Development of Methods for the Synthesis of Natural Product-like Macrocycles PDF Download
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Author: Mark John Laurence Dow
Publisher:
ISBN:
Category :
Languages : en
Pages : 538
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Book Description
This thesis describes a modular diversity-oriented synthesis approach, which exploited a 'build→couple→couple→pair' reaction sequence, to generate a library of natural product-like macrocycles. The use of a fluorous-tagged building block allowed the expedient purification of the substrates between the 'couple→couple' stages of the sequence. Building blocks were iteratively linked onto the fluorous tagged building block to give linear substrates bearing two terminal alkenes. These substrates were subjected to ring-closing metathesis to yield diverse macrocyclic scaffolds. Subsequent, deprotection and diversification steps yielded natural product-like macrocycles. Using this approach, over 13 macrocyclic scaffolds were prepared which, in turn, after diversification, yielded over 55 diverse macrocycles, each with unique scaffolds. In addition this project also saw the synthesis of the corresponding linear compounds. Chapter 1 discusses the importance of macrocycles in nature, how this class of molecules have been poorly explored and methods that have been used to explore chemical space. Chapter 2 describes the synthesis of the building blocks and the proposed method to prepare the library of diverse macrocycles. Chapter 3 explores the reactivity of the building blocks and developments required to improve the efficiency of the library synthesis. Chapter 4 describes the final library synthesis from building blocks to final compounds. This work aims to prepare compounds with potential bioactivity; however, the biological evaluation of the compounds is beyond the remit of the study.
Author: Mark John Laurence Dow
Publisher:
ISBN:
Category :
Languages : en
Pages : 538
Get Book Here
Book Description
This thesis describes a modular diversity-oriented synthesis approach, which exploited a 'build→couple→couple→pair' reaction sequence, to generate a library of natural product-like macrocycles. The use of a fluorous-tagged building block allowed the expedient purification of the substrates between the 'couple→couple' stages of the sequence. Building blocks were iteratively linked onto the fluorous tagged building block to give linear substrates bearing two terminal alkenes. These substrates were subjected to ring-closing metathesis to yield diverse macrocyclic scaffolds. Subsequent, deprotection and diversification steps yielded natural product-like macrocycles. Using this approach, over 13 macrocyclic scaffolds were prepared which, in turn, after diversification, yielded over 55 diverse macrocycles, each with unique scaffolds. In addition this project also saw the synthesis of the corresponding linear compounds. Chapter 1 discusses the importance of macrocycles in nature, how this class of molecules have been poorly explored and methods that have been used to explore chemical space. Chapter 2 describes the synthesis of the building blocks and the proposed method to prepare the library of diverse macrocycles. Chapter 3 explores the reactivity of the building blocks and developments required to improve the efficiency of the library synthesis. Chapter 4 describes the final library synthesis from building blocks to final compounds. This work aims to prepare compounds with potential bioactivity; however, the biological evaluation of the compounds is beyond the remit of the study.
Author: Eric Marsault
Publisher: John Wiley & Sons
ISBN: 1119092566
Category : Science
Languages : en
Pages : 617
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Book Description
Including case studies of macrocyclic marketed drugs and macrocycles in drug development, this book helps medicinal chemists deal with the synthetic and conceptual challenges of macrocycles in drug discovery efforts. Provides needed background to build a program in macrocycle drug discovery –design criteria, macrocycle profiles, applications, and limitations Features chapters contributed from leading international figures involved in macrocyclic drug discovery efforts Covers design criteria, typical profile of current macrocycles, applications, and limitations
Author: Pei-Qiang Huang
Publisher: John Wiley & Sons
ISBN: 1118940210
Category : Science
Languages : en
Pages : 512
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Book Description
Uniting the key organic topics of total synthesis and efficient synthetic methodologies, this book clearly overviews synthetic strategies and tactics applied in total synthesis, demonstrating how the total synthesis of natural products enables scientific and drug discovery. • Focuses on efficiency, a fundamental and important issue in natural products synthesis that makes natural product synthesis a powerful tool in biological and pharmaceutical science • Describes new methods like organocatalysis, multicomponent and cascade reactions, and biomimetic synthesis • Appeals to graduate students with two sections at the end of each chapter illustrating key reactions, strategies, tactics, and concepts; and good but unfinished total synthesis (synthesis of core structure) before the last section • Compiles examples of solid phase synthesis and continuing flow chemistry-based total synthesis which are very relevant and attractive to industry R&D professionals
Author: Sasadhar Majhi
Publisher: World Scientific
ISBN: 9811268703
Category : Science
Languages : en
Pages : 469
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Book Description
Modern Sustainable Techniques in Total Synthesis of Bioactive Natural Products comprises five parts for green tools, such as ultrasonic waves, microwave heating, visible-light photochemistry, organic electrochemistry, and flow chemistry, along with 72 chapters for each bioactive molecule of natural origin. Each chapter explores the natural source, structure, systematic name, structural features, compound class, biological activity, conventional approaches for their chemical synthesis, and demerit(s) of conventional approaches (where applicable). Finally, critical features of total synthesis using modern sustainable techniques, including reaction types, synthetic strategy, and synthetic route utilizing modern sustainable tools for each bioactive natural product and secondary metabolites, are discussed brilliantly. The spectrum of application of total synthesis of bioactive natural products using modern sustainable techniques may promote the development of more eco-friendly synthetic processes so that the next generations can live on this planet with a minimum energy requirement for chemical reactions with the least pollution.
