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Modern medicinal chemistry
44
Book Reviews Organic Chemistry b y M a r y e A n n e F o x a n d J a m e s K W h i t e s e l l . p p 870. J o n e s a n d B a r t l e t t , B o s t o n a n d L o n d o n . 1994. £21.95 ISBN 0-86720-207-6 This is a refreshing student text on organic chemistry which contains a considerable amount of biochemistry too, although it has one slightly fatal flaw from the biochemical point of view (see below). The organisation is non-traditional in the sense that the whole is divided by reaction type rather than by functional group. This means that the aromatics make their appearance much earlier than would otherwise be the case. The authors say that they have tried to write the chapters so that they "go somewhere" as in the unfolding plot of a novel, and to a large extent I think that they have succeeded. There is also a strong emphasis on three-dimensional structure (good for potential biochemistry students) and which naturally sets the scene for chapters on biomolecules and biophenomena later on. Furthermore, the wealth of real and everyday examples, almost from page 1, makes the text interesting to students. 'Chemistry', say the authors, 'is an enabling science . . . providing synthetic routes to new compounds needed to feed, clothe, house, defend, transport and provide health care for human beings'. They also say that they wanted to show what organic chemists actually do in a laboratory. I think they have succeeded less well in this aim. Although the reactions and reaction sequences are there (especially for the synthesis of 'relevant' compounds), there is little on apparatus and technique, and indeed the two most powerful techniques, chromatography and spectroscopy, are collected together in a separate chapter (chapter 4). Surprisingly little is said about HPLC. The chapters start out on structure and bonding, alkanes, alkenes, arenes and alkynes and functional groups containing heteroatoms. Chapter 4 is on chromatography and spectroscopy, and chapter 5 is on stereochemistry. Chapters 6 and 7 are on reaction mechanisms and chapters 8 to 24 are on reaction types. The subsequent chapters then deal with multistep syntheses, polymeric materials, naturally-occurring compounds, and on to non-covalent interactions and recognition, catalysed reactions, biological redox reactions, energy storage in organic molecules, and finally the molecular basis for drug action. Some of this is very well done although it often displays a chemist's view of things and especially of structures. Would students be confused by seeing glycolysis written like this, for example? And is it stereochemically sound? O
O
OH OH O"~'OH
H0 ~OH OH
OH
0 ~ O ~
Glucose-6-phosphate
OH O/I~'OH ~ HOH OH
Fructose-6-phosphate
Moreover, the 'logic' displayed is chemical logic rather than biological logic. Also, energy is dealt with in terms of 'exothermic' and 'endothermic', although the values are quoted as AG °" I thought the section on enzymes was quite good and gave an excellent overview of both catalysis and chiral recognition. The other parts on metabolism, unfortunately, deal with acids rather than ions (eg isocitric acid rather than isocitrate), whereas biochemists have been trying to wean students on to the idea that at cellular pH most of the 'acids" of metabolism will be ionised. There is also rather little on the determination of macromolecular structure, although this is perhaps understandable
BIOCHEMICAL
EDUCATION
23(1) 1995
given the less than 1000 pages remit the authors seem to have set themselves. For the biochemist the heinous crime is committed on pp 760761 where it is stated that the Krebs cycle was discovered by Edwin Krebs and his collaborator Edmund Fischer, both of Washington University at St Louis, and who were awarded a Nobel Prize in 1992. It wasn't, but they were. At a time when undergraduate students are walking away from, or avoiding, chemistry courses because they think they are either hard (ie intellectually demanding?) or irrelevant, or both, this sort of book may help them to make the link between organic chemistry and biological chemistry. It is an important link because whatever the students think, living things work by chemistry and a knowledge of chemistry is still important for understanding how they work. In the UK it would probably only appeal to the brighter more committed students. Furthermore, there is strong evidence of the 'different language' used by chemists compared with biochemists, some examples of which have been mentioned above, which may hinder students' acceptance. Nevertheless, if students could be persuaded to get to grips with this book and one of the modern biochemistry texts they would be doing themselves very well. [In addition to the text there are available a Solutions Manual and Study Guide, a set of 50 colour transparencies, an Instructor's Test Bank, a Computerised Test Bank, and a plastic model making kit.] E J Wood
