The crude A07 was obtained by filtration and then purified by column chromatography on silica (dichloromethane:methanol = 15:1) to afford the prospective compound A07 like a light yellow solid (0.06 g, yield 59.23%). = 7.4 Hz, 1H), 7.00 (t, = 7.5 Hz, 1H), 6.81 (d, = 7.2 Hz, 1H), 6.63 (t, = 7.3 Hz, 1H), 4.97 (s, 2H); 13C-NMR (DMSO-d6) : 164.9, 160.1, 157.7, 155.5, 154.1, 144.1, 143.4, 139.8, 137.0, 135.7, 134.8, 131.2, 128.4(2C), 127.6(2C), 127.0, 126.7, 125.9, 125.0, 124.9, 123.3, 116.3, 116.2, 115.3, 115.1;LC-MS (A07) Intermediate 6 (0.1 g, 0.27 mmol) was placed in a 250 mL pear-shaped flask and dissolved with 120 mL of methanol. The combination was stirred for 5 min at 0 C and then the pH was modified to 11 by adding 2 M NaOH aqueous remedy. Then 5 mL aqueous hydroxylamine remedy (50%) was added and the reaction was allowed to warm to space temperature. After the reaction was total, as monitored by TLC, the combination was partially evaporated and the pH of the residue was modified to 6 by adding 10% aqueous hydrochloric acid remedy. The crude A07 was acquired by filtration and then purified by column chromatography on silica (dichloromethane:methanol = 15:1) to afford the target compound A07 like a light yellow solid (0.06 g, yield 59.23%). Mp: 249.0C251.8 C; 1H-NMR (DMSO-d6) : 11.41 (s, 1H), 10.20 (s, 1H), 9.14 (s, 1H), 8.63 (d, = 8.2 Hz, 2H), 8.62 (s, 1H), 8.59 (d, = 8.8 Hz, 1H), 8.29 (d, = 8.8 Hz, 1H), 8.00C7.98 (m, 2H), 7.95 (d, = 8.2 Hz, 2H), 7.30C7.28 (m, 2H); 13C-NMR (DMSO-d6) : 163.6, 160.0, 157.6, 155.4, 154.1, 144.1, 139.6, 136.9, 134.8, 133.9, 131.1, 127.7 (2C), 127.4 (2C), 125.8, 124.9, 124.8, 115.3, 115.1; LC-MS (7) A mixture of (4-acetylphenyl)boronic acid(0.10 g, 0.67 mmol), malonate (0.21 g, 0.20 mmol) and pyridine (0.053 g, 0.67 mmol) in dry toluene (10 mL) was stirred at reflux for 2 h. After the reaction was total as indicated by TLC, the combination was cooled to space temp and poured into water. The pH of the combination was adjust to 5 by adding 10% aqueous hydrochloric acid solution and then it was filtered to give intermediate 7 like a white solid (0.16 g, yield 80.73%). (8) Intermediate 8 was prepared from intermediate 7 using the same reaction conditions explained above for making intermediate 5. Light yellow solid, yield 90.0%. (9) Intermediate 9 was prepared from intermediate 8 using the same reaction conditions explained above for making intermediate 6. Light yellow Rabbit Polyclonal to Connexin 43 solid, yield 80.8%. (A02) Compound A02 was prepared from intermediate 8 using the same reaction conditions explained above for making compound A01. Light yellow solid, yield MC1568 54.05%. Mp: 263.8C265.5 C; 1H-NMR (DMSO-d6) : 10.18 (s, 1H), 9.46 (s, 1H), 8.63 (d, = 8.0 Hz, 2H), 8.62 (s, 1H), 8.58 (d, = 8.8 Hz, 1H), 8.28 (d, = 8.8 Hz, MC1568 1H), 8.02C8.00 (m, 2H), 7.82 (d, = 8.0 Hz, 2H), 7.67 (d, = 15.7 Hz, 1H), 7.37 (d, = 7.8 Hz, 1H), 7.31C7.28 (m, 2H), 7.05 (d, = 15.7 Hz, 1H), 6.94 (t, = 7.5 Hz, 1H), 6.77 (d, = 7.9 Hz, 1H), 6.60 (t, = 7.5 Hz, 1H), 4.98 (s, 2H); 13C-NMR (DMSO-d6) : 163.4, 160.0, 157.5, 155.2, 154.3, 143.9, 141.7, 138.9, 138.1, 136.8, 136.5, 134.8, 131.1, 128.3(2C), 128.1(2C), 125.9, 125.6, 124.8, 124.7, 124.7, 123.5, 123.4, 116.3, 116.1, 115.2, 115.0; LC-MS (A08) Compound A08 was prepared from intermediate 9 using the same reaction conditions explained above for making compound A07. Light yellow solid, yield 58.00%. Mp: 178.1C180.0 C; 1H-NMR (DMSO-d6) : 10.80 (s, 1H), 10.16 (s, 1H), 9.16 (s, 1H), 8.62 (s, 1H), 8.58 (d, = 8.2 Hz, 2H), 8.57 (d, = 8.8 Hz, 1H), 8.27 (d, = 8.8 Hz, 1H), 8.01C7.99 (m, 2H), 7.75 (d, = 8.2 Hz, 2H), 7.56 (d, = 15.5 Hz, 1H), 7.30C7.27 (m, 2H), 6.61 (d, = 15.5 MC1568 Hz, 1H); 13C-NMR (DMSO-d6) : 162.6, 160.0, 157.5, 155.2, 154.3, 144.0, 137.9, 137.5, 136.8, 136.5, 134.8, 131.1, 128.2(2C), 128.0(2C), 125.6, 124.8, 124.7, 120.3, 115.3, 115.1; LC-MS (10) A mixture of intermediate 4.The absorbance at 570 nm was measured in the 96-well plate reader. 