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A series of androstane derivatives  2–16  were synthesized from 3β-hydroxyandrostan-17-one derivatives ( 1a–e ). Compounds ( 1a,b ) were treated with ethyl cyanoacetate, cyanoacetamide, or malononitrile and gave the corresponding derivatives  2–7 , respectively. Additionally, compounds ( 1a–e ) were condensed with cyanothioacetamide, urea, or guanidine hydrochloride afforded the corresponding derivatives  8–12 , which then by Moffat oxidation gave the oxidized derivatives  9, 11  and  13 , respectively. Finally, compound ( 1 ) condensed with acetyl acetone or ethyl acetoacetate gave cyclohexene derivatives ( 14a–c ) and ( 15a,b ), respectively. Compound  15  was oxidized with a Moffat oxidizing agent and afforded the corresponding oxidized compound  16 . The newly synthesized compounds activated the tumor suppressor p53 in cancer cells through inhibition of the p53-specific ubiquitin E3 ligase HDM2.

Synthesis of androstanopyridine and pyrimidine compounds as novel activators of the tumor suppressor protein p53