M o d e r n Medicinal Chemistry by J o h n B T a y l o r a n d P e t e r D K e n n e w e l l . p p 286. Ellis H o r w o o d , C h i c h e s t e r . 1993 ISBN 0-13-590399-8 This is an attractive volume, part of the Ellis Horwood series in pharmaceutical technology, and described by the authors as an update of an earlier text they produced in 1981. It is designed for use at the first and second year undergraduate level. Medicinal chemistry is defined as the study of those chemicals which have potential beneficial effects on disordered living systems. The authors then go on to describe its relation to other fields of endeavour, such as pharmacology and medicine. This perspective will be very instructive to students. Another notable feature of the book, which adds much to its interest, is the sociohistorical approach adopted in the first forty pages or so. Thus there is a table of important developments in medicinal chemistry, ending up in 1988 with the first biochemically engineered protein pharmaceuticals. I enjoyed reading about the evolution of the pharmaceutical industry, originating in the apothecary's shop. The authors explain, for example, why the Swiss became players in the premier league of the industry. There is a valuable section on the international characteristics of patients and a discussion of the value of good timing in the face of a development period of eight years (for most drugs) cutting into a patent lifetime of twenty years. From the strictly biochemical point of view the most crucial part of the book is that section entitled The pharmacodynamic phase, for this deals with membranes, receptors, primary and secondary messengers, enzymes, RNA as an enzyme, and catalytic antibodies. Another interesting section is on Drug discovery processes, in which, inter alia, the authors discuss specific cases of the successful design of ligands by the use of models and computer graphics. The formulae are very well set out and the language is lucid. This will be a valuable book for the proposed readership. John Candlish
Book Reviews Organic Chemistry b y M a r y e A n n e F o x a n d J a m e s K W h i t e s e l l . p p 870. J o n e s a n d B a r t l e t t , B o s t o n a n d L o n d o n . 1994. £21.95 ISBN 0-86720-207-6 This is a refreshing student text on organic chemistry which contains a considerable amount of biochemistry too, although it has one slightly fatal flaw from the biochemical point of view (see below). The organisation is non-traditional in the sense that the whole is divided by reaction type rather than by functional group. This means that the aromatics make their appearance much earlier than would otherwise be the case. The authors say that they have tried to write the chapters so that they "go somewhere" as in the unfolding plot of a novel, and to a large extent I think that they have succeeded. There is also a strong emphasis on three-dimensional structure (good for potential biochemistry students) and which naturally sets the scene for chapters on biomolecules and biophenomena later on. Furthermore, the wealth of real and everyday examples, almost from page 1, makes the text interesting to students. 'Chemistry', say the authors, 'is an enabling science . . . providing synthetic routes to new compounds needed to feed, clothe, house, defend, transport and provide health care for human beings'. They also say that they wanted to show what organic chemists actually do in a laboratory. I think they have succeeded less well in this aim. Although the reactions and reaction sequences are there (especially for the synthesis of 'relevant' compounds), there is little on apparatus and technique, and indeed the two most powerful techniques, chromatography and spectroscopy, are collected together in a separate chapter (chapter 4). Surprisingly little is said about HPLC. The chapters start out on structure and bonding, alkanes, alkenes, arenes and alkynes and functional groups containing heteroatoms. Chapter 4 is on chromatography and spectroscopy, and chapter 5 is on stereochemistry. Chapters 6 and 7 are on reaction mechanisms and chapters 8 to 24 are on reaction types. The subsequent chapters then deal with multistep syntheses, polymeric materials, naturally-occurring compounds, and on to non-covalent interactions and recognition, catalysed reactions, biological redox reactions, energy storage in organic molecules, and finally the molecular basis for drug action. Some of this is very well done although it often displays a chemist's view of things and especially of structures. Would students be confused by seeing glycolysis written like this, for example? And is it stereochemically sound? O
