Abstract
An eco friendly and efficient method for the synthesis of 1,8-dioxooctahydroxanthene derivatives in excellent yield (∼90%) using ionic liquids 1-butyl-3-methylimidazoliumtetrafluoroborate (BMIF), 1-butyl-3-methylimidazoliumbromide (BMIB) and 1-butyl-3-methylimidazoliumchloride (BMIC) under solvent free condition has been developed for the first time. All the synthesized compounds (3a-3k) were fully characterized by analysis of spectral data (FT-IR, 1H NMR, 13C NMR, UV–Vis and mass spectroscopy). Quantum chemical studies were also done for one of the synthesized compound, 3,3,6,6-tetramethyl-9-(2,3,4-trimethoxyphenyl)-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione (3a). All the synthesized compounds (3a-3k) were assayed for in vitro antitumor activities against human lung cancer cell line (A549). In cell proliferation experiments, 9-(3,4-dimethoxyphenyl)-3,3,6,6-tetramethyl-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione (3k) was found to be most potent agent and significantly inhibited the tested cancer cell line A549 (IC50 3.88) with 88.77% inhibiton at 10 mM concentration.
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