Book Reviews
Journal of Medicinal Chemistry, 2005, Vol. 48, No. 13 4487
Book Reviews Name Reactions in Heterocyclic Chemistry. Edited by Jie-Jack Li. John Wiley & Sons, Hoboken, NJ. 2005. xix + 558 pp. 19 × 24 cm. ISBN 0-471-30215-5. $125.00. Over the years several excellent texts devoted to the chemistry of heterocyclic compounds have appeared including, but certainly not limited to, “An Introduction to the Chemistry of Heterocyclic Compounds” by R. M. Acheson in 1960, “Principles of Modern Heterocyclic Chemistry,” by L. B. Paquette in 1968, “Heterocyclic Chemistry” by J. A. Joule and G. F. Smith in 1972, “Contemporary Heterocyclic Chemistry” by G. R. Newkome and W. W. Paudler in 1982, and the latest edition of “Heterocyclic Chemistry” by T. L. Gilchrist in 1997. This latest addition to the area combines the best features of its predecessors while organizing the text in a welcomed fashion of named reactions within different of heterocyclic systems. The contributing authors represent a diverse group of academic and industrial chemists with a brief foreword by E. J. Corey. A useful listing of acronyms and abbreviations used throughout the text appears at the beginning. Like Gaul, the book is divided into three parts, “Three- and Four-Membered Heterocycles” (with one chapter devoted to epoxides and aziridines), “Five Membered Heterocycles” (with six chapters covering pyrroles and pyrrolidines, indoles, furans, thiophenes, oxazoles, isoxazoles, and other systems), and “Six Membered Heterocycles” (with three chapters covering pyridines, quinolines, isoquinolines, and other systems). Within each chapter, coverage is, as the title indicates, organized into reactions achieving such status as to be recognized as a “name reaction”. The editor indicates that each name reaction is summarized in seven sections including a description, historical perspective, mechanism, variations and improvements, synthetic utility, experimental information, and references. The references cited at the end of each chapter are quite up to date and include several 2003 literature citations. This book will appeal primarily to graduate students in chemistry and medicinal chemistry and to professional research chemists. The coverage of material is extensive, but it can be adapted to the teaching of graduate chemistry and medicinal chemistry courses. “Name Reactions in Heterocyclic Chemistry” represents a major contribution to the field and is highly recommended. The only drawback to this text is its cost. Ronald F. Borne Department of Medicinal Chemistry School of Pharmacy The University of Mississippi University, Mississippi 38677 JM058210F 10.1021/jm058210f
Predicting Chemical Toxicity and Fate. Edited by Mark T. D. Cronin and David J. Livingstone. CRC Press, Boca Raton, FL. 2004. xviii + 445 pp. 18 × 26 cm. ISBN 0-415-27180-0. $98.95.
This volume consists of 19 chapters, logically divided into four sections, plus a brief introduction by one of the editors. Most of the 29 contributors are European or Canadian, and this choice provides a refreshing outlook on certain topics. The extensive list of abbreviations is welcome, even though many of them will be familiar to most readers. In his introduction, the editor makes the excellent point that lists of structures for which effects need to be predicted historically always grow more quickly than available predictive capabilities. This gives the lie to the argument still too often heard that hardware has rendered efficient algorithms unnecessary. The four sections are Methodology (considerations applicable to all QSARs), Human Health Endpoints, Environmental Toxicology and Fate, and Applications, by which the editors mean applications of QSARs in regulatory contexts. My experience suggests that this division accurately reflects differences in the subject matter. The Methodology section includes chapters on sources of toxicology data, calculation of physicochemical properties (two chapters), topological descriptors, quantum chemical descriptors, and a practical guide to building QSAR models. Each chapter provides a timely overview of its subject, although the first physicochemical property chapter, written by the two editors, is little more than a description of the various commercial software packages now available. To be fair, I must admit some surprise at the extent to which physicochemical property prediction has become a commodity business everywhere. The use of QSARs and expert systems to predict human health endpoints has met with limited success, and it is to the credit of the various contributors to the human health section that they do not make unjustified claims for these methods. Rather, for each topic (mutagenicity and carcinogenicity, toxicity from expert systems, metabolism and biotransformation, pharmacokinetics parameters) we learn what research has been done, what needs most to be done, and why successes have been limited. This is exactly the sort of state-ofthe-art description an overview volume should provide. The use QSARs for predicting environmental toxicology and fate is a very different activity from predicting human health endpoints primarily because the relevant endpoints are better defined and because many more high-quality data sets are available. An exception might be bioconcentration, where questions about what constitutes a steady state between the water column and the organisms can confuse measurement of the endpoint. A curious chapter in this section deals with developing QSARs for biodegradation using catabolicbased biosensors. I was not aware of this work, and I was surprised to learn of its successes. The final section deals with existing and proposed regulatory uses of QSARs. Here especially, the preponderance of non-American contributors ensures that European and Canadian activities are well-represented. The only reservation I have is that I believe Cronin
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Book Reviews
overstates the capabilities of ECOSAR, a program with which I am intimately familiar. I can recommend this volume as an overview of the state of the art expressed in the title. By today’s standards, the price seems reasonable, considering the amount of information presented.
or be able to do upon understanding the concepts and practical applications presented in the chapter. At the end of each chapter there is a summary of key points and workable problems with answers. Answers are conveniently provided either immediately or at the back of the book. Further readings related to the topic area of each chapter are also provided at the end of each chapter. These directed readings are primarily targeted to texts that will provide a more thorough discussion or account of the topics, although a number of primary journal articles are cited. The content and subject indexes in this book are very concise, perhaps a bit too concise considering the inherent less-guided approach users of a tutorial may seek to identify subject or content. As a tutorial chemistry text, a diverse number of fundamental concepts and examples are presented in a very concise and direct manner. The broad coverage of topics in this tutorial does afford sections where advanced concepts may outpace the undergraduate audience if one attempts to use this tutorial as a primary text. However, the explanations and discussions of mechanistic aspects for organic reactions employ sample reactions that are consistent with transformations undergraduate organic students should be familiar with. Overall, this book is an excellent tutorial resource, if not supplementary text, for providing students the fundamental basis of electron pushing and elementary concepts in organic mechanisms through advanced topics relating to mechanisms of organic reactions.
Gordon G. Cash United States Environmental Protection Agency Ariel Rios Building 1200 Pennsylvania Avenue NW Washington, D.C. 20460 JM0582266 10.1021/jm0582266
Mechanisms in Organic Reactions. By Richard A. Jackson. The Royal Society of Chemistry, Cambridge, U.K. 2004. vi + 199 pp. 19 × 24.5 cm. ISBN 0-85404642-9. £14.95. This book is the 23rd in a series of short tutorial chemistry texts focused on fundamental concepts taught in undergraduate science courses. As the title implies, the topics covered in this tutorial text are focused on chemical mechanisms in organic reactions. The first chapter is an excellent introduction to the fundamentals of organic reaction mechanisms, discussing the basics for drawing, formulating, and understanding mechanisms. This chapter also includes a short but noteworthy commentary entitled “Why Study Mechanisms?” The remaining six chapters each quickly delve into understanding and applying more in depth concepts relating to kinetics, transition states, anions and nucleophilic reactions, cations and electrophiles, radicals, and the fundamental aspects of frontier orbitals as related to transition states and cyclization reactions. Each of the seven chapters is prefaced with a short list of aims, which essentially outline what a student should know
Robert J. Kerns Division of Medicinal and Natural Products Chemistry College of Pharmacy University of Iowa Iowa City, Iowa 52242 JM058229I 10.1021/jm058229i
