Silybin esters derivatives and preparation and use thereof
A technology of silibinin and derivatives, which is applied in the field of preparation of silibinin ester derivatives, and can solve the problems of limited drug market, insufficient water solubility and bioavailability, etc.
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Embodiment 1
[0039] Example 1: Compound I-1, p-methoxybenzoic acid [3-(hydroxyl-3-methoxyphenyl)-6-(2,3-dihydro-3,5,7-trihydroxyl-4 Preparation of -oxo-benzopyran-2-)-2,3-dihydro-1,4-benzodioxane-2-]-methyl ester:
[0040]
[0041] Add 1 gram of compound I-a (silibinin), 0.6 gram of p-methoxybenzoic acid and 1.6 gram of triphenylphosphine into a dry reaction flask, dissolve with 20 milliliters of anhydrous tetrahydrofuran, add 1 gram of azodicarboxylate Ethyl ester was stirred at room temperature for 10 hours after the addition, the solvent was distilled off under reduced pressure, 5 ml of chloroform was added, the white solid was removed by filtration, and the mother liquor was subjected to column chromatography to obtain 0.7 g of a light yellow powder with a yield of 47%.
[0042] Compound I-1: Rf (chloroform:methanol=50:1)=0.33; 1 H NMR (400MHz, deuterated chloroform) δ: 3.80(s, 3H, OCH 3 ), 3.86(s, 3H, OCH 3 ), 4.20(m, 1H, H-9′a), 4.34(m, 1H, H-8′), 4.48(m, 1H, H-9′b), 4.53(m, 1H...
Embodiment 15
[0062] Example 15: Compound I-15 (p-methoxybenzoic acid [3-hydroxy-3-methoxyphenyl)-8-methoxy-6-(2,3-dihydro-3,5,7 - Preparation of trihydroxy-4-oxo-benzopyran-2-)-2,3-dihydro-1,4-benzodioxane-2-]-methyl ester):
[0063] According to the method of Example 1, with 2-[2,3-dihydro-3-(4-hydroxy-3-methoxyphenyl)-2-hydroxymethyl-8-methoxy-1,4- Benzodioxane-6-]-2,3-dihydro-3,5,7-trihydroxy-4H-1-benzopyran-4-one instead of silybin can give compound I-15 : Rf (chloroform: methanol = 50: 1) = 0.28; 1 H NMR (400MHz, deuterated chloroform) δ: 3.80 (s, 3H, OCH3), 3.84 (s, 3H, OCH3), 3.86 (s, 3H, OCH3), 4.22 (m, 1H, H-9'a) , 4.33.(m, 1H, H-8'), 4.50(m, 1H, H-9'b), 4.51(m, 1H, H-3), 4.98(d, J=12.0Hz, 1H, H -2), 5.02(d, J=8.0Hz, 1H, H-7'), 6.00(s, 1H, H-6), 6.03(s, 1H, H-8), 6.95(d, J=8.8 Hz, 1H, H-3, 5), 6.86-7.15(m, 5H, Ar-H), 7.95(d, J=8.8Hz, 1H, H-2, 6) 11.24(s, 1H , 5-OH); ESI-MS: 645[M-1] + .
Embodiment 16
[0064] Example 16: p-nitrobenzoic acid [3-(4-hydroxy-3-methoxyphenyl)-8-methoxy-6-(2,3-dihydro-3,5,7-trihydroxy - Preparation of 4-oxo-benzopyran-2-)-2,3-dihydro-1,4-benzodioxane-2-]-methyl ester:
[0065] According to the same method as in Example 15, compound I-16 can be obtained: Rf (chloroform: ethyl acetate: formic acid = 50: 1: 0.25) = 0.15; 1 H NMR (400MHz, deuterated chloroform) δ: 3.87 (s, 3H, OCH3), 3.88 (s, 3H, OCH3), 4.35 (m, 1H, H-9'a), 4.50 (m, 1H, H- 8'), 4.57(m, 2H, H-3, H-9'b), 4.96(d, J=6.8Hz, 1H, H-7'), 5.01(d, J=12.0Hz, 1H, H -2), 6.01(s, 1H, H-6), 6.13(s, 1H, H-8), 7.59(d, J=8.8Hz, 2H, 2, 6), 6.93-8.16(m, 5H, Ar-H), 8.33(d, J=8.8Hz, 2H, 3, 5), 11.20(s, 1H, 5-OH); ESI-MS: 660[M-1]+ .
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