8.8 Hz, 1H), 8.19 (d, = 8.2 Hz, 2H), 8.01C8.00 (m, 2H), 7.31C7.28 (m, 2H), 7.22 (d, = 7.4 Hz, 1H), 7.00 (t, = 7.5 Hz, 1H), 6.81 (d, = 7.2 Hz, 1H), 6.63 (t, = 7.3 Hz, 1H), 4.97 (s, 2H); 13C-NMR (DMSO-d6) : 164.9, 160.1, 157.7, 155.5, 154.1, 144.1, 143.4, 139.8, 137.0, 135.7, 134.8, 131.2, 128.4(2C), 127.6(2C), 127.0, 126.7, 125.9, 125.0, 124.9, 123.3, 116.3, 116.2, 115.3, 115.1;LC-MS (A07) Intermediate 6 (0.1 g, 0.27 mmol) was placed in a 250 mL pear-shaped flask and dissolved with 120 mL of methanol. The combination was stirred for 5 min at 0 C and then the pH was modified to 11 by adding 2 M NaOH aqueous remedy. Then 5 mL aqueous hydroxylamine remedy (50%) was added and the MC1568 reaction was allowed to warm to space temperature. After the reaction was total, as monitored by TLC, the combination was partially evaporated and the pH of the residue was modified to 6 by adding 10% aqueous hydrochloric acid remedy. The crude A07 was acquired by filtration and then purified by column chromatography on silica (dichloromethane:methanol = 15:1) to afford the target compound A07 like a light yellow solid (0.06 g, yield 59.23%). Mp: 249.0C251.8 C; 1H-NMR (DMSO-d6) : 11.41 (s, 1H), 10.20 (s, 1H), 9.14 (s, 1H), 8.63 (d, = 8.2 Hz, 2H), 8.62 (s, 1H), 8.59 (d, = 8.8 Hz, 1H), 8.29 (d, = 8.8 Hz, 1H), 8.00C7.98 (m, 2H), 7.95 (d, = 8.2 Hz, 2H), 7.30C7.28 (m, 2H); 13C-NMR (DMSO-d6) : 163.6, 160.0, 157.6, 155.4, 154.1, 144.1, 139.6, 136.9, 134.8, 133.9, 131.1, 127.7 (2C), 127.4 (2C), 125.8, 124.9, 124.8, 115.3, 115.1; LC-MS (7) A mixture of (4-acetylphenyl)boronic acid(0.10 g, 0.67 mmol), malonate (0.21 g, 0.20 mmol) and pyridine (0.053 g, 0.67 mmol) in dry toluene (10 mL) was stirred at reflux for 2 h. After the reaction was total as indicated by TLC, the combination was cooled to space temp and poured into water. The pH of the combination was adjust to 5 by adding 10% aqueous hydrochloric acid solution and then it was filtered to give intermediate 7 like a white solid (0.16 g, yield 80.73%). (8) Intermediate 8 was prepared from intermediate 7 using the same reaction conditions explained above for making intermediate 5. Light yellow solid, yield 90.0%. (9) Intermediate 9 was prepared from intermediate 8 using the same reaction conditions explained above for making intermediate 6. Light yellow solid, yield 80.8%. (A02) Compound A02 was prepared from intermediate 8 using the same reaction conditions explained above for making compound A01. Light yellow solid, yield 54.05%. Mp: 263.8C265.5 C; 1H-NMR (DMSO-d6) : 10.18 (s, 1H), 9.46 (s, 1H), 8.63 (d, = 8.0 Hz, 2H), 8.62 (s, 1H), 8.58 (d, = 8.8 Hz, 1H), 8.28 (d, = 8.8 Hz, 1H), 8.02C8.00 (m, 2H), 7.82 (d, = 8.0 Hz, 2H), 7.67 (d, = 15.7 Hz, 1H), 7.37 (d, = 7.8 Hz, 1H), 7.31C7.28 (m, 2H), 7.05 (d, = 15.7 Hz, 1H), 6.94 (t, = 7.5 Hz, 1H), 6.77 (d, = 7.9 Hz, 1H), 6.60 (t, = 7.5 Hz, 1H), 4.98 (s, 2H); 13C-NMR (DMSO-d6) : 163.4, 160.0, 157.5, 155.2, 154.3, 143.9, 141.7, 138.9, 138.1, 136.8, 136.5, 134.8, 131.1, 128.3(2C), 128.1(2C), 125.9, 125.6, 124.8, 124.7, 124.7, 123.5, 123.4, 116.3, 116.1, 115.2, 115.0; LC-MS (A08) Compound A08 was prepared from intermediate 9 using the same reaction conditions explained above for making compound A07. Light yellow solid, yield MC1568 58.00%. Mp: 178.1C180.0 C; 1H-NMR (DMSO-d6) : 10.80 (s, 1H), 10.16 (s, 1H), 9.16 (s, 1H), 8.62 (s, 1H), 8.58 (d, = 8.2 Hz, 2H), 8.57 (d, = 8.8 Hz, 1H), 8.27 (d, = 8.8 Hz, 1H), 8.01C7.99 (m, 2H), 7.75 (d, = 8.2 Hz, 2H), 7.56 (d, = 15.5 Hz, 1H), 7.30C7.27 (m, 2H), 6.61 (d, = 15.5.