VX-680 Visualization was effected with a SBE-��-CD chemical structure solution of 10 g Ce (SO4)2 and 20 g phosphomolybdic acid in 1 l of 10% H2SO4, followed by heating. Preparative column chromatography was accomplished using silica gel (Kiesel 60, 230–400 mesh; Merck) columns. Proton NMR spectra were recorded on a Bruker AMX 300 instrument at 300 MHz

with acetone-d6 as the solvent and TMS as an internal standard. The infrared (IR) spectra in KBr were recorded on a Mattson IR 300 spectrometer. Synthesis of isoxanthohumol derivatives 7,4′-Di-O-methylisoxanthohumol (4) and 7-O-methylisoxanthohumol selleck kinase inhibitor (5) A mixture of isoxanthohumol (100 mg, 0.282 mmol), anhydrous K2CO3 (232 mg, 1.68 mmol), and methyl iodide (0.5 ml) in 5 ml of anhydrous acetone was stirred for 12 h at room temperature. Acetone was evaporated and the resultant reaction mixture was treated with 10 ml of a saturated NaCl solution and extracted with Et2O (3 × 10 ml). The organic

phase was dried over anhydrous Na2SO4, concentrated and was subjected to column chromatography (CHCl3:MeOH, 99:1) to provide 74.9 mg (69.4%) of light yellow solid (mp = 37–39°C, R f = 0.60, CHCl3:MeOH, 98:2) of 7,4′-di-O-methylisoxanthohumol

(4) and 9.1 mg (8.8%) of white solid (mp = 181–184°C, R f = 0.21, CHCl3:MeOH, 98:2) of 7-O-methylisoxanthohumol (5). 1H NMR and IR spectroscopic data were in agreement with those reported in the literature (Metz and Schwab, 2007; Stevens et Grape seed extract al., 2000). 7-O-n-pentylisoxanthohumol (6) and 7,4′-di-O-n-pentyl-8-isoxanthohumol (7) The reaction was carried out exactly in the same way as it is described for compounds (4 and 5) but 1 ml of n-pentyl iodide was used instead of methyl iodide. The product (33.5 mg, 27.6%) 7-O-n-pentylisoxanthohumol (6) was obtained as a pale yellow solid (mp = 140–142°C, R f = 0.61, CHCl3:MeOH, 97:3). The 1H NMR (300 MHz, acetone-d 6) for compound (6): δ (ppm): 0.93 (t, 3H, J = 7.1 Hz, C-7–O(CH2)4CH3); 1.33–1.54 (m, 4H, C-7–O(CH2)2CH2CH2CH3); 1.61 (d, 6H, J = 1.3 Hz, CH3-4′′ and CH3-5′′); 1.78–1.87 (m, 2H, C7–OCH2CH2(CH2)2CH3); 2.63 (dd, 1H, J = 16.4 Hz, J = 3.0 Hz, CH-3); 2.93 (dd, 1H, J = 16.4 Hz, J = 12.5 Hz, CH-3); 3.26 (d, 2H, J = 7.1 Hz, CH2-1′′); 3.84 (s, 3H, C-5–OCH3); 4.13 (t, 2H, J = 6.3 Hz, C-7–OCH2(CH2)3CH3); 5.16 (t sept, 1H, J = 7.1 Hz, J = 1.3 Hz, CH-2′′); 5.36 (dd, 1H, J = 12.5 Hz, J = 3.0 Hz, CH-2); 6.34 (s, 1H, CH-6); 6.89(d, 2H, J = 8.6 Hz, CH-3′ and CH-5′); 7.38 (d, 2H, J = 8.6 Hz, CH-2′ i CH-6′); 8.53 (s, 1H, C-4′–OH). IR (KBr) cm-1: 2957, 2931, 2856, 1665, 1599, 1570, 1520, 1458, 1262, 1103, 798. C26H32O5 (424.54): calcd.