Bioactive Heterocyclic Compound Classes E-Book
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- Herausgeber: Wiley-VCH
- Kategorie: Wissenschaft und neue Technologien
- Sprache: Englisch
The chemistry of heterocycles is an important branch of organic chemistry. This is due to the fact that a large number of natural products, e. g. hormones, antibiotics, vitamins, etc. are composed of heterocyclic structures. Often, these compounds show beneficial properties and are therefore applied as pharmaceuticals to treat diseases or as insecticides, herbicides or fungicides in crop protection. This volume presents important agrochemicals. Each of the 21 chapters covers in a concise manner one class of heterocycles, clearly structured as follows: * Structural formulas of most important examples (market products) *Short background of history or discovery * Typical syntheses of important examples * Mode of action * Characteristic biological activity * Structure-activity relationship * Additional chemistry information (e.g. further transformations, alternative syntheses, metabolic pathways, etc.) * References A valuable one-stop reference source for researchers in academia and industry as well as for graduate students with career aspirations in the agrochemical chemistry.
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Seitenzahl: 392
Veröffentlichungsjahr: 2012
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Table of Contents
Related Titles
Title Page
Copyright
Preface
List of Contributors
Introduction
Chapter 1: The Significance of Heterocycles for Pharmaceuticalsand Agrochemicals
1.1 Introduction
1.2 Heterocycles as Framework of Biologically Active Compounds
1.3 Fine-Tuning the Physicochemical Properties with Heterocycles
1.4 Heterocycles as Prodrugs
1.5 Heterocycles as Peptidomimetics
1.6 Heterocycles as Isosteric Replacement of Functional Groups
1.7 Heterocycles as Isosteric Replacement of Alicyclic Rings
1.8 Heterocycles as Isosteric Replacement of other Heterocyclic Rings
References
Part I: Herbicides
Chapter 2: Triazine Herbicides
2.1 Introduction
2.2 History
2.3 Synthesis
2.4 Mode of Action
2.5 Biological Activity
2.6 Structure–Activity Relationships
References
Chapter 3: Pyrimidinyl and Triazinylsulfonylurea Herbicides
3.1 Introduction
3.2 History
3.3 Synthesis
3.4 Mode of Action
3.5 Biological Activity
3.6 Structure–Activity Relationship
References
Chapter 4: Acetohydroxyacid Synthase Inhibiting Triazolopyrimidine Herbicides
4.1 Introduction
4.2 History
4.3 Synthesis
4.4 Mode of Action
4.5 Biological Activity
4.6 Structure–Activity Relationship
Chapter 5: HPPD-Inhibiting Benzoylpyrazole Herbicides
5.1 Introduction
5.2 History
5.3 Synthesis
5.4 Mode of Action
5.5 Biological Activity
5.6 Structure–Activity Relationship
References
Chapter 6: Pyridyloxyphenoxypropionate Herbicides: Inhibitors of Acetyl-CoA Carboxylase
6.1 Introduction
6.2 History
6.3 Synthesis
6.4 Mode of Action
6.5 Biological Activity
6.6 Structure–Activity Relationships
References
Chapter 7: Imidazolinone Herbicides
7.1 Introduction
7.2 History
7.3 Synthesis
7.4 Mode of Action
7.5 Biological Activity
7.6 Structure–Activity Relationship
References
Chapter 8: Protoporphyrinogen-IX-Oxidase-Inhibiting Uracil Herbicides
8.1 Introduction
8.2 History
8.3 Synthesis
8.4 Mode of Action
8.5 Biological Activity
8.6 Structure–Activity Relationship
References
Part II: Fungicides
Chapter 9: Benzimidazole Fungicides
9.1 Introduction
9.2 History
9.3 Synthesis
9.4 Mode of Action
9.5 Biological Activity
9.6 Structure–Activity Relationship
References
Chapter 10: Morpholine Fungicides for the Treatment of Powdery Mildew
10.1 Introduction
10.2 History
10.3 Synthesis
10.4 Mode of Action
10.5 Biological Activity
10.6 Structure–Activity Relationship
References
Chapter 11: Sterol Biosynthesis Inhibiting Triazole Fungicides
11.1 Introduction
11.2 History
11.3 Synthesis
11.4 Mode of Action
11.5 Biological Activity
11.6 Structure–Activity Relationship
References
