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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Multicomponent assembly of novel antiproliferative steroidal dihydropyridinyl spirooxindoles
Yan-Ling Zhang1, Ya-Fei Li2, Jun-Wei Wang2
1School of Pharmaceutical Sciences of Zhengzhou University and Collaborative Innovation Center of New Drug Research and Safety Evaluation, Zhengzhou 450001, PR China; College of Chemistry and Chemical Engineering, Xuchang University, Xuchang 461000, PR China.
Abstract:
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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