2,3-dihydro-4(1H)- quinazolone derivative and application thereof
A quinazolone and derivative technology, which can be used in drug combinations, cardiovascular system diseases, respiratory system diseases, etc., and can solve the problems of poor tumor curative effect, toxic and side effects, etc.
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Embodiment 1
[0057] Example 1, 2-(4,5-dibromo-2-thienyl)-6-nitro-2,3-dihydroquinazolin-4(1H)-one
[0058]
[0059] step:
[0060] Sequentially weigh 5-nitro-2-aminobenzamide (0.181g, 1mmol) and 4,5-dibromo-2-thiophene aldehyde (0.270g, 1mmol) in a 5mL round bottom flask, add 3mL formic acid, room temperature After stirring, a large amount of yellow solids were precipitated. After 5 minutes, TLC detected that the reaction was complete. Stopped the reaction, filtered the yellow solids, and dried them in vacuum at 40° C. for 6 hours to obtain 0.380 g of yellow solids. The yield was 88%, and the purity by HPLC was 98.29%, m.p. : 261-263°C.
[0061] 1 H NMR (DMSO-d 6, ppm) δ: 9.03 (1H, d, J = 1.2Hz), 8.73 (1H, s), 8.42 (1H, d, J = 2.7Hz), 8.15 (1H, dd, J = 9.0, 3.0Hz), 7.15 (1H, d, J = 0.6Hz), 6.89 (1H, d, J = 9.0Hz), 6.27 (1H, t, J = 2.4Hz)
[0062] EI-MS (m / z): 431 (M +. C 12 h 7 79 Br 2 N 3 o 3 S, 50), 352 (M- 79 Br, 55), 192(80), 165(100), 146(30), 119(30)
Embodiment 2
[0063] Example 2, 2-(4-bromo-2-thienyl)-6-nitro-2,3-dihydroquinazolin-4(1H)-one
[0064]
[0065] The operation steps are the same as in Example 1, yellow solid, m.p.: 243-247°C
[0066] 1 H NMR (DMSO-d 6 , ppm) δ: 8.99 (1H, s), 8.72 (1H, s), 8.42 (1H, d, J=3.0Hz), 8.14 (1H, dd, J=9.0, 2.4Hz), 7.64 (1H, d , J=1.8Hz), 7.16 (1H, d, J=1.2Hz), 6.88 (1H, d, J=9.0Hz), 5.29 (1H, t, J=2.4Hz)
[0067] EI-MS (m / z): 353 (M + .C 12 h 8 79 BrN 3 o 3 S, 100), 323 (M- 79 Br, 80), 274(40), 192(29), 165(85), 146(15), 134(16), 119(25), 90(45)
Embodiment 3
[0068] Example 3, 2-(4-bromo-2-thienyl)-7-chloro-2,3-dihydroquinazolin-4(1H)-one,
[0069]
[0070] step:
[0071] Sequentially weigh 4-chloro-2-aminobenzamide (0.181g, 1mmol) and 4,-bromo-2-thiophene aldehyde (0.270g, 1mmol) in a 5mL round bottom flask, add 5mL of ethanol, stir at room temperature, there is A large amount of white solids precipitated out, and the reaction was stopped after the completion of the reaction by TLC, concentrated under reduced pressure, and subjected to silica gel column chromatography to obtain 0.380 g of white solids with a yield of 88%, m.p.: 201-202°C.
[0072] 1 H NMR (DMSO-d 6 , ppm) δ: 8.67 (1H, s), 7.62 (1H, s), 7.59 (2H, s), 7.12 (1H, s), 6.81 (1H, s), 6.73 (1H, dd, J=8.4, 1.2Hz), 6.06 (1H, s) EI-MS (m / z): 342 (M +. C 12 h 8 79 Br 35 ClN 2 OS, 44), 263 (M- 79 Br, 23), 181(45), 154(100), 126(40)
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