N-ALKYLPHTHALIMIDES : STRUCTURAL REQUIREMENT OF THALIDOMIDAL ACTION ON 12-0-TETRADECANOYLPHORBOL-13-ACETATE-INDUCED TUMOR NECROSIS FACTOR α PRODUCTION BY HUMAN LEUKEMIA HL-60 CELLS

Abstract

Phthalimide analogs N-substituted with n-butyl, (tert)___--butyl, hexyl and adamantyl groups were designed and prepared as simplified analogs of thalidomide and methylthalidomide. All the compounds prepared except N-n-butylphthalimide showed thalidomidal activity on 12-0-tetradecanoylphorbol-13-acetate-induced tumor necrosis factor (TNF)-α production by human leukemia HL-60 cells. Among the investigated compounds, including thalidomide and methylthalidomide, N-adamantylphthalimide showed the most potent TNF-α production-enhancing activity.