Yield,
111,.
Colllyd
I I1 I11 I \. \-I \-I1 '[ From I \-.
C
62.8s 6 2 , SX 6" 7 2 67,92 62. i 2 64,65 64.10
63.3 63.2 sx ,3" S5.8 72.7 73.4
110
\
7---
1%
106-1 UT 130-132 h3-84 104- 103 142 113-1 17
i9.6
I I1 1111 I \.
Okt ~\l,,i,le
~Lse~cIiiii~
Illy
I bard
band
... ...
16!)2 (s) 1604 ( 5 ) 3685 (s)
... ...
3415 (m) 2778,5,286.i( 1 i o % (>) ... \* 2 i O . 7, 276 5 I713 ( c ) 3500 (111) \ .I 26X. 7 , 2 i 5 , 3 1716 ( 3 ) 34.50 (m) \.I I 269. I , 2x5, S 1717 (s) 3,512 (m) tk Ultraviolet spectra were determined iii alcoholic sollition with a CF4 Optic Milano spectrophotometer. Infrared spectra were determined on a U.R.10 Zeias Jena DDR spectrophotometer hmax 280 my for estradiol. in KBr disks. 2 S 2 . 3 , 28s
::.OB 3.1s 2.64 3 . IS 3 01 2.0s
6.1)s 7.04
6.6s 7.47
c
H
h-
62.50 62.SO 62.91 67.85
S , 20
3 , 04 2.0s Zl4 2.56 3 . 1s 3.02 2.97
62.64
64.85 63.98
5.08 i.15
7.03 6 ,!)*5 0.77 7.43
('1
1.5 5!l 1551 16,0!1 13.20 1 6 ,20 15.27 l5,3!)
20yGirihibition.
Infrared spectra," c1i1-1
V l t r a \ iulet ( ',,!L,ld
8 ox S.0 S 7.04
l ~ i J l l l l d ,;c,
c1 I 3 60 15.50 16.12 12 . 39 16.13 15.30 15.16
(lay. Crldcr these c*oiiditioiisVI caused 60% :~ncl
TIBLEI1 s p E C ~ ~ ~ ~ C )rl.i.r.1 S ( ~ O 1 ~C~~ ~~ . W ~ ) ~ .I-\X N~)S
SlJCL!t ril,'
v-N 3.00
--Calcd. €I
CHO, u ~ 1735 = ~ cm-'. The position of OH group stretvhirig baritls in the range of 3320-3400 mi-' alio iupports the Structures attributed by US to the deiivativcs I-TII. ho~vrii t i Tablc 11, the ult raviolet spectra :ilso peri i i i t t he diffeientiation between 3 - arid 17-substituted deriratives of estrogens, ab the S,S-bis(khloroethy1)cwbamoyl group in the 3 position causes a coristaiit shift of about 10 nip toward shorter wavelengths. Biological Activity.-The antitumor activity of androsterone derivatives I and I1 is shown in Table 111. Tho wtivity of t h c (+trog(lti tlcrivzt ives w:ic:tcitC(1 0 1 1 mts bearing Walker 2.56 carcino6arconia (doses of 50 ing/l
