Light-promoted stereoselective late-stage difunctionalization and anti-tumor activity of oridonin
Qianhui Tang1, Yougan Lu1, Junying Song1
1School of Life Science and Engineering, Southwest Jiaotong University, No. 111, Erhuan Rd, Chengdu 610031, PR China.
Abstract:
The late-stage difunctionalization of diterpene oridonin by light-promoted direct oxyamination with various O-benzoylhydroxylamines was carried out to afford C16α-N-C17-OBz-oridonin derivatives (1-25) for the first time. Though as a radical reaction, it features high stereoselectivity to only produce C16α-N-C17-OBz-oridonins. The in vitro antiproliferative activity of these C16α-N-C17-OBz-oridonins against the human breast cancer cell lines (MCF-7) was evaluated by MTT assay, showing that most of the synthesized compounds possessed moderate anticancer activity against MCF-7 cell lines superior or similar to the parent compound oridonin. The derivative 25 with a N-methyl-N-(naphthalen-1-ylmethyl) substitution showed better cytotoxicity against MCF-7 cells (IC50 value of 11.75 μM) than oridonin (IC50 value of 17.95 μM).
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