Abstract
A series of androstane derivatives
were synthesized from 3β-hydroxyandrostan-17-one derivatives (
). Compounds (
) were treated with ethyl cyanoacetate, cyanoacetamide, or malononitrile and gave the corresponding derivatives
, respectively. Additionally, compounds (
) were condensed with cyanothioacetamide, urea, or guanidine hydrochloride afforded the corresponding derivatives
, which then by Moffat oxidation gave the oxidized derivatives
and
, respectively. Finally, compound (
) condensed with acetyl acetone or ethyl acetoacetate gave cyclohexene derivatives (
) and (
), respectively. Compound
was oxidized with a Moffat oxidizing agent and afforded the corresponding oxidized compound
. The newly synthesized compounds activated the tumor suppressor p53 in cancer cells through inhibition of the p53-specific ubiquitin E3 ligase HDM2.