Preparation of coumarin derivative and application of coumarin derivative to control of serious cerebral disease
A technology for diseases and drugs, applied in the field of medicine, can solve problems such as side effects and insufficient curative effect
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Embodiment 1
[0106] 3-(4-Acetylpiperazin-1-yl)-5,7-dihydroxy-4-methyl-2H-chromen-2-one (5A, R=methyl)
[0107]
[0108] According to Reaction Formula 1, dissolve anhydrous piperazine 1 (0.10mol) and 0.10mol baked potassium carbonate in anhydrous acetonitrile, and slowly add 0.10mol 2 of anhydrous acetonitrile solution dropwise under vigorous stirring at room temperature, the reaction solution changes from milky white to Gradually changed to pale yellow, followed by LC-MS monitoring, after the reaction was completed, potassium carbonate was filtered off, acetonitrile was spun off, the resulting residue was added with water, stirred for 30 min, extracted three times with EA, combined extracts were dried over anhydrous Na2SO4 for 5 hours. Filter to remove Na2SO4, and distill the filtrate to remove the solvent under reduced pressure to obtain brown-red oil 3, which is directly used in the next reaction without purification.
[0109] Mix and dissolve phloroglucinol (0.10mol) and 3 (0.10mol) ...
Embodiment 2
[0113] 5,7-Dihydroxy-4-methyl-3-(4-(2,2,2-trifluoroacetyl)piperazin-1-yl)-2H-benzopyran-2-one (5B, R=trifluoromethyl)
[0114]
[0115] According to Reaction Formula 1, 4 (27.6mg, 0.1mmol) was dissolved in anhydrous THF, and trifluoroacetic anhydride (0.10mmol) was added for reaction to give 5B as a pale yellow solid with a yield of 88.0%, m.p.274-275°C.
[0116] 1 H NMR (300MHz, DMSO-d 6 ):δ10.457(s,1H),10.220(s,1H),6.258(d,1H,J=1.8Hz),6.127(d,1H,J=1.8Hz),3.314-4.500(m,4H) ,2.800-3.310(m,4H),2.659(s,3H); 13 C NMR (125MHz, DMSO-d 6 ):δ160.323,158.034,157.942,154.540,150.314,127.565,117.495,115.207,102.131,99.354,94.136,49.441,48.731,46.183,43.711,16.995 HR Calcd.For CMS; 16 h 16 f 3 N 2 o 5 (M+H + )373.1011; found 373.1012.
Embodiment 3
[0118] N-Butyl-4-(5,7-dihydroxy-4-methyl-2-oxo-2H-benzopyran-3-yl)piperazine-1-amide (7A, R=n-butyl)
[0119]
[0120] According to Reaction Formula 1, dissolve 4 (0.1mmol) in anhydrous THF, add a small amount of DMF to aid in dissolution, add n-butyl isothiocyanate (0.12mmol), react at 50°C, and track and monitor with LC-MS. After the reaction is completed, evaporate Except for THF and DMF, the product was purified by silica gel column chromatography, the eluent was PE:EA=1:2, and the title compound was obtained as an off-white powder with a yield of 38%, m.p.245-248°C.
[0121] 1 H NMR (300MHz, DMSO-d 6 ): δ10.423(s, 1H), 10.191(s, 1H), 7.639(t, 1H J=5.1Hz), 6.253(d, 1H, J=2.4Hz), 6.118(d, 1H, J=2.4Hz ),3.480(m,2H),4.448(br,4H),2.925(br,4H),2.659(s,3H);1.515(m,2H),1.261(m,2H),0.882(t,3H, J=7.2Hz); HRMS Calcd.For C 19 h 26 N 3 o 4 S(M+H + )392.1644;found.392.1632.
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