Chapter 12: Methionine Biosynthesis-Inhibiting Anilinopyrimidine Fungicides
12.1 Introduction
12.2 History
12.3 Synthesis
12.4 Mode of Action
12.5 Biological Activity
12.6 Structure–Activity Relationship
References
Chapter 13: Phenylpyrrole Fungicides
13.1 Introduction
13.2 History
13.3 Synthesis
13.4 Mode of Action
13.5 Biological Activity
13.6 Structure–Activity Relationship
References
Chapter 14: Broad-Spectrum Fungicidally Active Pyrimidinyldioxy Strobilurins Inhibiting the Respiratory Chain
14.1 Introduction
14.2 History
14.3 Synthesis
14.4 Mode of Action
14.5 Biological Activity
14.6 Structure–Activity Relationship
References
Chapter 15: Pyrazole Carboxamide Fungicides Inhibiting Succinate Dehydrogenase
15.1 Introduction
15.2 History
15.3 Synthesis
15.4 Mode of Action
15.5 Biological Activity
15.6 Structure–Activity Relationships
Acknowledgements
References
Part III: Insecticides
Chapter 16: Avermectin Insecticides and Acaricides
16.1 Introduction
16.2 History
16.3 Synthesis
16.4 Mode of Action
16.5 Biological Activity
16.6 Structure–Activity Relationship
References
Chapter 17: Pyridine and Thiazole-Containing Insecticides as Potent Agonists on Insect Nicotinic Acetylcholine Receptors
17.1 Introduction
17.2 History
17.3 Synthesis
17.4 Mode of Action
17.5 Biological Activity
17.6 Structure–Activity Relationship
References
Chapter 18: Pyrazole and Pyrimidine Acaricides and Insecticides Acting as Inhibitors of Mitochondrial Electron Transport at Complex I
18.1 Introduction
18.2 History
18.3 Synthesis
18.4 Mode of Action
18.5 Biological Activity
18.6 Structure–Activity Relationship
References
Chapter 19: Phenylpyrazole-Containing Fiprole Insecticides
19.1 Introduction
19.2 History
19.3 Synthesis
19.4 Mode of Action
19.5 Biological Activity
19.6 Structure–Activity Relationship
References
Chapter 20: Pyrazolylpyridine Activators of the Insect Ryanodine Receptor
20.1 Introduction
20.2 History
20.3 Synthesis
20.4 Mode of Action
20.5 Biological Activity
20.6 Structure–Activity Relationships
References
Chapter 21: Tetronic Acid Insecticides and Acaricides Inhibiting Acetyl-CoA Carboxylase
21.1 Introduction
21.2 History
21.3 Synthesis
21.4 Mode of Action
21.5 Biological Activity
21.6 Structure–Activity Relationship
References
Index
Related Titles
Jeschke, P., Krämer, W., Schirmer, U.,
Witschel, M. (eds.)
Modern Methods in Crop Protection Research
2012
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ISBN: 978-3-527-33175-8
Dinges, J., Lamberth, C. (eds.)
Bioactive Heterocyclic Compound Classes
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Krämer, W., Schirmer, U., Jeschke, P.,
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Royer, J. (ed.)
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The Editors
Dr. Clemens Lamberth
Syngenta Crop Protection AG
Research Chemistry
Schaffhauserstr. 101
4332 Stein
Schweiz
Dr. Jürgen Dinges
Abbott Laboratories
Global Pharmaceutical R&D
200, Abbott Park Road
Abbott Park, IL 60064-6217
USA
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© 2012 Wiley-VCH Verlag & Co. KGaA, Boschstr. 12, 69469 Weinheim, Germany
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Bioactive Heterocyclic Compound Classes (Pharmaceuticals and Agrochemicals, 2 Volume Set)
ISBN: 978-3-527-32993-9
Print ISBN: 978-3-527-33396-7
ePDF ISBN: 978-3-527-66444-3
ePub ISBN: 978-3-527-66443-6
mobi ISBN: 978-3-527-66442-9
oBook ISBN: 978-3-527-66441-2
Preface
Approximately 70% of all the 2400 pharmaceuticals listed in the online version of “Pharmaceutical Substances” (A. Kleemann et al., Thieme) bear at least one heterocyclic ring; the latest edition of the “Pesticide Manual” (C. D. S. Tomlin, BCPC) contains a similar percentage of heterocyclic agrochemicals among its about 900 entries. This vast number of known pharmaceuticals and agrochemicals makes the field of commercialized active ingredients an unmanageable jungle. Only specialists are able to understand the connectivities of these active ingredients, many of which are heterocycles.
