1,16-Diphenyl-19-(4-(4-(2-(trifluoromethyl)phenyl)piperazin-1-yl)butyl)-19-azahexa-cyclo[14.5.1.02,15.03,8.09,14.017,21]docosa-2,3,5,7,8,9,11,13,14-nonaene-18,20,22-trione (9) Yield: 84 %, m.p. 211–212 °C. 1H NMR (DMSO-d 6) δ (ppm): 8.78 (d, 2H, CHarom., J = 8.4 Hz), 8.30 (d, 2H, CHarom., J = 7.8 Hz), 7.74 (t, 2H, CHarom., J = 6.3 Hz), 7.69–7.60 (m, 3H, CHarom.), 7.54 (t, 3H, CHarom., J = 6.3 Hz), 7.48–7.40 CA-4948 nmr (m, 4H, CHarom.), 7.18–7.14 (m, 2H, CHarom.), 4.48 (s, 2H, CH), 3.95–3.91 (m, 3H, CH2), 3.61–3.37 (m, 10H, CH2), 3.22–3.17 (m, 3H, CH2), 3.01–2.92 (m, 4H, CH2). 13C NMR (DMSO-d 6) δ (ppm): 197.19, 173.12, 173.05, 157.51, 147.74, 137.40, 134.36, 133.88, 133.77, 133.43, 133.37, 132.15, 132.10, 132.04, 132.01, 131.99, 131.78 (2C), 131.54, 130.48, 130.13, 129.92, 129.86, 129.71 (2C), 128.53, 128.37, 127.86, 126.66, 126.51, 123.92, 122.45, 122.18, 119.83, 115.34, 115.28, 63.80, 63.78, 61.17, 50.92, 50.68, 48.62, 48.59, 45.44, 45.41, 44.97, 32.76,
31.28, 28.87, 28.73. ESI MS: m/z = 792.2 [M+H]+ find more (100 %). 10-Diphenyl-1H,2H,3H,5H-indeno[1,2-f]isoindole-1,3,5-trione (10) The mixture of 2.06 g (0.006 mol) of 1,3-diphenylcyclopenta[a]indene-2,8-dione (“Indanocyclone”) was Tideglusib suspended in 75 ml of benzene and 0.65 g (0.006 mol) of maleimide was added. After refluxing time of 16 h the yellow residue was evaporated. Next it was purified by column chromatography (chloroform:methanol 9.5:0.5 vol). The combined fractions were condensed to dryness to give 1.50 g (73 %) of (10), m.p. 223–225 °C. 1H NMR (CDCl3) δ (ppm): 7.60 (d, 2H, CHarom., J = 2.7 Hz), 7.59–7.58 (m, 2H, CHarom.), 7.52 (d, 2H, CHarom., J = 2.1 Hz), 7.51–7.49 (m, 2H, CHarom.), 7.45 (d, 2H, CHarom., J = 2.1 Hz), 7.44–7.40 (m, 4H, CHarom.). 13C NMR (CDCl3) δ (ppm): 190.91, 165.89, 165.73, 149.69, 141.97, 139.37,
135.58, 135.52, 135.14, 134.81, 134.24, 131.59, 130.57, 130.54, 129.87, 129.34, 129.28 (2C), 129.09 (3C), 128.59 (2C), 127.91 (2C), 124.59, 124.54. ESI MS: m/z = 424.1 [M+Na]+ (100 %). 2-(4-Bromobutyl)-4,10-diphenyl-1H,2H,3H,5H-indeno[1,2-f]isoindole-1,3,5-trione aminophylline (11) A mixture of imide (10) (2.64 g, 0.006 mol), 1,4-dibromobutane (1.5 ml, 0.012 mol), anhydrous K2CO3 (2.51 g), and catalytic amount of KI were refluxed in acetonitrile for 14 h. Then the solvent was removed on a rotary evaporator and the dark yellow solid residue was purified by column chromatography (chloroform:methanol 9.5:0.5 vol). The combined fractions were condensed to dryness to give 2.44 g (92 %) of (11), m.p. 241–242 °C.