Indole derivatives
A technology of indole and compounds, applied in the field of novel indole derivatives, can solve problems such as side effects of antidiabetic agents, lactic acidosis, hypoglycemia, etc.
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Embodiment 1
[0162] 4-Chloro-3-(4-ethylphenylmethyl)-1-(β-D-glucopyranosyl)indole
[0163] (1) Under argon atmosphere, reflux overnight 4-chloroindoline (2.88 g) and D-glucose (3.38 g) in ethanol (150 ml)-H 2 O (10 mL). The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (chloroform:methanol=100:0 to 88:12) to obtain 4-chloro-1-(β-D-glucopyranosyl ) indole (3.35 g). APCI-Mass m / Z 316 / 318(M+H). 1 H-NMR (DMSO-d6) δ2.87-3.02 (m, 2H), 3.07-3.12 (m, 1H), 3.20-3.32 (m, 2H), 3.38-3.47 (m, 2H), 3.51-3.60 ( m, 2H), 3.68-3.73(m, 1H), 4.34-4.37(m, 1H), 4.63(d, J=8.3Hz, 1H), 4.93(d, J=5.1Hz, 1H), 5.03(d , J=4.0Hz, 1H), 5.06(d, J=4.5Hz, 1H), 6.53(d, J=8.0Hz, 1H), 6.60(d, J=8.0Hz, 1H), 6.99(t, J = 7.9Hz, 1H).
[0164] (2) Dissolve the above compound (3.3 g) in 1,4-dioxane (150 ml), and add 2,3-dichloro-5,6-dicyano-1,4-benzoquinone in it (2.85 grams). The mixture was stirred at room temperature for 12 hours. Saturated aqueous sodium...
Embodiment 2
[0171] 3-(4-Ethylphenylmethyl)-4-fluoro-1-(β-D-glucopyranosyl)indole
[0172] (1) Under argon atmosphere, reflux 4-fluoroindoline (185 mg) and D-glucose (267 mg) in H 2 O (0.74 mL)-ethanol (9 mL) mixture for 24 hours. The solvent was evaporated under reduced pressure to give crude 4-fluoro-1-(β-D-glucopyranosyl)indoline, which was used in the next step without further purification.
[0173] (2) The above compound was suspended in chloroform (8 mL), and pyridine (0.873 mL), acetic anhydride (1.02 mL) and 4-(dimethylamino)pyridine (catalytic amount) were successively added thereto. After stirring at room temperature for 21 hours, the reaction solvent was evaporated under reduced pressure. The residue was dissolved in ethyl acetate, and the solution was washed twice with 10% aqueous copper(II) sulfate, with saturated aqueous sodium bicarbonate, and dried over magnesium sulfate. Insoluble materials were removed by filtration, and the filtrate was evaporated under reduced pressu...
Embodiment 3
[0180] 4-Chloro-3-(4-ethoxyphenylmethyl)-1-(β-D-glucopyranosyl)indole
[0181] (1) Process the 4-chloro-1-(2,3,4,6-tetra-O-acetyl-β-D- glucopyranosyl)indole and 4-ethoxybenzoyl chloride to give 4-chloro-1-(2,3,4,6-tetra-O-acetyl-β-D- Glucopyranosyl)indol-3-yl 4-ethoxyphenyl ketone. APCI-Mass m / Z630 / 632(M+H). 1 H-NMR (DMSO-d6) δ1.37(t, J=7.0Hz, 3H), 1.69(s, 3H), 1.98(s, 6H), 2.04(s, 3H), 4.11-4.12(m, 2H ), 4.14(q, J=7.3Hz, 2H), 4.28-4.32(m, 1H), 5.29(t, J=9.7HZ, 1H), 5.54(t, J=9.5Hz, 1H), 5.71(t , J=9.2Hz, 1H), 6.32(d, J=9.0Hz, 1H), 7.04(d, J=8.8Hz, 2H), 7.25(d, J=7.5Hz, 1H), 7.35(t, J =8.0Hz, 1H), 7.79(d, 1H), 7.99(d, J=8.8Hz, 2H), 8.07(s, 1H).
[0182] (2) Process the above-mentioned 4-chloro-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)indole in a manner similar to Example 2-(5) -3-yl 4-ethoxyphenyl ketone (500 mg) to give crude 4-chloro-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl ) indol-3-yl 4-ethoxyphenylmethanol was used directly in the next step without further ...
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