Xanthone sulfonamide derivative as well as preparation method and application thereof
A technology of xanthone sulfonamide and derivatives, applied in the field of compounds, can solve the problems of difficult synthesis, high cost, low yield, etc., and achieve the effects of strong α-glucosidase inhibitory activity and good drug selection
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Embodiment 1
[0085] Embodiment 1: Compound 6-Me and its synthesis
[0086] Mix excess p-toluenesulfonyl chloride (1.25g, 6.58mmol, 16 equivalents) with 0.100g (0.41mmol) of 6-amino-1,3-dihydroxy-9H-xanthene-9-one in anhydrous Add 10 mL of dry redistilled pyridine under anaerobic conditions, and react at room temperature for 12 hours. Pour the reaction mixture into hydrochloric acid, dissolve the solid in 20 mL of methanol after suction filtration, add 3 mL of 1M sodium hydroxide solution to reflux for 2 hours, remove most of the solvent, pour the system into saturated sodium chloride solution, suction filter, dry, column chromatography. 94 mg of the product was obtained with a yield of 58%.
[0087] 1 H NMR spectrum (solvent DMSO-d 6 , TMS internal standard, ppm) δ12.83(s, 1H), 11.22(s, 1H), 11.09(s, 1H), 7.98(d, J=8.5Hz, 1H), 7.79(d, J=7.8Hz , 2H), 7.40 (d, J = 7.9Hz, 2H), 7.18 (d, J = 8.7Hz, 2H), 6.38 (s, 1H), 6.19 (s, 1H), 2.34 (s, 3H).
Embodiment 2
[0088] Embodiment 2: Compound 6-H and its synthesis
[0089] Mix excess benzenesulfonyl chloride (1.26mL, 10.0mmol, 24.4eq) with 0.100g (0.41mmol) of 6-amino-1,3-dihydroxy-9H-xanthene-9-one, the reaction conditions and synthesis method are the same as Embodiment 1, obtain product 135mg, productive rate 86.5%.
[0090] 1 H NMR spectrum (solvent DMSO-d 6 , TMS internal standard, ppm) δ12.81(s, 1H), 11.31(s, 1H), 11.05(s, 1H), 7.99(d, J=8.5Hz, 1H), 7.91(d, J=7.6Hz , 2H), 7.63 (m, 3H), 7.20 (s, 1H), 6.18 (d, J=2.2Hz, 1H).
Embodiment 3
[0091] Embodiment 3: Compound 6-OMe and its synthesis
[0092] Mix excess p-methoxybenzenesulfonyl chloride (1.1g, 5.36mmol, 13 equivalents) with 0.100g (0.41mmol) of 6-amino-1,3-dihydroxy-9H-xanthene-9-one, the reaction conditions 1. The synthetic method is the same as in Example 1, and 84 mg of the product is obtained, with a yield of 49.6%.
[0093] 1 H NMR spectrum (solvent DMSO-d 6 , TMS internal standard, ppm) 1 H NMR (400MHz, DMSO-d 6 )δ12.83(s,1H),11.18(s,1H),11.05(s,1H),7.98(d,J=8.5Hz,1H),7.84(d,J=9.0Hz,2H),7.17( s, 2H), 7.11 (d, J=9.0Hz, 2H), 6.37 (d, J=2.1Hz, 1H), 6.18 (d, J=2.1Hz, 1H), 3.80 (s, 3H).
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