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Xanthone sulfonamide derivatives, preparation method and application thereof

A technology of xanthone sulfonamide and derivatives, applied in the field of compounds, can solve the problems of high cost, difficult synthesis, low yield, etc., and achieve the effect of good drug selection and strong α-glucosidase inhibitory activity

Active Publication Date: 2019-11-15
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Their synthesis is difficult, the yield is low, and the cost is high

Method used

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  • Xanthone sulfonamide derivatives, preparation method and application thereof
  • Xanthone sulfonamide derivatives, preparation method and application thereof
  • Xanthone sulfonamide derivatives, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

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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Abstract

The invention relates to the technical field of compounds and in particular relates to a xanthone sulfonamide derivative as well as a preparation method and application thereof. The xanthone sulfonamide derivative provided by the invention has a general structural formula shown as formula I, wherein R is selected from alkyl, H-, MeO-, a halogen substituent group, AcNH-, HO- or H2N-. According to the xanthone sulfonamide derivative, a sulfuryl chloride compound and amino xanthone are used as reaction raw materials, and a series of xanthone sulfonamide derivatives with same active units are prepared through simple and convenient sulfonylation reaction and substitution reaction; the xanthone sulfonamide derivatives have relatively high alpha-glucosidase inhibition activity and can be applied to preparation of drugs for lowering blood glucose, so that more and better drug selection can be provided for patients with diabetes mellitus.

Description

technical field [0001] The present invention relates to the technical field of compounds, and more specifically relates to xanthone sulfonamide derivatives and their preparation methods and applications. Background technique [0002] Type Ⅱ diabetes is also known as non-insulin-dependent diabetes, and more than 90% of diabetic patients belong to this type. α-glucosidase inhibitors are a class of drugs for the treatment of type 2 diabetes. The currently marketed drugs include acarbose, miglitol and voglibose, all of which are sugar compounds or sugar derivatives. Its side effects are minor, and adverse reactions mainly include flatulence and diarrhea. [0003] It has been proved in the literature that acarbose, voglibose and miglitol have lower inhibitory activity on α-glucosidase, which leads to a larger dosage and a higher possibility of side effects. high. Currently marketed α-glucosidase drugs include acarbose, miglitol and voglibose, all of which are sugar compounds o...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D311/86A61P3/10
CPCC07D311/86
Inventor 汪波段文迪曹警予杨至蓉崔金凤陈悠南王璟
Owner SUN YAT SEN UNIV
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