Abstract
Synthesis of seven semi-synthetic analogs of NDGA is described. An approach to NDGA derivatization is described in which the ortho-phenolic groups are tethered together by one atom, forming a 5-membered heterocyclic ring. The analogs were evaluated for cytotoxicity in four cancer cell lines and compared to NDGA and tetra- O-methyl-NDGA (M4N) ( 1a). NDGA bis-cyclic sulfate ( 2a), NDGA bis-cyclic carbonate ( 2b), and methylenedioxyphenyl-NDGA ( 2d) and NDGA tetra acetate ( 1b) showed anti-cancer activity in vitro. Two compounds, ( 1b) and ( 2b), were evaluated for anticancer activity in a mouse xenograft model of human melanoma and showed dose-dependent activity.
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