Synthesis of two new hydroximinosteroids from cholesterol and their biological evaluation

Abstract

A simple and efficient synthesis of two new hydroximinosteroidal derivatives (11, 13) from cholesterol as starting material was described. The cytotoxicity of these compounds, their intermediates and two other known hydroximinosteroids were evaluated on human cancer cell lines including hepatocellular carcinoma (Hep-G2), cervical cancer (HeLa) and glioblastoma (T98G). Compound 13 presented a potent antiproliferative effect to T98G cancer cell at 2.9 µM of IC₅₀. Our results demonstrated that the compound with oxime group at C-6 having better cytotoxic activity against tested cell lines. Presence of 4,5–double bond or 4,5–epoxide can increase cytotoxicity for the 3,6–dihydroximino derivatives. In addition, the antimicrobial assay showed that two new oximes 11 and 13 were active against E. coli and S. aureus strain (MIC value of 50 µg/mL). The active compounds may provide us a clue for a lead structure of anticancer and antimicrobial agents.