E,E-2-Benzylidene-6-(nitrobenzylidene)cyclohexanones: Syntheses, cytotoxicity and an examination of some of their electronic, steric, and hydrophobic properties

Three series of structurally isomeric 2-benzylidene-6-(nitrobenzylidene) cyclohexanones 1–3 were prepared and evaluated against human Molt/C8 and CEM T-lymphocytes as well as murine L1210 cells. The IC50 values of the majority of compounds are less than 10 μM and in some assays, the figures for 1d and 1e are submicromolar. Correlations were discerned between cytotoxic potencies and the atomic charges on one of the olefinic carbon atoms, the torsion angles between an aryl ring, and the adjacent unsaturated group as well as log P values. Three representative compounds were examined for their effect on respiration in rat liver mitochondria.

Three series of nitro compounds 1–3 were evaluated for cytotoxicity. The variation in potencies was explored by measuring the atomic charges on carbon atoms CA and CB, the torsion angle θA and θB, log P values and respiration in rat liver mitochondria.Figure optionsDownload as PowerPoint slide