Peptidomimetics in organic and medicinal chemistry / Andrea Trabocchi and Antonio Guarna.

Format:

Book

Author/Creator:

Guarna, Antonio, author.

Language:

English

Subjects (All):

Peptide drugs.

Proteins--Therapeutic use.

Proteins.

Drugs--Design.

Drugs.

Physical Description:

1 online resource (320 p.)

Edition:

1st ed.

Place of Publication:

Chichester, West Sussex, United Kingdom : John Wiley & Sons, 2014.

Language Note:

English

Summary:

"A peptidomimetic is a small protein-like chain designed to mimic a peptide with adjusted molecular properties such as enhanced stability or biological activity. It is a very powerful approach for the generation of small-molecule-based drugs as enzyme inhibitors or receptor ligands.Peptidomimetics in Organic and Medicinal Chemistry outlines the concepts and synthetic strategies underlying the building of bioactive compounds of a peptidomimetic nature. Topics covered include the chemistry of unnatural amino acids, peptide- and scaffold-based peptidomimetics, amino acid-side chain isosteres, backbone isosteres, dipeptide isosteres, beta-turn peptidomimetics, proline-mimetics as turn inducers, cyclic scaffolds, amino acid surrogates, and scaffolds for combinatorial chemistry of peptidomimetics. Case studies in the hit-to-lead process, such as the development of integrin ligands and thrombin inhibitors, illustrate the successful application of peptidomimetics in drug discovery"-- Provided by publisher.

"Peptidomimetics in Organic and Medicinal Chemistry outlines the concepts and synthetic strategies underlying the building of bioactive compounds of a peptidomimetic nature"-- Provided by publisher.

Contents:

Cover; Title Page; Copyright; Contents; Preface; Abbreviations; Part I The Basics of Peptidomimetics; Chapter 1 The Basics of Peptidomimetics; 1.1 Introduction; 1.2 Definition and Classification; 1.3 Strategic Approaches to Peptidomimetic Design; 1.3.1 Modification of Amino Acids; 1.3.2 Compounds with Global Restrictions; 1.3.3 Molecular Scaffolds Mimicking the Peptidic Backbone; 1.4 Successful Examples of Peptidomimetic Drugs; 1.4.1 ACE Inhibitors; 1.4.2 Thrombin Inhibitors; 1.5 Conclusion; References; Chapter 2 Synthetic Approaches towards Peptidomimetic Design; 2.1 Introduction

2.2 Local Modifications2.2.1 Single Amino Acid Modifications; 2.2.2 Dipeptide Isosteres; 2.2.3 Retro-inverso Peptides; 2.2.4 N-Methylation of Peptides; 2.2.5 Azapeptides; 2.2.6 Peptoids; 2.3 Global Restrictions through Cyclic Peptidomimetics; 2.4 Peptidomimetic Scaffolds; 2.5 Conclusions; References; Part II Synthetic Methods and Molecules; Chapter 3 Peptidomimetic Bioisosteres; 3.1 Introduction; 3.2 Peptide Bond Isosteres; 3.2.1 Thioamides; 3.2.2 Esters; 3.2.3 Alkenes and Fluoroalkenes; 3.2.4 Transition-State Isosteres; 3.3 Side-Chain Isosteres

3.3.1 Guanidine Isosteres in Arginine Peptidomimetics3.3.2 Isosteres of Aspartic Acid and Glutamic Acid; 3.3.3 Tethered α-Amino Acids: Constraining the x-Space; 3.4 Dipeptide Isosteres; 3.4.1 δ-Amino Acids; 3.5 Tripeptide Isosteres; 3.6 Conclusion; References; Chapter 4 Solid-Phase Synthesis and Combinatorial Approaches to Peptidomimetics; 4.1 Introduction; 4.2 Solid-Phase Synthesis of Peptidomimetics; 4.2.1 Scaffolds from α-Amino Acids; 4.2.2 Scaffolds from Amino Aldehyde Intermediates; 4.2.3 Pyrrolidine-Containing Scaffolds; 4.3 Conclusion; References

Chapter 5 Click Chemistry: The Triazole Ring as a Privileged Peptidomimetic Scaffold5.1 Introduction; 5.1.1 CuAAC Reaction; 5.1.2 Triazole Ring as a Peptidomimetic Isostere; 5.2 Triazole-Containing Peptidomimetics Elaborated through `Click Chemistry'; 5.2.1 Macrocycles; 5.2.2 Oligomers and Foldamers; 5.3 Relevant Applications in Drug Discovery; 5.3.1 AChE Inhibitors; 5.3.2 HIV Protease Inhibitors; 5.3.3 MMP Inhibitors; 5.3.4 Integrin Ligands; 5.4 Conclusions; Acknowledgements; References; Chapter 6 Peptoids; 6.1 Introduction and Basics of Peptoids; 6.2 Synthetic Methods

6.3 Macrocyclic Peptoids6.4 Conformational Analysis of Folded Peptoids; 6.5 Application of Peptoids as Antimicrobial Peptidomimetics; 6.6 Conclusions; References; Chapter 7 Sugar Amino Acids; 7.1 Introduction; 7.2 α-SAAs; 7.2.1 Furanoid α-SAAs; 7.2.2 Pyranoid α-SAAs; 7.3 β-SAAs; 7.3.1 Furanoid β-SAAs; 7.3.2 Pyranoid β-SAAs; 7.4 r-SAAs1; 7.5 δ-SAAs; 7.5.1 Furanoid δ-SAAs; 7.5.2 Pyranoid δ-SAAs; 7.6 Representative Applications in Medicinal Chemistry; 7.7 Conclusions; References; Chapter 8 Cyclic α-Amino Acids as Proline Mimetics; 8.1 Introduction; 8.2 Cyclic α-Amino Acids

8.2.1 3-Substituted Proline Derivatives

Notes:

Description based upon print version of record.

Includes bibliographical references and index.

Description based on print version record.

ISBN:

9781118683149

1118683145

9781118683033

111868303X

9781118683842

1118683846

OCLC:

874322807