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A class of xanthochromone compounds and their preparation method and use

A technology of xanthochromone and compounds, applied in the field of pharmacy, can solve problems such as gallbladder toxicity

Active Publication Date: 2018-04-13
SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Gallbladder toxicity has been reported with existing TGR5 agonists, as well as cardiovascular toxicity

Method used

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  • A class of xanthochromone compounds and their preparation method and use
  • A class of xanthochromone compounds and their preparation method and use
  • A class of xanthochromone compounds and their preparation method and use

Examples

Experimental program
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Effect test

preparation example Construction

[0064] The preparation of embodiment 1 compound HYH1

[0065]

[0066] Step a: o-hydroxyacetophenone (compound 1, 10g, 73.5mmol, 1eq) was dissolved in N,N-dimethylformamide dimethyl acetal (DMF-DMA) 15ml, 113.9mmol, 1.55eq), The mixture was reacted at 100°C for 2 hours, and the reaction was completed. Cooling, precipitated solid, filtered, and washed with 30ml ethyl acetate to obtain intermediate product (E)-3-(dimethylamino)-1-(2-hydroxyphenyl)-propenone (compound 2), 1 H NMR (300MHz, CDCl 3 )δ9.20(s, 1H), 8.08(s, 1H), 7.51(m, 2H), 7.03(s, 1H), 4.60(s, 1H), 2.91(s, 6H).

[0067] Step b: (E)-3-(dimethylamino)-1-(2-hydroxyphenyl)-propenone (13g, 68mmol, 1eq) and elemental iodine (34.5g, 136mmol, 2eq) and pyridine (5.5ml , 68mmol, 1eq) was dissolved in 150ml chloroform and reacted for 6 hours, and the reaction was completed. Cool, add 150ml sodium sulfite saturated solution to remove excess iodine, extract three times with 150ml ethyl acetate respectively, combine organic...

Embodiment 2

[0076] The preparation of embodiment 2 compound HYH2

[0077] It was prepared in the same manner as in Example 1 except that 6-fluoro-o-hydroxyacetophenone was used instead of o-hydroxyacetophenone.

[0078]

[0079] 1 H NMR (300MHz, CDCl 3 )δ9.10(s,1H),8.57–8.44(m,2H),7.72–7.54(m,3H),7.42(d,J=3.0Hz,1H),7.36(dd,J=8.7,5.2Hz ,2H),7.30–7.20(m,4H),7.15–6.94(m,4H),3.83(s,2H).

Embodiment 3

[0080] The preparation of embodiment 3 compound HYH3

[0081] It was prepared in the same manner as in Example 1 except that 5-methoxy-o-hydroxyacetophenone was used instead of o-hydroxyacetophenone.

[0082]

[0083] 1 H NMR (300MHz, CDCl 3 )δ9.10(s,1H),8.53(d,J=10.2Hz,3H),7.73(s,1H),7.44(s,1H),7.39–7.31(m,2H),7.24(d,J =16.2Hz,7H),7.02(s,2H),3.93(s,3H),3.81(s,2H).

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Abstract

The invention provides a xanthone cross-color ketone compound having a structure represented by a general formula I (shown in the specification) or medicinal salt thereof, a preparation method of the xanthone cross-color ketone compound, a pharmaceutical composition containing the xanthone cross-color ketone compound and application of the xanthone cross-color ketone compound in preparation of medicines for treating or preventing diseases relevant with in-vivo energy imbalance, glycometabolism imbalance and / or apoptosis.

Description

technical field [0001] The invention belongs to the field of pharmacy, and in particular relates to a new type of xanonechromone compound or a pharmaceutically acceptable salt thereof, a pharmaceutical composition containing the compound, a preparation method and an application thereof. Background technique [0002] The bile acid receptor TGR5 (Takeda G-protein coupled Receptor5) is one of the hot targets reported in recent years for the treatment of diabetes. It belongs to the G protein-coupled receptor family (GPCRs) rhodopsin-like protein family. Also known as M-BAR, GPR131, BG37, etc., it is a lipid receptor expressed on the cell membrane [Maruyama, T. etal. Biochem. Biophys. Res. Commun. 2002, 298 (5), 714-719.; Kawamata, Y.etal.J.Biol.Chem.2003,278(11),9435-9440], widely distributed in the body. The expression level of TGR5 in different tissues is different, and the expression level is higher in the gallbladder, followed by the placenta, spleen, and intestine; the exp...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D405/14C07D417/14C07D413/14A61K31/506A61K31/538A61P3/04A61P3/06A61P3/10A61P1/16A61P35/00A61P13/12A61P9/12
Inventor 胡有洪冷颖陈红宁萌萌
Owner SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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