BOOKREVIEWS
September 1967
/ -
1
z
K NHCOCHZCl NHCOCH,CH,Cl NHCO( CH,),Cl
R1
R?
Alp,
oc
987
Calcd, %----
H
C
H H 290-291 39.87 4 . 1 1 12.70 H H 144-143 61.41 4.73 11.94 S Ha 114-11.5 62.74 5.2i 11.27 H CH S 280-282 59.87 4.11 12.70 H NHCOCH,Cl H CH s 11.Y4 134-13,j 61.41 4.73 H ?;HCOCH,CH,Cl H CH S 122-1 23 62.74 .3.27 11.27 H S NHCO(CH,)?Cl H CH 162-163 61.41 4 . 7 8 11.94 N SHCOCH,Cl H C H1” CH 145-146 62.74 .i.27 11.27 CH 9 SHCOCH,CHzCl H CH, 143-144 64.00 5.73 10.66 CH s S H C O (CH,)3C1 H CH3 139-140 4.73 11.94 S H Hd 61.41 CH SHCOCH,CH,Cl H Hd 113-118 62.74 .i.27 11.27 S CH S H C O (CH2)sCl 5 .7 j 10.66 64.00 H H 139-141 S CH S H C O ( CH,),C1 Gave 3-amiiioisoquirioliiie on reactioii with HS(CH,CH&H 1 2 . * Gave 3-methyl-5-aminoisoquinoline CHJOH),. Anal. Calcd: C1, 14.26. Found: C1, 14.20. d Gave 5-aminoquinoline on reaction with CH CH
?;
w-chloroacyl chlorides with the appropriate aminoheterocycle. It was hoped to convert thea- to alkylating agents similar to those prepared by Elderfield and LeYon3 from 8-aniinoquiiiolineh but in several preliminary experiments these amides were readily hydrolyzed in reactiotis with S,S-bis( (2-hydroxyethy1)aniine aiid the route was ahaiidoned.
Experimental Section‘ Preparation of Amides.-The appropriate amiiioquiiioline or aminoiroquinoliiie was treated with the appropriate w-chloroacyl (2) (a) Clarkson College of Technology. (b) University of Miami. (c) To whom inquiries should he addressed a t Clarkson College of Technology. (3) R. C. Elderfield and E. F. LeVon, J . O r g . Chem., 25, 1576 (1960).
-Found, H
7--
?i
c 60 61 62 60 61 62 60 62 63 61 b2 63
14 46 78 04 60 70 90 48 69 44 73 81
4.14 4.73 3.39 4.14 4.84
5.5.5 4.65 .i . 0.3 3.90 4.96 .3,20 5.60
yc---N
13.00 11.71 11,16 12.68 12.24 11.10 11.68 11. 02?
10.4.7 11.92 11.29 10.66
on reaction with HN(CH1HN(CH,CH,OH),.
chloride under t,he conditions of Elderfield and Levon,, the coiiditioiis of IliGaiigi,5 or more conveniently in CHZCI, or CHClr to give after neutralization the amides listed in Table I. p-N,N-Bis(2-chloroethyl)aminobenzoylDerivative of 5 Aminoquino1ine.--Use of p-[N,?;-bis(2-chloroethyl)amino]betizoyl chloride and 5-aminoquinoline in the above sequence gave a 53% yield of solid, mp 169-172°. This compound exhibited no antineoplastic activity against \Valker carcinosarroma 256 a t 25 mg/kg. -4nal. Calcd for C20HI,C1,S30: C, 61.86; H, 4.Y3; X, 10.82: C1, 18.26. Foinid: C, 61.82; H, 5.00: ?;, 10.82; C1, 15.21. (4) Analyses h y Y:iang AIicroanalytical Laboratory, Ann .Irhor, N i c l r . Neltinr points are taken in capillaries and are corrected. ( 5 ) F. E. DiGangi, J. A m . Pharm. Aasoe., 44, 136 (1953).
Book Reviews The Epidemiology of Tropical Diseases. By OSCARFELSENFELU.mittee that toys with plans for research o i i tropical maladies. I t can be read profitably by epidemiologists and by laymen. The Charles C Thomas, Publisher, Springfield, Ill. 1966. xiv infectious process, including routes and vectors of infections, 488 pp. 16.5 X 24 cm. %14.i5. start off the book and lead next to control measures by sanitation Only an insignificant number of American medicinal scientists arid immunization. T h e next, four major sections are devoted to and ph3-sicians are working in the field of tropical diseases, in detailed discussions of the epidemiology of bacterial, mycotic, spite of the fact that almost 500,000 Americans have been sent inparasitic, rickettsial, and viral disease> encountered iri hot, to jungles where they lie in foxholes, wade through vector-infested humid belts: some of these infections overlap with coiiditions streams, and eat food that would be condemned as unsanitary i i i prevalent iri S o r t h America a+ well. The final section of the their home land. The reason for this apparent lack of interest book deals with iioiicommuriicahle diseaseb of nut,ritioiial and is, quite simply, money. The U. S. Public Health Service must occupatiotial origin, maligriancies, dent a1 xiid rardiovascular dismarshal1 its funds wisely for the health of the nation, and in the orders, and addiction and mental diseases. Here again the tropics iiow increasingly rare intervals of “peace,” tropical diseases prehold no privileged position, and much of what the author has ohsent iio major health hazard to most Americans. Most of the served there m-ould apply to domestic conditions. pharmaceutical industry sees little fiiiaricial incentive in producThe book is clearly written, well printed, aiid thorough1)ing drugs that the impoverished uiiderdeveloped countrieb in readable. There is at1 adequate subject irides, a i i c l at the end of tropical regionb could ill afford. This is a deplorable state of each aectioti a liat of references to books, i,ecetit monograph>, affairs both from a human and scientific point of view. Disand reviews. regarding our inherent humanitarian impulses to help our fellow A L F R E D BURGER men to rid themselves of disease, we appear to be condemned by circumstances and by unwise policies to send wave after wave of our best young males to fight in tropical countries for many years t o come. This alone should call for a major public. aiid private effort to sponsor researrh in tropical diseases. Svieiil ifDevelopmental and Metabolic Control Mechanisms and Neoically, huge uiiesploi,ed areas lure the mediriiial mid metiicul plasia. A Collect io11 of Papem Presented a t the Yineteetilh iiivestigator t o apply t o them esperimeiits iii fuiidameiital sciAnnual Symposium 011 Fundamental Cancer Research, 1965, at ence and clinical art. The University of Texas 11.D. Anderson Hospital and Tumor The textbook hy Felserifeld makes a valuable rotitributiori t o Institute. The Williams and Wilkins Company, Baltimore, thih iicylwted field :tiid shoiiltl he t ~ e q u i r ~t~endiiig d f o a~n y comSId. 1965. s 514pp. 16 X 23.7 cam. $16.00.
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