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Bioorganic and Medicinal Chemistry of Fluorine. Edited by Jean-Pierre Bgu and Danile Bonnet-Delpon

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Angewandte
Books
Chemie
Stereoselective Polymerization
with Single-Site Catalysts
Edited by Lisa S.
Baugh and Jo Ann
M. Canich. CRC/
Taylor & Francis,
Boca Raton 2007.
712 pp., hardcover
$ 249.95.—ISBN
978-1-57444-579-4
Although I winced at the title (many of
the catalysts described are two-site catalysts rather than single-site, as pointed
out in several chapters), the book is a
good reference text covering all important aspects of stereoselective polymerization, not only of the classic olefins
and diolefins, but also including that of
acetylene, CO copolymers, acrylates,
epoxides, and lactides. Several chapters,
especially those in Section II (polypropylene: application of tacticity), are a
pleasure to read.
However, I found that two important aspects are missing from the book:
the industrial dimension of homogeneous catalysis for stereoregular polypropylene, and the influence of tacticity on
(semicrystalline) copolymer properties
(with the notable exception of the
chapter on ethylene–propylene rubbers), despite the existence of a large
bulk of literature, especially on the
latter subject.
Concerning the first point, almost 10
years of intensive and successful industrial development of metallocenes and
post-metallocenes for the production of
isotactic polypropylene (i-PP) and propylene-based copolymers has apparently gone unnoticed. With only a
Angew. Chem. Int. Ed. 2008, 47, 8155 – 8156
dozen references later than 2000, the
first chapter (isotactic PP from chiral
metallocenes), rather than being the
pillar of the whole book, is little more
than a well-written summary of a review
of the subject that is now almost 10 years
old, and leaves out the impressive development of new chiral metallocene structures and their stereoselective synthesis.
On the other hand, several chapters
delve into great details on aspects (often
the authors own work) that can be
regarded as curiosities rather than key
aspects of this catalysis. The reader who
is not a practitioner of this field might be
left with an unbalanced view, and with
the false perception that these catalysts
have remained confined to the academic
domain. The truth is quite the opposite.
There are also several inaccuracies (for
example, two adjacent chapters give
different mechanisms for polymerization of propene by the same catalyst,
Waymouths).
In summary, the most positive aspect
of the book is the breadth of coverage,
but it is not yet the definitive reference
work of this decade in the field of singlesite polymerization catalysis. If your
library has the 3rd edition of Comprehensive Organometallic Chemistry on its
shelves, then save your money, but if not,
then this book definitely has a place.
Luigi Resconi
Bioorganic and Medicinal
Chemistry of Fluorine
Edited by JeanPierre Bgu and
Danile BonnetDelpon. Wiley-VCH,
Weinheim 2008.
365 pp., hardcover
E 72,90.—ISBN
978-0-470-27830-7
Henri Moissan isolated elemental fluorine in 1886, a long-sought achievement,
for which he received the Nobel Prize in
Chemistry in 1906, shortly before his
death. This book by Jean-Pierre Bgu
and Danile Bonnet-Delpon, both at the
Centre National de la Recherche Scientifique (CNRS), who with their coworkers have developed the application
of fluorine compounds from organic
synthesis to medicinal chemistry,
appears shortly after the centenary of
Moissans death.
For many years, fluorine remained a
mere laboratory curiosity mainly of
interest to inorganic chemists, and organofluorine compounds were unknown.
In the late 1930s at Pennsylvania State
University, Joseph H Simons passed a
stream of fluorine over a carbon arc and
obtained a liquid fluorocarbon. During
World War II, under the code name of
“Joes stuff”, that compound found
application in the gaseous diffusion
process for isolating fissionable uranium-235 from naturally occurring uranium in the Manhattan Project that
developed the nuclear bomb. By the
mid-1950s the organic chemistry of fluorine was being developed, with the
preparation of more than 800 new
fluorocarbons.
Within two or three years, major
applications of organic fluorine compounds emerged, such as fluorine-containing general anesthetics. In 1954
Joseph Fried and E. F. Sabo provided
the first example of the tremendous
influence of a fluorine atom on the
biological properties of a molecule
when they introduced fluorine into corticosteroids. However, because research
has largely relied on naturally occurring
substances for inspiration, and organofluorine compounds are almost completely absent from natural products,
research on fluorine chemistry remained
more oriented towards the field of
materials than towards medicinal
chemistry. Furthermore, the only
known natural organofluorine compound, fluoroacetic acid, was highly
toxic.
