Synthesis and cytotoxic evaluation of four new 6E-hydroximinosteroids

• 6E-hydroximinosteroids were synthesized from the corresponding ketones.
• Cytotoxic activity of the compounds was evaluated against PC-3 and LNCaP.
• The biological activity was compared to that of sulfated polyhydroxysteroid analogs.
• 2β,3α,6β-sulfated steroid showed the highest cytotoxicity against LNCaP.

Four new 6E-hydroximinosteroids (1, 2a, 3 and 4) have been synthesized from the corresponding ketones, 2β,3β-dihydroxy-5α-cholestan-6-one (5), 2α,3α-dihydroxy-5α-cholestan-6-one (6), 2β,3α-dihydroxy-5α-cholestan-6-one (7) and 2β,3α-dihydroxy-5α-cholestan-6-one-disulfate (8). The cytotoxic activity of the steroidal oximes was evaluated against two prostate carcinoma cell lines (PC-3 and LNCaP) and compared with that of five polyhydroxylated sulfated analogs (8–12). Oxime 3 and trisulfated analog 11 were the most active compounds with IC50 values of 10.8 μM (PC-3) and 7.9 μM (LNCaP), respectively.

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