natural Products 212<br/><br/>16.4 Ring Closure Metathesis: An Efficient Approach to Macrocyclic "Non-natural Natural Products" 213<br/><br/>16.5 Diimide Reduction of the Allylic C=C Bond 220<br/><br/>16.6 Conclusion 222<br/><br/>References 222<br/><br/>Synthetic Methods and Concepts Discussed in the Chapters 225<br/> |
| 650 ## - SUBJECT | |
| Keyword | Drug Discovery -- methods. |
| 650 ## - SUBJECT | |
| Keyword | Pharmaceutical Preparations -- chemistry. |
| 650 ## - SUBJECT | |
| Keyword | Structure-Activity Relationship. |
| 700 ## - ADDED ENTRY--PERSONAL NAME | |
| Personal name | Parnham, Michael J. |
| 942 ## - ADDED ENTRY ELEMENTS (KOHA) | |
| Koha item type | General Books |
| Withdrawn status | Lost status | Damaged status | Not for loan | Home library | Current library | Shelving location | Date acquired | Full call number | Accession number | Date last seen | Koha item type |
|---|---|---|---|---|---|---|---|---|---|---|---|
| Central Library, Sikkim University | Central Library, Sikkim University | General Book Section | 29/08/2016 | 540.5 SUN/ | P40233 | 29/08/2016 | General Books |