BOOKREVIEWS
Xovember, 1964 9-( 3-ThienyI)anthracene.-This compound was obtained essentially as was the L2-isomer’ above in 80% yield from the corresponding ketone using hydrobromic acid as the catalyst. Recrystallization from absolute ethanol gave an analytical sample as yellow needles, m.p. 122.0-122.5”, which fluoresced green under ultraviolet light.
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Anal. Calcd. for CtsHl&3: C, 83.03; H, 4.65; S, 12.32. Found: C, 83.10; H, 4.76; S, 12.06. The black 1 :2 adduct with 2,4,7-trinitrofluorenone melted a t 167-168”. Anal. Calcd. for C 4 4 H d 6 0 ~ S : C, 59.33; H, 2.49; N, 9.43; S,3.60. Found*: C, 59.44; H,2.53; N,9.38; S,3.37.
Book Reviews The Neomycins and Related Antibiotics. By KENNETHL. RINEHART, JR. John Wiley and Sons, Inc., Kew York, N. Y. 1964. 136 pp. 12 X 18 cm.
H. J. Rogers considere tha structure and functions of bacteria us. mammalian cells, and derives from these facts theories of
action of the sulfonamides and antibiotics which affect the synthesis of the bacterial cell wall. I n a well-written chapter, R. The antibiotic neomycin was discovered in 1949 and the fact Knox discusses theoretical aspects of the strategy and tactics of that its gross architecture and stereochemistry were not comantibacterial chemotherapy, from serendipity through in vitro to pleted until 1962 attests to the degree of difficulty this type in vivo requirements. D. J. Kushner writes about the resistance of problem presents. The chemical and medical literature has of bacteria to harsh and destructive environmental conditions desperately needed clarification in the neomycin field due to the such as heat, chemical concentrations, radiation, pH, heavy large number of similar and identical antibiotics which have been metals, enzyme inhibitors, surfactants, and disinfectants reported throughout the world. To this end Professor Rinehart Special topics include the chemotherapy with sulfonamides has done an excellent job and yeoman service in identifying and (L. Neipp) and the pharmacology of these drugs ( R . E. Bagdon ) correlating these substances. It was fortunate perhaps that two the nitrofurans ( H . E. and XI. F. Paul), topical antibacterial, closely related antibiotics, kanamycin and paromomycin, appeared ( R . J. Schnitzer), and therapeutic agents for tuberculosis (G. Ps on the clinical horizon in the late fifties since techniques used in and A. S.Youmans) and leprosy (P. C. Ekman). These special. the degradative procedures of one aided progress in the others. chapters are searching and critical evaluations of available. The book offers many interesting examples in the application methodology and the meaning of the procedures, and should of periodate oxidation, Hudson’s rotational rules, and nuclear , satisfy the demanding reader as well as those who look for overmagnetic resonance to the elucidation of oligosaccharide strucall information on one of these subject,s. tures. In some instances, however, structures have been postuUXIVERSITY OF VIRGIKIA ALFREDBURGER lated by presumptive rather than conclusive evidence but are CHARLOTTESVILLE, VIRGINIA interesting nonetheless in that they offer the reader a mental exercise in sugar conformational analysis. Of particular interest is the novel use of cuprammonium rotation data to the determination of absolute configuration of monosubstituted deMetabolic Inhibitors-A Comprehenisive Treatise. Volume 11. oxystreptamines. A welcome addition to the chemical studies is Edited by R. X. HOCHSTER and J. H. QUASTEL. Academic a chapter on biosynthetic considerations. Although incomplete, Press Inc., New York, N. Y. 1964. xvii 753 pp. 15 X it should offer the microbiologist valuable information relative to 21.5 cm. $29.00. antibiotic precursor studies. We know that the multitude of natural metabolites in a given THEODORE H. HASKELL PARKE, DAVISAND COMPANY “living” system balance each other to produce the “normal” ANNARBOR,MICHIGAN condition of the system. A deletion of one or several metabolites upsets this balance. This situation may remedy itself by the establishment of a new balance in which an induced overproduction of a previously less active metabolite makes up for the Experimental Chemotherapy. Volume 11. Chemotherapy of deletion of the lost vital factors. Or else, an extraneous chemical, and Bacterial Infections. Part I. Edited by R. J. SCHNITZER a drug, or an internal chemical arising through an induced physiF. HAWKISG. Academic Press Inc., New York, N. Y. 1964. cal change of the biochemical environment may restore the upset xvii 614 pp. 16 X 23 em. $23.00. [For a review of Vol. balance, occasionally upsetting another facet in an undesired I, see J . X e d . Chem., 6,825 (196311. side effect. Whatever we insert into a biological system, be it a In almost all fields of chemotherapy the triumphs of the late nutrient or a corrective medicinal agent, will preoccupy enzymes, 1940’sand the early 1950’shave been dampened by the emergence tie up other natural chemicals, or cause them to react chemically, of drug-resistant organisms, and the flare-up of nearly forgotten and thereby temporarily or permanently remove them from the infections in less treatable, or even