Therefore, the organic chemistry
and bioorganic chemistry of fluorinated
compounds is a relatively new field that
really emerged only in the 1970s. Since
the 1990s, the growth of this field
accelerated in both research efforts
and importance.
As the organic chemistry of fluorinated compounds originally involved
2008 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
8155
Books
aromatic and heterocyclic substances,
fluorinated aromatic moieties predominated in pharmaceuticals and crop-science products. However, recent significant methodological improvements in
fluorination and trifluoromethylation
techniques, and the development of
new reagents and building blocks, have
resulted in an exceptional number of
fluorinated drugs and agrochemicals of
increasing variety and structural complexity. The percentage of fluorinated
pharmaceuticals increased from only
2 % in 1970 to 8 % in 1980, 13 % in
1990, and 18 % in 2000, with 6 drugs
among the leading 12.
Bioorganic and Medicinal Chemistry
of Fluorine was originally written in
French and published as Chimie Bioorganique et Mdicinale du Fluor (EDP
Sciences/CNRS Editions, Paris, 2005).
Actually, the English version is more of
a second edition, because the references
have been updated from 2004 to early
2007 for some chapters, some paragraphs have been completely modified
for clarity, and some new sections have
been added. Although its French origin
is betrayed in a few places by terms such
as “mineral” for inorganic and “fluorhydric acid” for hydrofluoric acid, the
meaning is always clear.
This book, which is the first comprehensive reference source devoted to the
influence of fluorine on the structural
and biological properties of molecules,
8156
www.angewandte.org
employs numerous examples of both
established and innovative fluorinated
drugs to provide an extensive overview
of the role of fluorine in pharmaceutical
research and development. Although a
considerable amount of data has been
collected during the last half-century,
many questions still remain about the
effects caused by the presence of fluorine atoms in biologically active molecules. In fact, the increasingly frequent
appearance of fluorine in new drugs has
usually resulted from structure–activity
studies rather than from rational predictions. Consequently, the authors try
to rationalize and understand the role of
fluorine in bioactivity.
The book is divided into two parts.
The first part (Chapters 1–3) deals with
general aspects of the specific properties
and preparations of fluorinated compounds, while the second part (Chapters
4–8) deals with the different classes of
these compounds and their biological
properties.
Chapter 1, “General Remarks on
Structural, Physical, and Chemical
Properties of Fluorinated Compounds”,
describes the principal effects that result
from introducing fluorine atoms into a
molecule. Chapter 2, “Overview on the
Preparation of Fluorinated Compounds”, focuses on the specific methods for preparing these compounds.
Chapter 3, “Effects of Fluorine Substitution on Biological Properties”, exam-
2008 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
ines the potential role of fluorine atoms
in the biological activity of molecules.
Chapter 4, “Fluorinated Analogues
of Natural Products”, Chapter 5, “Fluorinated Derivatives of a-Amino Acids
and Proteins”, and Chapter 6, “Saccharidic Fluorinated Derivatives”, deal with
these classes of compounds. Chapter 7,
“Inhibition of Enzymes by Fluorinated
Compounds”, discusses cases in which
fluorine atoms play a decisive role in the
inhibition effect and are important in
the discovery of drugs. Chapter 8, “Fluorinated Drugs”, deals with primary
drugs that are already on the market or
are in development. It includes a 5-page
appendix of International Nonproprietary Names and trademark names of
drugs, classified according to uses. An
index consisting of 13 two-column pages
facilitates location of material.
I am pleased to recommend Bioorganic and Medicinal Chemistry of Fluorine as an invaluable reference source
and stimulus to further research, for
pharmaceutical and medicinal chemists,
organic chemists, and biochemists in
academia and industry, and for
advanced students and instructors in
these fields.
George B. Kauffman
California State University
Fresno, CA (USA)
DOI: 10.1002/anie.200885643
Angew. Chem. Int. Ed. 2008, 47, 8155 – 8156
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chemistry, delpon, medicina, bioorganic, pierre, danil, edited, fluorine, bgu, jean, bonnes
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