Multicomponent assembly of novel antiproliferative steroidal dihydropyridinyl spirooxindoles

• Multicomponent assembly of steroidal dihydropyridinyl spirooxindoles is described.
• The protocol formed two C–C bonds, two C–N bonds, and an all-carbon quaternary stereogenic center in a single operation.
• Some of these compounds were more potent than 5-FU.
• Compound 5o represented excellent inhibitory effect toward EC-109 (IC50 = 0.32 μM).

Multicomponent assembly of steroidal dihydropyridinyl spirooxindoles from pregnenolone, isatins, malononitrile, and ammonium acetate is described, which involves the formation of two C–C bonds, two C–N bonds, and an all-carbon quaternary stereogenic center in a single operation. MTT assays showed that some of these compounds had moderate to excellent cytotoxicity against the tested cancer cell lines and were more potent than 5-FU. Particularly, compound 5o represented excellent inhibitory effect toward EC-109 (IC50 = 0.3 μM), being about 33-fold more potent than 5-FU.

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