Abstract
A series of substituted androstanopyridine derivatives
2–5
were synthesized using 17-acetyl- 1,7,8,10,11,12,13,15,16,17-decahydro-10,13-dimethyl-2H-cyclopenta[a]-phenanthren-3(6
H
,9
H
,14
H
)-one (progesterone,
1
) as a starting material. Reaction of
1a–1d
with malononitrile and aldehydes in the presence of ammonium acetate gave the corresponding amino cyanopyridine derivatives
2a–2d
. The same compounds
1a–1d
reacted with cyanoacetamide and aldehydes in the presence of ammonium acetate to give a mixture of
3a–3d
and
4a–4d
, that was separated chromatographically. The reaction of compounds
1a–1d
with ethyl cyanoacetate and aldehydes led to products
5a–5d
. Structures of the newly synthesized compounds were elucidated by physical and spectral methods. The synthesized compounds were tested as 5α-reductase inhibitors and anti-prostate cancer agents.