untreatable, forms. Moreintegrated biochemical scene. All these substances are metabolic over, systemic antibacterial therapy is mostly bacteriostatic antagonists. They range from the irreversible inhibitors to the rather than bactericidal, and as G. P. and A. S. Youmans put it kinetically most unstable antimetabolite systems; they interfere in the present volume (p. 394), “there is, therefore, a real need for with the biosynthesis of needed metabolites, or compete with the new and more eradicative drugs.” This should not detract from finished product for a reactive site of a macromolecular biothe magnificent achievements of the antibiotics and the synthetic catalyst. antibacterial agents which have contributed so much to increased The present volume, the second and the last one in this series, longevity and healthier living. Nevertheless, the appearance of a attempts t o cover the kaleidoscopic variety of all grades of antinew treatise on all aspects of bacterial chemotherapy is a timely metabolites which have not been discussed in Volume I [see event and should guide the investigator to future needs of reJ . Med. Chem., 6,828 (1963)]. Expert authors have been chosen searches in this field. for each chapter, and each appears to have done his level best t o The antibacterial dyestuffs, with emphasis on acridine derivasurvey critically, broadly, and with restraint his assigned field tives, are reviewed by C. H. Browning. This section is the only about which he knows so much. The editors must have had a connection to the early history of antibacterial agents in this hard task coordinating these interwoven and overlapping chapbook. It is to be regretted that space did not permit the inters. Just as even an experienced biochemist will be troubled clusion of many other older antibacterial agents which were tried by the relative lack of specificity of the vast majority of antiand discarded before the advent of decisively active drugs for a metabolites, thus the editors must have suffered from the overgiven infection. Many valuable “leads” are stacked away among lapping of chapters. However, this could have been corrected those forgotten compounds. In a time when radical departures had the editorial work been done more carefully. T o take a from useful drugs are being sought to overcome problems of specific point, the well-presented chapter on mono- and polyamine bacterial resistance and persistence, some of those old studies may analogs by E. A. Zeller is followed by a survey of inhibitors of well have been unearthed again. catecholamine metabolism (T. L. Sourkes and A. D’Iorio) which
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ROOKREVIEWH
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repeats (pp. 89-90) some of the facts discussed by Zeller, but i n a n incomplete and out-of-date way. Obviously, this reviewer is not expert in the 22 different topics which make up this volume, but was left uneasy by this and similar examples of lack of unity and uniformity. The reader who expects to learn all about the antimetabolites surveyed in each chapter should realize that a tq-o-volume treat,ise cannot cover a subject which would require BY monographs for comprehensive coverage. The metabolic inhibitory aspect of each compound has been stressed, justifiedly, a t t h e expense of a general survey. As long as this is kept in rriind, the suggest,ive of hiindretls reader will find :I wealth of iiifiirii~:~tiiin of new ideas in a11 fields from Iii~ic~hemistry i o sl)ec,i:il :irc:ip of hicilogy :tiid medicine.
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able i n the present book. It represents the first, one in the series t o he followed by “Structure Determin:rtion of National Products Iiy AIass Spectr(imetry,” Vol. I, .4lk:iloids: a n d Vol. IT, Pteroitls, Sesquiterpenes, et,(,., the areas i n whirti thc H!:tiiford gr(iu1) h : i ~ ni:tcte niassive iv )nt,ributi ons, The detailed consideration of fragineritatiori patterns :is i i i fiuen(w1 h y the presence of various functional groups is prcijrctril very clearly :tiid presented with great c.onfiderice. X i i r w c i ~ i i r r in the field, however, should not overlook the fact that son it^ spectra Lire full of pitfalls. The authors witrn aiid (*:tiition:Lg:iiiist lack of ~1iscriiiiiii:~ti~iii. They also poirit oiit sevei,:il p1:~iisiMrI ) i i t :is yet unproved ~nerhnriismsahirli c.~itiltltic understoncl bettcar liy proper hiheling nf c~nnipo~i~itls with iscitoliw a i i d r ~ ~ - e ~ : i ~ i i i r ~I/.~ i t i i i ~ i t
I tic l i o i i l i is l i i i * i t l l > ~tvritten : i n t i its fiirni;it is :iiir:iidvifi. i~)upledivith a lniv price Itinke tlic IJ(IIII< :L Tht?se c~cin~idci~:ition~ w r y iirip(irt:~nt:idtliticiri t o the li\)rary i i f :in orgnnic c~hoiriisti.y hIi(ir:it(iry. - 3
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~ t i , : s E i R c , [ i~,.\rroIt.\ToItiics
NORRI:IIT
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Absorption and Distribution of Drugs. Edited by T. B. 131s~~. ISM T,II.I.Y .ANI> COMP.~SV lsI~I.tx.\PoIJs6, Ixn1.4s 4 Foreword by SIRC H ~ R L E~ S ~ D L I F IThe . FVilliams and Wilkins 270 pp. 14.5 x 22 cni. Co., Baltimore, 3rd. 1964. xi $7.50.
