Applications of Amurensin H derivatives in preparation of drugs for treating liver related diseases

A technology of glupapentin and its derivatives, which is applied in the field of biomedicine and can solve the problems of few research reports

Inactive Publication Date: 2019-11-12
INST OF MATERIA MEDICA CHINESE ACAD OF MEDICAL SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in addition to the isolation and identification of natural products, the systematic structural modification and structure-activity relationship research of active oligomer compounds (especially dimers) is still a new research field. There are few research reports

Method used

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  • Applications of Amurensin H derivatives in preparation of drugs for treating liver related diseases
  • Applications of Amurensin H derivatives in preparation of drugs for treating liver related diseases
  • Applications of Amurensin H derivatives in preparation of drugs for treating liver related diseases

Examples

Experimental program
Comparison scheme
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specific Embodiment approach

[0115] In order to further illustrate the present invention, a series of examples are given below (the compound code number is corresponding to the compound code number in the examples), these examples are completely illustrative, and they are only used to specifically describe the present invention, and should not be interpreted as Invention Limitations.

[0116] The synthetic route of intermediate compound 1c in the embodiment:

[0117]

[0118] The synthetic route of intermediate compound 2b, 3b, 2c and 3c in the embodiment:

[0119]

Embodiment 1

[0121] 5-[6-Acetoxy-2-[4-acetoxyphenyl]-4-[2-(4-acetoxyphenyl)ethyl]-3-benzofuranyl]-1,3 -Diphenol-1,3-diacetate (1)

[0122] The synthetic route of compound 1:

[0123]

[0124] 100 mg of compound 1c was dissolved in 6 ml of ethyl acetate, 7.11 mg of Pd / C (10%) was added, reacted under pressure for 1 h under a hydrogen atmosphere, filtered to remove Pd / C, and the filtrate was concentrated under reduced pressure to obtain 93.8 mg (0.140 mmol) of white solid compound 1 ), yield 93.5%, m.p.79-81°C.

[0125] Compound 1: UVλ max (MeOH,logε):307.4(4.43)nm; 1 H NMR (CD 3 COCD 3 ,500MHz)δ:7.55(2H,d,J=8.5Hz,H-2a,6a),7.31(1H,d,J=1.5Hz,H-14b),7.26(2H,d,J=2.0Hz, H-10a, 14a), 7.12 (1H, t, J = 2.0Hz, H-12a), 7.09 (2H, d, J = 8.5Hz, H-3a, 5a), 6.89 (1H, J = 1.5Hz, H-12b),6.87-6.88(4H,m,H-2b,6b,3b,5b),2.79-2.83(2H,m,H 2 -7b),2.61-2.65(2H,m,H 2-8b),2.29(3H,s,OCOCH 3 ),2.24(6H,s,OCOCH 3 ),2.21(3H,s,OCOCH 3 ); 13 C NMR (CD 3 COCD 3 ,125MHz) δ: 169.8 (O C OCH 3 ), 169.6 (O C...

Embodiment 2

[0127] 5-[6-Hydroxy-2-(4-hydroxyphenyl)-4-[2-(4-hydroxyphenyl)ethyl]-3-benzofuryl]-1,3-benzenediol (2 )

[0128] The synthetic route of compound 2:

[0129]

[0130] 100mg of compound 1 (0.154mmol) was dissolved in 3ml of dichloromethane, diluted with 3ml of methanol, and then added with 1855mg of NH 4 OAc (24.096 mmol), stirred at room temperature for 4d. After the reaction was complete, water and ethyl acetate were added for extraction, and the organic phases were combined and concentrated to dryness under reduced pressure to obtain 62 mg (0.137 mmol) of compound 2 as a yellow solid with a yield of 90.4%, m.p.240-242°C.

[0131] Compound 2: UVλ max (MeOH,logε):284.6(4.34),319.2(4.54)nm; 1 H NMR (CD 3 COCD 3 ,500MHz)δ:8.18-8.62(br s,H-OH),7.41(2H,d,J=8.5Hz,H-2a,6a),6.85 7.31(1H,d,J=2.0Hz,H-14b ),6.78(2H,d,J=8.5Hz,H-2b,6b),6.77(2H,d,J=8.5Hz,H-3a,5a),6.64(2H,d,J=8.5Hz,H -3b,5b),6.62(1H,J=2.0Hz,H-12b),6.51(1H,t,J=1.5Hz,H-12a),6.49(2H,d,J=1.5Hz,H-10a ,14a),2.68-2.71(2...

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Abstract

The invention discloses applications of Amurensin H derivatives shown as a formula (I), (II) and (III) and pharmaceutically acceptable salt thereof in the preparation of drugs for treating and/or preventing liver related diseases, and also discloses the preparation method of a compound, and applications of the pharmaceutical composition of the compound in the preparation of the drugs for treatingand/or preventing the liver related diseases.

Description

technical field [0001] The present invention relates to the field of biomedicine, in particular to a class of glupapentin derivatives or their medically acceptable salts, and the application of pharmaceutical compositions containing these derivatives in the preparation of drugs for treating and / or preventing liver-related diseases . Background technique [0002] The development of new drugs based on active natural products is one of the important ways of modern drug development. Natural products have the characteristics of wide sources, low toxicity and few side effects. Discovering natural lead compounds with significant activity from traditional Chinese herbal medicines, through structural modification, combined with systematic in vivo and in vitro activity tests and comprehensive evaluation of druggability, to find safe and efficient candidate compounds as clinically useful prototype drugs, is the key to drug research and development. important direction. Oligomeric st...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/343A61P1/16A61P31/14A61P31/20A61P37/06C07D307/80
CPCA61K31/343A61P1/16A61P31/14A61P31/20A61P37/06C07D307/80Y02A50/30
Inventor 姚春所孙华王先分刘威李梅滕彬豪张凡商昌辉
Owner INST OF MATERIA MEDICA CHINESE ACAD OF MEDICAL SCI
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