A pyrano[2,3-b]quinoline derivative, its preparation method and its application in antitumor
A 3-b, derivative technology, applied in the direction of antineoplastic drugs, drug combinations, organic chemistry, etc., can solve the problem that the synthetic raw materials are not easy to obtain, and achieve a good effect of inhibiting proliferation in vitro
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[0025] In the preparation method of the present invention, the molar ratio of the compound of formula II, malononitrile, 4-hydroxyquinolin-2-one and catalyst is 1:1:1:0.1-0.6.
[0026] In the preparation method of the present invention, the solvent used is one of ethanol, toluene, tetrahydrofuran, ethylene glycol, N,N-dimethylformamide, water or acetonitrile.
[0027] In the preparation method of the present invention, the catalyst used can be a base, an acid, or a small organic molecule catalyst; the base is one of sodium hydroxide, sodium carbonate, cesium carbonate or hexahydropyridine, The acid is one of p-toluenesulfonic acid or acetic acid, and the small organic molecule catalyst is L-proline.
[0028] More specifically, the reaction temperature of the preparation method of the present invention is 80-110° C., and the reaction time is 20-50 minutes.
[0029] Through the screening of multiple reaction conditions, and considering the effect of the reaction and the princip...
Embodiment 1
[0032] Add 2-chloroquinoline-3-carbaldehyde (0.2mmol), malononitrile (0.2mmol) and 4-hydroxyquinolin-2-one (0.2mmol) into a 5mL microwave reaction tube, then add L-proline (0.1mmol) and ethanol 2mL, the reaction tube was sealed, stirred for 10 seconds in advance, and the mixture was reacted at 100°C for 30 minutes under microwave radiation. After the reaction was completed, the reaction system was cooled to room temperature, and the solid was precipitated. Recrystallization with a mixed solvent of DMF and water gave 2-(6-oxo-6,7-dihydro-5H-pyrano[2,3-b:5,6-c']bisquinoline-7 -yl) malononitrile (Ia): Yield 70%; m.p.:>300℃; IR(KBr,ν,cm- 1 ):2964,2185,1654,1613,1578,1421,1397,1344,1326,1255,1180,1151,1110,795; 1 H NMR (400MHz, DMSO-d 6 )(δ,ppm):12.23(s,1H,NH),8.82(s,1H,ArH),8.14-8.11(m,2H,ArH),8.03(d,J=8.4Hz,1H,ArH), 7.90(t, J=8.4Hz, 1H, ArH), 7.72-7.65(m, 2H, ArH), 7.46(d, J=8.0Hz, 1H, ArH), 7.40(t, J=7.6Hz, 1H, ArH), 5.41(d, J=3.6Hz, 1H, CH), 5.29(d, J=3.6Hz, 1H, CH). 13 ...
Embodiment 2
[0034] According to the method for Example 1, 2-chloroquinoline-3-formaldehyde is replaced with 6-tert-butyl-2-chloroquinoline-3-formaldehyde, and L-proline is used as a catalyst to react under microwave radiation for 30 minutes, After the reaction, the reaction system was cooled to room temperature, and after the solid was precipitated, suction filtration was performed, and the target product 2-(10-tert-butyl-6-oxo-6,7-di Hydrogen-5H-pyrano[2,3-b:5,6-c']bisquinolin-7-yl)malononitrile (Ib): Yield 68%; m.p.:>300℃; IR(KBr,ν,cm- 1 ):2963,2185,1653,1609,1576,1504,1435,1328,1262,1241,1185,1094,1029,928,897,829,750; 1 H NMR (400MHz, DMSO-d 6 )(δ,ppm):12.26(s,1H,NH),8.80(s,1H,ArH),8.15(d,J=7.6Hz,1H,ArH),8.07-7.98(m,3H,ArH), 7.76-7.72(m,1H,ArH),7.50-7.41(m,2H,ArH),5.42(d,J=3.2Hz,1H,CH),5.30(d,J=3.2Hz,1H,CH), 1.45(s,9H,(CH 3 ) 3 C). 13 C NMR (100MHz, DMSO-d 6 )(δ,ppm):161.1,156.3,154.7,149.6,144.6,141.0,138.9,132.8,131.1,127.6,126.9,123.3,123.2,122.8,116.3,113.6,113.0,112.7,10...
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