Xanthone bridged sulfonamide derivatives, preparation method and application thereof
A technology for bridging sulfonamide and derivatives with xanthone, applied in the field of medicine, can solve the problems of low α-glucosidase inhibitory activity, many impurities and high cost, and achieve excellent α-glucosidase inhibitory activity and synthetic route Clear, low-cost production results
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[0017] The present invention also provides a preparation method of xanthone-bridged sulfonamide derivatives, comprising:
[0018] reacting the compound of formula (II) with the compound of formula (III) to obtain the compound of formula (I);
[0019]
[0020] Wherein, R is hydrogen, cyano, nitro, halogen, C1-C10 alkyl, C1-C10 alkoxy, C2-C10 amido or halogen-substituted C1-C6 alkyl;
[0021] The n is an integer of 0-12.
[0022] According to the present invention, the present invention reacts the compound of the formula (II) structure with the compound of the formula (III) structure to obtain the compound of the formula (I) structure; wherein, the compound of the formula (II) structure and the formula (III) structure The molar ratio of the compound is preferably 1: (1~1.1), more preferably 1: 1; The reaction auxiliary agent of described reaction is preferably triethylamine; The solvent of described reaction is preferably dichloromethane, chloroform or 1, 2-dichloroethane; ...
Embodiment 1
[0051] The synthetic method of compound VI
[0052] In a 100mL double necked round bottom flask, add 5mmol of compound V, 25mmol of K 2 CO 3 , 100mmol of Br(CH 2 ) n Br, 40mL of acetone, reacted at 65°C until the conversion of the raw materials was complete. The reaction liquid was filtered, the filter residue was washed with 100 mL of methanol, the combined filtrate was collected, the filtrate was concentrated, and the compound VI was obtained by column chromatography with a yield of 44.8-90.6%.
[0053] The synthetic method of compound IV
[0054] In a 100mL double necked round bottom flask, add 5mmol of compound VI, 25mmol of phthalimide (Phthalimide), 25mmol of Cs 2 CO 3 , 40mL of acetone, reacted at 65°C until the raw materials were completely reacted. The reaction solution was filtered, the filter residue was washed with 100 mL of methanol, the combined filtrate was collected, the filtrate was concentrated, and the compound IV was obtained by column chromatography...
Embodiment 2
[0058] Synthesis of Compounds I-a~I-n
[0059] Compound I-a and its synthesis
[0060] In a 25mL double-neck round bottom flask, add 0.8mmol of compound II (n is 3), 0.8mmol of 4-methylbenzenesulfonyl chloride, 4.0mmol of Et 3 N, 5mL CH 2 Cl 2 , react at room temperature until the raw materials are completely reacted. The reaction solution was concentrated, dried, and subjected to column chromatography to obtain 247 mg of the product with a yield of 66.3%.
[0061] Compound I-a provided by the invention, light yellow solid, molecular formula C 25 h 25 NO 6 S, molecular weight 467.14026.
[0062] Chinese name: N-(5-((1-hydroxy-9-oxo-9H-xanthene-3-yl)oxy)pentyl)-4-methylbenzenesulfonamide,
[0063] English name:
[0064] N-(5-((1-hydroxy-9-oxo-9H-xanthen-3-yl)oxy)pentyl)-4-methylbenzenesulfonamide;
[0065] 1 H NMR (400MHz, DMSO-d 6 )δ12.78(s, 1H), 8.13(dd, J=8.0, 1.7Hz, 1H), 7.87(ddd, J=8.7, 7.1, 1.7Hz, 1H), 7.73-7.66(m, 2H), 7.59 (dd, J=8.7, 0.9Hz, 1H), 7.56-7.45(...
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