Therefore, we decided to put this book together, which tries to show the relationship of those heterocyclic active ingredients, which belong together, forming a biologically active heterocylic chemistry class. According to our definition, such a heterocyclic family is built from at least three compounds that fulfill the following conditions: (i) same heterocyclic scaffold, (ii) same mode of action, and (iii) similar substitution pattern.
Although the strength of this concept is that for the first time the members of the most important heterocyclic active ingredient families, their historical background, chemical syntheses, biochemical modes of action, and biological activities are discussed in detail, there are also some limitations. For instance, there are some heterocyclic families of drugs or crop protection agents, such as the analgesic COX-2 inhibitors celecoxib, valdecoxib, and rofecoxib or the dicarboxamide fungicides vinclozolin, iprodione, and procymidone, which are closely related by structure and possess the same mode of action, but bear different heterocyclic scaffolds and therefore could not be considered.
We would like to thank the authors of the 40 chapters of this book, all of them experts in their field, for spending their scarce time summarizing their area of interest. They all agreed to write the chapters according to the same outline: (i) introduction, (ii) history, (iii) synthesis, (iv) mode of action, and (v) structure–activity relationship. Only the agrochemical chapters possess an additional section “biological activity,” mainly describing the target spectrum of the active ingredients. This book would definitely not exist without your engagement!
Furthermore, we also would like to thank Anne Brennführer and Stefanie Volk of Wiley-VCH, who from the beginning guided us very efficiently through all different phases of this exciting project.
The introductory chapter about “The significance of heterocycles for pharmaceuticals and agrochemicals” tries to explain the different roles of heterocyclic scaffolds in active ingredients, e.g. as framework of biologically active substances, as prodrugs, as tool for fine-tuning the physicochemical properties, as isosteric replacements of functional groups, alicyclic rings or other heterocyclic rings. As this is demonstrated at the hand of many prominent and characteristical examples of pharmaceuticals as well as of agrochemicals, also pointing out the many similarities, but also some differences between the two big classes of active ingredients, we decided to put this chapter in front of both volumes.
Although currently living in two different continents, both of us enjoyed exactly the same excellent education, a Ph.D. in organic chemistry from the Technical University at Darmstadt, Germany, and a subsequent postdoctoral fellowship at the chemistry department of the University of California at Berkeley. We are very grateful to our teachers, mentors, and research advisors at both universities, who built the foundation for our successful work in the research departments of the agrochemical and pharmaceutical industry.
Finally, we are deeply indebted to our wives Annette and Petra, who continuously supported us, as always, and tolerated that we spent many hours of our spare time, which should have belonged to our families, working on this book. You really made this possible!
Clemens Lamberth
Switzerland
Jürgen Dinges
USA
List of Contributors
Introduction
1
The Significance of Heterocycles for Pharmaceuticalsand Agrochemicals*
Clemens Lamberth and Jürgen Dinges
1.1 Introduction
Heterocycles, their preparation, transformation, and properties, are undoubtedly a cornerstone of organic chemistry. Several books not only on heterocyclic chemistry [1–6] but also on some special aspects, such as heterocyclic name reactions [7], heterocyclic palladium-catalyzed reactions [8], heterocyclic carbene complexes [9], and fluorinated heterocycles [10], have been published recently.
Approximately more than 70% of all pharmaceuticals and agrochemicals bear at least one heterocyclic ring. In addition, some of the biggest commercial products to date, such as the blockbuster blood cholesterol reducer atorvastatin (Lipitor®, 1) [11] for the treatment of dyslipidemia and the prevention of cardiovascular diseases and the broad-spectrum fungicide azoxystrobin (Amistar, ) [12], currently applied against diseases of more than 100 different crops in more than 100 different countries, belong to this huge heterocyclic group of active ingredients ().
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