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In 1963, the British Association of AIedical Advisors in the Pharmaceutical Industry held a syrnposiurn on fact.ors affecting the absorption and distribution of drugs. The papers presented ( i n t,hat occasion are collected i n this little voluiiie. They range from two superb surveys of H. H. Hrcidie (physico-cheniicd factors in drug absorption, and distribution and fate o f drugs: tjherapeutic implications) to sucali prac.tira1 matters as rhernic~:il (N. J. Harper) and pharmaceutical ( K . E;. Lees) manipulatioii nnd therapeutic efficacy. There are good discussions 011 physiological barriers, the blood-brain barrier (11.IV. 13radbury), and the placental barrier (J. Ginshurg). Several chapters deal with alirnent,ary absorption (I>. H. Siiiyth: ,J. 4. 1,. Gorringe ant1 E. AI. Sproston; J. 11.Payne), and others with the absorption c i f specific drugs like steroids, spironolactone, hypot,ensive agents, salirylates, hematinics, and ohemotherapeiiti(, (espec:i:illy spirar n y i n and isomet:trriidiiin~) and arnehicidal agents. Thus, the reader will find chapters on fundanient:il queutioris of passage. through diverse membranes, specaific. answers t i i suc*hproblenis :is t’heabsorption of quaternary s:ilt,s, arid new ideas aiiout forrnulation procedures which might retard n r fac,ilitiite ahsorption :is thr need arises. Symposia reflect, n:tturallp enougfi, tiit. opiriions of those experts whom the arrangers have I)een : h l r t o persuade t o ptrticipate. In the present case, both the program ilkiairnim and thv editor of the volume have done an unusually giiod jnh, as :I result o f which the whole pic>tureof drug absorpticiii h:ts been presented with clarity and detachnieiit. Any ph:trniacdiigist, ph>-sici:m, or chemist vonrerned with protileins i i f :i,l)sijrptic~riwill profit, friirii this c.onip:tc-t book.
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Interpretlition of Mass Spectra of Organic Compounds. BY H. BUDZIEIEWICZ, C. DJERASS~, and D. H. WILLIAW. Holden271 pp. 26 X Day, Inc., SPn Francisco, Calif. 1964. xiii 19 cm. $8.75.
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I n addition to its established use in the determination of stable isotopes, mass spectrometry remained for years an analytical tool of the petroleum chemist until Stenhagen, Ryhage, Beynon, lIcLafferty, and others realized its potentialities in structure elucidation of organic compounds. More recently, Biemann applied mass spectrometry t o the structure determination of complex indole and related alkaloids, demonstrating the fact t h a t physical methods can become extremely useful tools in the prartire of organic chemistry when an organic chemist himself beromes acquainted with physical methods and learns t o interpret physical data available t o him through the use of sophisticated electronic instruments. This statement particularly applies to Djerassi and his volleagues who have been ronducting extensive work in mass spectrometry of various (*lassesof organic compounds and are making their own results as well as those of other workers avail-
The Chemistry and Therapy of Disorders of Voluntary Muscles. J3y E. G. MURPHY, University of Toronto, with an introduction by G. R. WILLI.\>is. Charles C Thomas, Publisher, 123 pp. 16 X 23.5 mi. $6.50. Springfield, Ill. 1964. siv
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The sheer fact that :t clinician, introdured by a hiorhenlist,, will write a hook on the cahemist,ry as well as the therapp of musrular diseases shows the inipact, of modern niedirinal and biochemiral thought on coniplicatetl medical problems. After decades of fruit,less trials and errors, using every type of drug, vitamin, hommone, amino acid, sugar, and what-have-you, and every niechanical arid elect r i d t,re:itment,,a rational scientific approach holds the best prnniise of success in devising therapies for these crippling and killing disorders. The introductory chapter sets forth in simple language the knoxvn facts ahout t,he hiiichemistry of muscle fibers, contraction, :tnd relaxation. The remaining chapters are devoted i , o muscle diseases: musriilar tlyst rophy, the rnyotonias, periodic paralysis, \lrArdle’s syndrnme. :iriite niyoglobinuria, polyniyosit,is, myhenia gr:Lvis, :inti :issorted iii>~~pathies. I n earh of 1,hese rlrnpters the pathology and any Iino\vn c*heniical abnormalities of the discirder :tre tlisciissetl, f ( i l l i r w d Iiy the :tlmost pit,ifiil met,hods r i f treatmerit av:til:tl>lt>. The sni:ill h < i ( i l
