[PubMed] [Google Scholar] 4. method from compound 28: NMR (DMSO-= 8.7 Hz), 7.48 (s, 1 H), 7.24 (s, 1 H), 7.10 (d, 2 H, = 8.7 Hz), 7.06 (5, 1 H), 4.58 (s, 2 H), 4.47 (s, 2 H), 4.01 and Rabbit Polyclonal to PPP4R1L 3.86 (each m, 2 H), 1.74 and 1.58 (each m, 2 H), 0.90 (m, 6 H) ppm. The following compounds were synthesized by the above method from structure 14 or 19. 8-[4-[[[[[2-[[[5-(Aminocarbonyl)-3-isothiocyanatophenyl](thiocarbonyl)]amino]ethyl]amino]carbonyl] methyl]oxy]phenyl]-1,3-dipropylxanthine (5c) mp 250 C; NMR (DMSO-= 8.8 Hz), 4.58 (s, 2 H), 4.01 and 3.87 (each m, 2 H), 1.75 and PX-478 HCl 1.58 (each m, 2 H), 0.90 (m, 6 H) ppm. Accurate mass (FAB) consistent with assigned structure. 8-[4-[[[[[2-[[[5-[[[2-(Dimethylamino)ethyl]amino]-carbonyl]-3-isothiocyanatophenyl](thiocarbonyl)]-amino]ethyl]amino]carbonyl]methyl]oxy]phenyl]-1,3-dipropylxanthine (5d) mp 250 C; NMR (DMSO-= 8.6 Hz), 7.85-7.60 (m, 3 H), 7.10 (d, 2 H, = 8.6 Hz), 4.60 (s, 2 H), 4.0 (m, 4 H), 3.85 (m, 4 H), 2.50 (s, 6 H), 1.74 and 1.58 (each m, 2 H), 0.90 (m, 6 H) ppm. 8-[4-[[[[[2-[[[5-[[[2-(Acetylamino)ethyl]amino]carbonyl]-3-isothiocyanatophenyl](thiocarbonyl)]amino]ethyl]amino]carbonyl]methyl]oxy]phenyl]-1,3-dipropylxanthine (5e) mp 250 C; NMR (DMSO-= 8.4 Hz), 7.90 (s, 2 H), 7.80 (s, 1 H), 7.08 (d, 2 H, = 8.4 Hz), 4.50 (s, 2 H), 4.0 (m, 4 H), 3.80 (m, 4 H), PX-478 HCl 1.95 (s, 3 H), 0.90 (m, 6 H); IR 2100 (isothiocyanate), 1680 (C=O), and 1650 cm?1 (C=S). 8-[4-[[[[[2-[[[5-[[[[2-(Dimethylamino)ethyl]amino]-(thiocarbonyl)]amino]-3-isothiocyanatophenyl] (thiocarbonyl)]amino]ethyl]amino]carbonyl]methyl]oxy]-phenyl]-1,3-dipropylxanthine(5f) mp 250 C; NMR (DMSO-= 8.7 Hz), 7.60-7.20(m, 3 H), 7.10 (d, 2 H, = 8.7 Hz), 4.55 (s, 2 H), 4.05 and 3.90 (each m, 2 H), 3.65 (m, 2 H), 2.60 (m, 2 H), 2.30 (s, PX-478 HCl 6 H), 1.75 and 1.60 (each m, 2 H), 0.9 (m, 6 H) ppm. 8-[4-[[[[[2-[[[5-[[[[2-(Acetylamino)ethyl]amino]-(thiocarbonyl)]amino]-3-isothiocyanatophenyl]-(thiocarbonyl)]amino]ethyl]amino]carbonyl]methyl]oxy]phenyl]-1,3-dipropylxanthine (5g) mp 250 C; NMR (DMSO-= 8.7 Hz), 7.55-7.25 (m, 3 H), 7.10 (d, 2 H, = 8.7 Hz), 4.60 (s, 2 H), 4.05 and 3.90 (each m, 2 H), 3.50 (m, 4 H), 1.80 and 1.62 (each m, 2 H), 0.9 (m, 6 H) ppm. 8-[4-[[[[[2-[[[5-[[[2-[[3-(4-Hydroxyphenyl)propionyl]amino]ethyl]amino]carbonyl]-3-isothiocyanatophenyl](thiocarbonyl)]amino]ethyl]amino]carbonyl]methyl]oxy]phenyl]-1,3-dipropylxanthine (5m) XAC (24 mg, 56 mol) and 3-[2-[[[2-[(3,5-diisothiocyanatobenzoyl)amino]ethyl]amino]carbonyl]ethyl]phenol (35 mg, 82 mol) were suspended in 1 mL of dimethylformamide and sonicated until a solution formed. After 1 h, ether was added, and a precipitate formed. The product (5m) was recrystallized from dimethylformamide/ether to give 39.9 mg (83% yield): NMR (DMSO-= 8.6 Hz, 8-phenyl ring, meta to ether), 7.75 (m, 1 H, NH), 7.95, 7.77, and 7.58 (each s, 1 H, 2,4,6-aryl protons), 7.10 (d, 2 H, = 8.6 Hz, 8-phenyl ring, ortho to ether), 6.96 (d, 2 H, = 8.3 Hz, meta to phenol), 6.63 (d, 2 H, = 8.3 Hz, ortho to phenol), 4.58 (s, 2 H, C956.8 (M + H + 2 Na), 924.8 (M + PX-478 HCl H + Na), 505.1, 447.2, and 389.2. 8-[4-[[[[[2-[[(3,5-Diisothiocyanatophenyl)(thiocarbonyl)]amino]ethyl]amino]carbonyl]methyl]oxy]-phenyl]-1,3-dipropylxanthine (22) was synthesized by the above method from compound 21: mp 250 C; NMR (DMSO-= 8.5 Hz), 7.46 (s, 2 H), 7.24 (s, 1 H), 7.09 (d, 2 H, = 8.5 Hz), 4.58 (s, 2 H), 4.01 (m, 2 H), 3.87 (m, 2 H), 1.74 (m, 2 H), 1.58 (m, 2 H), 0.90 (m, 6 H) ppm. Accurate mass (FAB) consistent with the assigned.