N-Alkylphthalimides: structural requirement of thalidomidal action on 12-O-tetradecanoylphorbol-13-acetate-induced tumor necrosis factor alpha production by human leukemia HL-60 cells.
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-O-tetradecanoylphorbol-13-acetate-induced tumor necrosis factor (TNF)-alpha production by human leukemia HL-60 cells. Among the investigated compounds, including thalidomide and methylthalidomide, N-adamantylphthalimide showed the most potent TNF-alpha production-enhancing activity.
Shibata
Y
Y
Institute of Molecular and Cellular Biosciences, University of Tokyo, Japan.
Shichita
M
M
Sasaki
K
K
Nishimura
K
K
Hashimoto
Y
Y
Iwasaki
S
S
D006801:Humans; D007938:Leukemia / Q000378:metabolism / Q000473:pathology; D010797:Phthalimides / Q000737:chemistry / Q000494:pharmacology*; D013755:Tetradecanoylphorbol Acetate / Q000494:pharmacology*; D014407:Tumor Cells, Cultured; D014409:Tumor Necrosis Factor-alpha / Q000096:biosynthesis*
D010797:Phthalimides; D014409:Tumor Necrosis Factor-alpha; D013755:Tetradecanoylphorbol Acetate