Uiazo, Bronio, and Jlesyloxy Ketones
ab
Biological _~lkylatiiig iigentsiCL
657
BIOLOGICAL ALKYLATIXG AGENTS
September 1965
T.4BLE
1
INDOLE DERIVATIVES
I
H hI.p., "e.
x
H.
Nu.
yo calcd.
Formula,
54 found
-----
Infrared, f i - - - SEN C=O ROS02CH3
NH
I I1
H H
5-COCOCHNZ 3-COCOCH2Br
148-150 dec. CllH;N302 N : 19.71 148-149 Cl1HsBr?jO2 Br : 30.04
19.52 3 . 0 8 s 30.29 3 . 0 7 5
4.70s
I11
H
3-COCOCHzOSO&Ha
197-198
Ci2HllN068
11 40
11.163.06s
...
11T
CHaO 3-COCOCHKS CHaO 3-COCOCH2Br
150 dec. 177-178
C12HgN303 E: 17.3.5 C12H10BrN03Br: 26.99
17.54 3 . 1 0 s 27.20 3 . 0 5 s
4.72s
TI
CHBO 3-COCOCHzOS02CH3
205-206 dec. CI3H13N0& S:
10.31
10.703.10s
... ...
TI1 VI11 IX
H H H
166-167 dec. C10H7~30 N : 22 69 130-131 CloH6BrN0 Br: 33.56 148-150 C ~ I H ~ ~ N O IS: S 12.66
22.51 3 . 0 7 s 33.36 3 . 0 2 s 12.62 2 . 9 8 s
4.77s
8-COCHK;, 2-COCH2Br 2-COCH20S02CH3
S:
,
..
,
..
...
,
..
...
6.30s 5 . 8 0 ~ 6.25 s 5.78m 6.29s 6.42s 5.82~6 . 3 0 s? 5,80w 6 . 3 7 s? 6.05, 6.09s 5.98s
... ... 7.38s
8.58s ... ... , , . 7.39s 8.60s ,.. ...
7.45s 8.55 s
TABLE I1 MCCICACIDDERIVATIVES RO H H OK.
I I
I
I i I 1
Xco-c--c-c-c-cox
RO OR
H R
X
X XI XI1
CHIC0 CH3C0 CHSCO
CHK2 CH2Br CHzOSOzCHa
180-181 dec. 164-1 66 193-194
XI11
H
CHNz
163-165 dec.
NO.
mp.,
%
C'
calcd.
found
NZX
c=o
C16H&4010 s: 13.14 C1QH20Br2010Br : 30.04 Ci6H26O1&2 s: 11.41
12.95 30.08 11.31
4.72 s
...
5.72 s 5.75 s 5.75s
C ~ H I O S ~ O , N : 21.72
21.30
4.72 s
6.20 s
Formula
oc.
cedures.'g I n addition compounds 1-111 were screened for in vitro cytostatic activity on He-La cell cultures. Results for the indoles are shown in Table 111. All compounds were inactive in vivo at near-toxic doses. In v i t ~ ocytostatic activity was shown only by the bronio ketone I1 a t 1 g./nil. TABLE 111 In Vivo
AND
in Vitro
h C T I V l T Y O F I N D O L E L)XRIVATIVES
50%
No.
I I1
I11 IV V VI VI1 \TI1 IX
Tumor inhib. T/C
He-La inhib., y/ml.
0 0
10
0 0 0 0 0 0 0
1
10
ka,o X 10-4 hf sec.-l ("C.)
2.3(20) 8.9(20) 9.0(50)
.. .. .. .. .. ..
kg,os X 10-4 M sec.-1 ("(2.)
410 (20) KO reaction 3.3(50)
T
with nitrobenzylpyridine, 10-4 .Tf
0.07 0.01 1.10