O
OH OH O"~'OH
H0 ~OH OH
OH
0 ~ O ~
Glucose-6-phosphate
OH O/I~'OH ~ HOH OH
Fructose-6-phosphate
Moreover, the 'logic' displayed is chemical logic rather than biological logic. Also, energy is dealt with in terms of 'exothermic' and 'endothermic', although the values are quoted as AG °" I thought the section on enzymes was quite good and gave an excellent overview of both catalysis and chiral recognition. The other parts on metabolism, unfortunately, deal with acids rather than ions (eg isocitric acid rather than isocitrate), whereas biochemists have been trying to wean students on to the idea that at cellular pH most of the 'acids" of metabolism will be ionised. There is also rather little on the determination of macromolecular structure, although this is perhaps understandable
BIOCHEMICAL
EDUCATION
23(1) 1995
given the less than 1000 pages remit the authors seem to have set themselves. For the biochemist the heinous crime is committed on pp 760761 where it is stated that the Krebs cycle was discovered by Edwin Krebs and his collaborator Edmund Fischer, both of Washington University at St Louis, and who were awarded a Nobel Prize in 1992. It wasn't, but they were. At a time when undergraduate students are walking away from, or avoiding, chemistry courses because they think they are either hard (ie intellectually demanding?) or irrelevant, or both, this sort of book may help them to make the link between organic chemistry and biological chemistry. It is an important link because whatever the students think, living things work by chemistry and a knowledge of chemistry is still important for understanding how they work. In the UK it would probably only appeal to the brighter more committed students. Furthermore, there is strong evidence of the 'different language' used by chemists compared with biochemists, some examples of which have been mentioned above, which may hinder students' acceptance. Nevertheless, if students could be persuaded to get to grips with this book and one of the modern biochemistry texts they would be doing themselves very well. [In addition to the text there are available a Solutions Manual and Study Guide, a set of 50 colour transparencies, an Instructor's Test Bank, a Computerised Test Bank, and a plastic model making kit.] E J Wood
M o d e r n Medicinal Chemistry by J o h n B T a y l o r a n d P e t e r D K e n n e w e l l . p p 286. Ellis H o r w o o d , C h i c h e s t e r . 1993 ISBN 0-13-590399-8 This is an attractive volume, part of the Ellis Horwood series in pharmaceutical technology, and described by the authors as an update of an earlier text they produced in 1981. It is designed for use at the first and second year undergraduate level. Medicinal chemistry is defined as the study of those chemicals which have potential beneficial effects on disordered living systems. The authors then go on to describe its relation to other fields of endeavour, such as pharmacology and medicine. This perspective will be very instructive to students. Another notable feature of the book, which adds much to its interest, is the sociohistorical approach adopted in the first forty pages or so. Thus there is a table of important developments in medicinal chemistry, ending up in 1988 with the first biochemically engineered protein pharmaceuticals. I enjoyed reading about the evolution of the pharmaceutical industry, originating in the apothecary's shop. The authors explain, for example, why the Swiss became players in the premier league of the industry. There is a valuable section on the international characteristics of patients and a discussion of the value of good timing in the face of a development period of eight years (for most drugs) cutting into a patent lifetime of twenty years. From the strictly biochemical point of view the most crucial part of the book is that section entitled The pharmacodynamic phase, for this deals with membranes, receptors, primary and secondary messengers, enzymes, RNA as an enzyme, and catalytic antibodies. Another interesting section is on Drug discovery processes, in which, inter alia, the authors discuss specific cases of the successful design of ligands by the use of models and computer graphics. The formulae are very well set out and the language is lucid. This will be a valuable book for the proposed readership. John Candlish