Author: Matthew B. Coppock
Publisher: Humana
ISBN: 9781071616888
Category : Technology & Engineering
Languages : en
Pages : 469
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Book Description
This volume explores the latest techniques and strategies used to study the field of peptide macrocycles. The chapters in this book ae organized into four parts: macrocycles synthesis, combinational library synthesis and screening, macrocycle characterization, and unique applications. Part One looks at a variety of peptide cyclization methodologies, and Part Two describes methods for the creation of peptide macrocycles libraries and their subsequent screening against biological targets of interest. Part Three discusses the study and characterization of peptide macrocycle-target interactions, and Part Four introduces unique applications for peptide macrocycles, from higher-order structure formation to post-synthetic functional modifications. Written in the highly successful Methods in Molecular Biology series format, chapters include introductions to their respective topics, lists of the necessary materials and reagents, step-by-step, readily reproducible laboratory protocols, and tips on troubleshooting and avoiding known pitfalls. Cutting-edge and comprehensive, Peptide Macrocycles: Methods and Protocols is a valuable resource for both novice and expert researchers looking to learn more about this developing field.
Author: Chris Lorenc
Publisher:
ISBN:
Category :
Languages : en
Pages : 0
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Book Description
Author: Janine Cossy
Publisher: John Wiley & Sons
ISBN: 3527642080
Category : Science
Languages : en
Pages : 413
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Book Description
Emphasizing the impact of metathesis in natural product synthesis through the different types of key reactions, this is a comprehensive view of a hot topic. Written by top international authors, this ready reference is clearly structured and packed with important information, including representative experimental procedures for practical applications. A real must-have for anyone working in natural product synthesis.
Author: Tomas Hudlicky
Publisher: Wiley-VCH
ISBN:
Category : Science
Languages : en
Pages : 1032
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Book Description
This two-colored textbook presents not only synthetic ways to design organic compounds, it also contains a compilation of the most important total synthesis of the last 50 years with a comparative view of multiple designs for the same targets. It explains different tactics and strategies, making it easy to apply to many problems, regardless of the synthetic question in hand. Following a historical view of the evolution of synthesis, the book goes on to look at principles and issues impacting synthesis and design as well as principles and issues of methods. The sections on comparative design cover classics in terpenes and alkaloid synthesis, while a further section covers such miscellaneous syntheses as Maytansine, Palytoxin, Brevetoxin B and Indinavir. The whole is rounded off with a look at future perspectives and, what makes this textbook extraordinairy, with personal recollections of the chemists, who synthesized these fascinating compounds. With its attractive layout highlighting key parts and tactics using a second color, this is a useful tool for organic chemists, lecturers and students in chemistry, as well as those working in the chemical industry. "I think, as will many organic chemists, that the Hudlicky book will be the Bible of synthetic organic chemistry, the past, the present and the future. A hallmark publication." (Victor Snieckus)
Author: Andrea Basso
Publisher: Frontiers Media SA
ISBN: 2889457885
Category :
Languages : en
Pages : 150
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Book Description
Has the concept of Diversity Oriented Synthesis remained unchanged over these two decades, or do we observe improvements or deviations from the original guidelines drawn by the pioneers? The aim of this Research Topic is to collect contributions on the state-of-the-art and progress of Diversity Oriented Synthesis, and to foresee its shape in the next decade.
Author: Ali Tavassoli
Publisher: Royal Society of Chemistry
ISBN: 178801569X
Category : Science
Languages : en
Pages : 357
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Book Description
Protein-protein interactions (PPI) are at the heart of the majority of cellular processes, and are frequently dysregulated or usurped in disease. Given this central role, the inhibition of PPIs has been of significant interest as a means of treating a wide variety of diseases. However, there are inherent challenges in developing molecules capable of disrupting the relatively featureless and large interfacial areas involved. Despite this, there have been a number of successes in this field in recent years using both traditional drug discovery approaches and innovative, interdisciplinary strategies using novel chemical scaffolds. This book comprehensively covers the various aspects of PPI inhibition, encompassing small molecules, peptidomimetics, cyclic peptides, stapled peptides and macrocycles. Illustrated throughout with successful case studies, this book provides a holistic, cutting-edge view of the subject area and is ideal for chemical biologists and medicinal chemists interested in developing PPI inhibitors.
