Journal of Medicinal Chevzistry, 1370, Vol. 13, S o . 5 1018
Yo surDose
nq/animal (ip)
vivors treated group
0.1
0.3 0 , .i 0 . .i 0 , ,i I. 1 , .j 0 ..-I 0 , *-> 0 ..i 0 . .i 0.5
*-,
yo sur-
% I
vivors treated group
stirvibvrs control group
0.1 0 . :3 0 ..i 0 .3
20 50 90 100
20 20 20 20
0 .3 0 . .i 0 .3 0 . .i 0.3 0 .*j 0.5
60 23 :30 100 60 0 90
8 20 13 87 60 33 li
"0
survivors control group
30 0
7 7
io
i 7 20
60 . 0i 60 x0
10 60 40 10 90
7 47 1:i 87 60 33 17
Dose mx/animal (ip)
surDdse mg/animal (ip)
vivors
treated group
Yo survi\ orzl control group
1.0
70
8
1.0
30
20
1. 0 1.0 1.0 1.0 1.0
50 90 60 70
8i 60 :3 3
io
8
1:%
2-aminobenzothiazole i t would appear that the antiviral effect is not improved by increasing the dose level above 0.; mg per animal. Acknowledgment.-The author is indebted to S. Gejer, G. Fuchs, E. Holubars, and 31. Brundin for skillful technical a 4 s t a n c e and to G. Westin for preparation of some of the substances.
H /
Dipurtn~enlof Chenzisiry, Gnivusity of Georgia, Athens, Georgia 30601
Received January 27, 1970
The ki10n-ri3biological activity of D-cycloserine (la), a broad spectrum :mtibiotic, led use to examine derivatives of this compound for antimalarial activity.
ANHK RJ 1 R=R=H b. R =aralkyl; R' = H c. R = H; R = a r a l k y l d. R = R = a r a l k y l a,
We have previously4 reported the synthesis of several derivatives of cycloserine having general structures l b (R = 3-hvdrosy-3-chlorobenzyl) and l e (R' = Ph3C). The pathway by which this was done is shown in Scheme I. In this report, several new Schiff bases (2) are described which can be reduced with KaBH4 to ( 1 ) Suppoi l w l i i i pari 1j.v ( ' c ~ ~ i L r a ,I).i-49-1!43-A1 ~l L)-2993 from tlie U. S. . i r m y Medical Hesearch a n d L)aveloymeut Comlnand. (2) T o \vlioiu inquiries alioiild be addreiiued. ( 3 ) Francie C. Neuhaus, in "Antibiotics," Vol. I, D. Gottlieb a n d P. L . Siiaiv, Ed., Springer-Verlag, Heidelburg, 1967, Chapter 2. (4) (a) C. 11. Stammer a n d J. D. McKinney, J. Org. Chem., 30, 3436 (IVti:); ( b ) K . .I. Payne a n d C. H. Stammer, ibid., 33, 2421 (1968).
lb
