Scopoletin derivatives with anti-tumor activity, and preparation method and application thereof
A tumor and drug technology, applied in the field of scopolamine derivatives, can solve the problems of unstable metabolism, high effective concentration, and short action time in the body
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Embodiment 1
[0048] Preparation of 2,4-dihydroxy-5-methoxybenzaldehyde:
[0049] Add aluminum trichloride (80g, 0.60mol) and anhydrous dichloromethane (400mL) into a 1000mL three-necked flask, then add 1gCTAB, and stir. 2,4,5-Trimethoxybenzaldehyde (20g, 0.10mol) was dissolved in anhydrous dichloromethane (100mL), added dropwise to the reaction flask, and heated to reflux for 4h. Pour the reactant into 500 g of crushed ice to which 100 mL of concentrated hydrochloric acid has been added, stir for 0.5 h, separate the organic layer, wash the organic layer three times with saturated aqueous sodium chloride solution, dry over anhydrous sodium sulfate, evaporate the solvent by rotary evaporation, and recrystallize from toluene , to obtain a light yellow solid (15.50g, 90.42%), mp.145℃.
[0050] 1 H NMR (300MHz, DMSO-d 6 ):δ3.71(3H,s,OCH 3 ), 3.94 (1H, s, OH), 6.50 (1H, s, phenyl1-H), 6.69 (1H, s, phenyl1-H), 9.80 (1H, s, OH), 10.70 (1H, s, CHO) .ESI-MS(m / z):168[M-H] - .
[0051] Preparat...
Embodiment 2
[0063] 3-(4-Chlorophenyl)-N-(6-methoxy-7-hydroxy-2H-1-benzopyran-2-one-3-yl)acrylamide (Ⅰ 2 )
[0064] Referring to the preparation method of Example 1, using p-chlorocinnamic acid and 6-methoxy-7-hydroxy-3-aminocoumarin as raw materials, recrystallized from ethanol to obtain about 120mg, yellow-white powder, yield 81.4%, mp >250°C.
[0065] ESI-MS(m / z):366[M-H]-.
[0066] IR(KBr,cm -1 ):3334(OH);3120(C=C);1708,1677(C=O).
[0067] 1 H NMR (DMSO-d 6 , 300MHz) δ: 3.83 (3H, m, OCH 3 ), 6.81 (1H, s, H8), 7.28 (1H, d, J=13.8Hz, CH), 7.35 (2H, d, J=8.1Hz, Ar-H), 7.51 (1H, s, H5), 7.53(2H,d,J=8.1Hz,Ar-H),7.64(1H,d,J=13.8Hz,CH),8.73(1H,s,H4),9.76(1H,s,NH),10.10( 1H,s,OH).
Embodiment 3
[0069] 3-(4-fluorophenyl)-N-(6-methoxy-7-hydroxy-2H-1-benzopyran-2-one-3-yl)acrylamide (Ⅰ 3 )
[0070] Referring to the preparation method of Example 1, using p-fluorocinnamic acid and 6-methoxy-7-hydroxy-3-aminocoumarin as raw materials, recrystallized from ethanol to obtain about 125mg, yellow powder, yield 75.2%, mp> 250°C.
[0071] ESI-MS(m / z):354[M-H] - .
[0072] IR(KBr,cm -1 ):3331(OH);3144(C=C);1710,1673(C=O).
[0073] 1 H NMR (DMSO-d 6 , 300MHz) δ: 3.83 (3H, m, OCH 3 ), 6.81 (1H, s, H8), 7.23 (1H, d, J=13.8Hz, CH), 7.32 (2H, d, J=8.1Hz, Ar-H), 7.49 (1H, s, H5), 7.54(2H,d,J=8.1Hz,Ar-H),7.67(1H,d,J=13.8Hz,CH),8.86(1H,s,H4),9.84(1H,s,NH),10.17( 1H,s,OH).
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