Chemical Education Today
Book & Media Reviews
edited by
Jeffrey Kovac University of Tennessee Knoxville, TN 37996-1600
Top Drugs: Top Synthetic Routes (Oxford Chemistry Primer No. 90) by John Saunders Oxford University Press: Oxford, UK, 2000. 90 pp, ISBN 0-19-850100-5 (paperback). $15.95 reviewed by R. Daniel Libby
Top Drugs: Top Synthetic Routes is #90 in the Oxford Chemistry Primer series. According to the editor, Stephen G. Davies, books in this series “…have been designed to provide concise introductions relevant to all students of chemistry and contain only the essential material that would normally be covered in an 8–10 lecture course.” As the title suggests this member of the series is designed to explore synthetic routes to a number of important drugs. All of the compounds considered are or have been drugs used to treat human diseases. Thirty-six different drugs are grouped into 10 chapters organized according to classes of human disease treated: cardiovascular, gastrointestinal, and central nervous system problems as well as inflammatory and infectious diseases. Drugs investigated include captopril (hypertension), losartan (hypertension), nifedipine (angina), cimetidine (ulcers), omeprazole (antacid), fluoxetine (depression), diazepam (muscle relaxant), terfenadine (seasonal allergic rhinitis), zidovudine (AZT HIV), and norfloxacin (antibacterial). In the introduction, the author states, “Individual chapters are focused on collections of drugs that operate via the same mechanism. After an introduction to the discovery and mechanism of action, each drug is discussed in terms of its first synthesis and then later routes which have points of interest to organic chemists.” The author’s description is accurate. Each chapter provides a short history of the medical target (e.g., depression) as well as the logic for the original choice of potential drugs in terms of their physiological mechanism of action. These historical discussions provide valuable insight into the metabolic processes involved in the
target disease. This material is likely to be beyond the experience of typical synthetic organic chemistry students. Following the chapter introduction, between two and five separate drugs are presented. For each drug, an early successful synthesis is briefly outlined with a scheme illustrating structures of each isolable intermediate and one or more literature references. The author then identifies subsequent modifications of the original synthesis, explaining the goal and logic of the modification. Although the author provides a step-by-step presentation of the original synthesis, he does not explain the logic that led to the particular synthetic route. Starting materials are presented as given with no indication of how they were chosen. Then reagents for each step are provided but no suggestion of why the particular reagents were chosen. Readers interested in the synthetic logic of the original syntheses will need to consult the references provided. Unfortunately, several of the references are to patents, which generally provide little in the way of the reasoning used in devising particular synthetic paths. The considerations of modifications of original procedures provide insight into the problems with original syntheses and approaches to improving them, particularly with respect to asymmetric synthetic approaches. However, the particular improvements are again presented in a matter-offact manner with minimal consideration of why the particular process was chosen. On the whole, Top Drugs: Top Synthetic Routes provides valuable insight into the metabolic bases for rational drug design and some ways that existing syntheses may be modified to improve specific characteristics of the product. However, it does not deal significantly with the logic of synthetic design. Thus, this book may be of use to synthetic organic chemists accomplished in devising synthetic paths to desired target molecules, yet in need of more insight into the rational choice of target molecules. It will not be of very much use to students hoping to gain insight into the logic of synthetic design. R. Daniel Libby is in the Chemistry Department, Moravian College, Bethlehem, PA 18018;
[email protected].
JChemEd.chem.wisc.edu • Vol. 80 No. 2 February 2003 • Journal of Chemical Education
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