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Book Review Nucleotide Analogues as Antiviral Agents. (ACS Symposium Series Vol. 401). Edited by J. C

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plexes with C , symmetry, offers an interesting detailed insight into the development work needed to achieve spectacular successes of this kind.
The last contribution in the book describes the structures
of zeolites and ways of modifying them for specific purposes,
then indicates how they can be used for organic syntheses; up
to now these have been used mainly on an industrial scale for
producing basic chemicals.
Altogether the book is a very useful guide to the subject of
catalysts in organic synthesis, which has a promising future;
in particular it offers beginners a straightforward introduction to this field. All the articles are competently written and
thorough, and are therefore likely to be frequently cited. It
would be difficult at present to find other reviews presenting
the current state of knowledge in such a concentrated form.
One can only hope that the price, which has increased further
to DM 78.00-too much for a paperback in my view-will
not prevent this interesting book from reaching a wide readership that will include students.
Hans4 Altenbach [NB 1051 IE]
Institut fur Organische Chemie
der Universitat-Gesamthochschule Paderborn (FRG)
Nucleotide Analogues as Antiviral Agents. (ACS Symposium
Series, Vol. 401). Edited by J. C. Martin. American Chemical Society, Washington, DC (USA) 1989. viii, 190 pp.,
hard cover, $53.95.--ISBN 0-8412-1659-2
This book is a collection of papers presented at a symposium held on the occasion of the 196th meeting of the American Chemical Society in September 1988. As the editor notes
in his introduction, efforts to develop antiviral nucleoside
and nucleotide analogues as an answer to the AIDS epidemic
have been greatly increased in the last few years. The majority of the nucleoside analogues used up to now, of which
3‘-azidothymidine and 9-(hydroxyethoxymethy1)guanine
(Acyclovir) are the two most important, are effective in the
form of 5’-triphosphates. The phosphorylation proceeds via
three steps, one of which is often a bottleneck-for example,
in the case of azidothymidine this is the phosphorylation of
the 5‘-monophosphate to the diphosphate. Thus it already
became apparent some time ago that, instead of nucleoside
analogues, one might try to introduce nucleotide analogues
with potential antiviral activity into the cells. Since one of the
obstacles to the uptake of nucleotides is that they can be
broken down by enzymes in the plasma membrane, phosphate analogues that cannot be broken down in this way
seem to offer especially good chances for successful uptake.
Consequently several chapters of the book are mainly concerned with results obtained using the stable phosphonate
derivatives. In addition, however, there are separate chapters dealing with other derivatives, e.g. with nucleoside-5’amines and -acetamides (Chapter 7), nucleoside-5’-sulfamates (Chapter 9), nucleotide dimers (Chapter 11) and
oligonucleotides (Chapter 12).
As the book is a collection of articles by different authors,
the quality of the contributions varies. For example, some
contain unnecessarily extensive tables (pp. 10, 57,60,61 and
67) which make it difficult for the reader to distinguish essentials from non-essentials. Also very often the absence of compound names under their structural formulas-where these
are given-is confusing, as it makes it difficult to quickly
relate them to the text. The book is evidently intended for
experts, for whom the meanings of the many abbreviations
are obvious, and who will know, for example, that DHPG,
820
0 VCH Verlagsgesellschaft
mbH. 0-6940 Weinheim, 1990
which incidentally does not appear in the index, is identical
to Ganciclovir. As is often the case in symposium proceedings, every article stands alone and no account is taken of
other articles with which there is an overlap of subject matter
or an amplification of a topic, as, for example, in contributions 4 and 5 which deal with the compounds 9-(2-phosphony1methoxy)ethyladenine (PMEA) and 9-(2-phosphony1methoxy)ethylguanine (PMEG). No doubt in order to
produce this symposium volume as cheaply as possible, the
text is very closely printed throughout, and this has not exactly made the book user-friendly. Also it seems a little
strange that in the index entries referring to azidothymidine
are found not only under this abbreviated name but also
under “3‘-azido-2’,3’-dideoxythymidine”.
In addition to the more general discussions the book contains a few items of information which I found especially
interesting, not least because they could provide a stimulus
for future experiments. For example, it is remarked on pages
80 and 85 that phosphonate derivatives often show higher in
vivo than in vitro activity. Unfortunately no further commentary on this is given. Another interesting result reported but
not explained further is that some phosphonate alkyl esters
also show antiviral activity (p. 32).
This book is the first of its kind on antiviral nucleotide
analogues. Although none of the compounds discussed here
has yet been cleared for clinical use, it becomes evident from
reading the book that this is a class of compounds with great
potential, and that further systematic research on these is
justified. Despite the shortcomings mentioned, the book provides a good basis of material for the specialist.
Fritz Eckstein [NB 1053 IE]
Max-Planck-Institut fur Experimentelle Medizin,
Gottingen (FRG)
Nitration. Methods and Mechanisms (Organic Nitro Chemistry Series). By G. A. Olah, R. Malhotra, and S. C. Narang.
VCH Verlagsgesellschaft, Weinheim, VCH Publishers,
New York 1989. xii, 330 pp., hard cover, DM 145.00.ISBN 3-527-26698-410439573-144-4
The third volume to appear in the Organic Nitro Chemistry Series, this book deals exclusively with aspects of nitration in organic chemistry. In keeping with the preceding two
volumes (Nitrazoles and Nitrile Oxides, Nitrones and Nitronates in Organic Synthesis), it provides a broad survey of
the subject, encompassing in four chapters many of the
methods and mechanisms for the nitration of aromatic and
aliphatic compounds.
After a brief introduction in Chapter 1 (8 pages, 21 literature citations), the authors go on in Chapter 2 (108 pages,
264 literature citations) to describe preparative methods for
aromatic nitration. Numerous examples of the great many
reagents used for nitrating arenes appear mainly in tabular
form, accompanied in the text by the corresponding methods.
The authors have devoted a great deal of space in one
section of Chapter 2 to nitration with nitronium ions; unfortunately, the examples in this section are not as complete as
those from the section on nitration with nitric-sulfuric acid
(isomer-distribution data). Although this format does not
allow for comparison of aromatic nitration methods by way
of example, it gives the reader a good, comprehensive
overview. Some neglect is also apparent in the cursory treatment of homolytic (i.e., free-radical) and, more importantly,
nucleophilic nitration, considering the significance of these
0570-083319OjO707-08208 03.50+ .2510
Angew. Chem. Int. Ed. Engl. 29 (1990) No. 7
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