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7,8-dehydrogenated vitis amurensis vine pentosidine derivatives as well as preparation method and pharmaceutical composition thereof and application of derivatives and pharmaceutical composition

A technology of glupapentin and its derivatives, which is applied in the field of biomedicine and can solve problems such as structure-activity relationship optimization of compound systems that have not been reported in the literature.

Active Publication Date: 2019-05-07
INST OF MATERIA MEDICA AN INST OF THE CHINESE ACAD OF MEDICAL SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The research on the activity of the Amurensin H compound itself has been publicly reported by our research group, but the structure-activity relationship research on the structure optimization and anti-inflammatory activity of the compound system has not been reported in the literature so far

Method used

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  • 7,8-dehydrogenated vitis amurensis vine pentosidine derivatives as well as preparation method and pharmaceutical composition thereof and application of derivatives and pharmaceutical composition
  • 7,8-dehydrogenated vitis amurensis vine pentosidine derivatives as well as preparation method and pharmaceutical composition thereof and application of derivatives and pharmaceutical composition
  • 7,8-dehydrogenated vitis amurensis vine pentosidine derivatives as well as preparation method and pharmaceutical composition thereof and application of derivatives and pharmaceutical composition

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specific Embodiment approach

[0135] In order to further clarify the present invention, a series of examples are given below, these examples are completely illustrative, they are only used to specifically describe the present invention, and should not be construed as limiting the present invention. The synthetic route of intermediate 1d in the embodiment:

[0136]

[0137] The synthetic route of compound 1~9 in the embodiment:

[0138]

[0139] Synthetic end product (compound code number is corresponding to the compound code number in the embodiment)

[0140]

[0141]

[0142]

[0143] The synthetic method of compound 1~9 in the embodiment:

[0144] Method A: Compound 1d (100 mg, 0.23 mmol) was dissolved in 50 mL of dry dichloromethane, and HOBt (37.6 mg, 0.28 mmol) and EDCI (53.0 mg, 0.28 mmol) were added in sequence. After fully stirring for 20 min, alcohol or phenolic compound (1.2 equiv) was added, stirred at room temperature for 4 h, the disappearance of raw materials was monitored by...

Embodiment 1

[0147] Octyl 2-(4-methoxyphenyl)-3-(3,5-dimethoxyphenyl)-6-methoxy-4-benzofurancarboxylate (1)

[0148] Synthesized according to method A, the alcohol compound added was n-octanol (1.2 equiv), petroleum ether: acetone (2:1) was used as the developing solvent, and silica gel preparation plate was prepared and separated to obtain the target product with a yield of 32.9%. The physical and chemical parameters of compound 1 are as follows:

[0149] Compound 1: Pale yellowish brown solid, yield=32.9%. 1 H NMR (400MHz, acetone-d 6 ): δ 7.50 (d, J = 8.8Hz, 2H), 7.37 (d, J = 2.4Hz, 1H), 7.14 (d, J = 2.4Hz, 1H), 6.91 (d, J = 8.8Hz, 2H) ,6.55(t,J=2.4Hz,1H),6.50(d,J=2.4Hz,2H),3.94(s,3H),3.81(s,3H), 3.79(s,6H),3.62(t, J=6.8Hz, 2H), 1.43–1.11(m, 12H), 0.86(t, J=6.8Hz, 3H); 13 C NMR (125MHz, acetone-d 6 ):δ167.73,162.22(2×C),160.90,158.36,156.13,152.22, 136.96,129.08(2×C),127.51,123.66,121.64,116.87,114.75(2×C),113.23,108.53 (2 ),100.51,99.30,65.65,56.43,55.73(2×C),55.64,32.53,29.96,29...

Embodiment 2

[0151] 2-(4-methoxyphenyl)-3-(3,5-dimethoxyphenyl)-6-methoxy-4-benzofurancarboxylic acid-2-furylmethyl ester (2)

[0152] Synthesized according to method A, the alcohol compound added was 2-furan methanol, petroleum ether: ethyl acetate: dichloromethane (5:1:2) was used as the developing solvent, and the silica gel preparation plate was prepared and separated to obtain the target product with a yield of 47.1 %. The physicochemical parameters of compound 2 are as follows:

[0153] Compound 2: off-white solid, yield=54.4%. 1 H NMR (500MHz, acetone-d 6 ): δ7.51(d, J=9.0Hz, 2H), 7.48(dd, J=2.0, 1.0Hz, 1H), 7.37(d, J=2.0Hz, 1H), 7.15(d, J=2.0 Hz ,1H),6.91(d,J=9.0Hz,2H),6.59(t,J=2.0Hz,1H),6.51(d,J=2.0Hz,2H), 6.36(dd,J=3.0,2.0Hz ,1H),6.31(d,J=3.0Hz,1H),4.58(s,2H),3.93(s,3H),3.81(s,3H),3.80(s,6H); 13 C NMR (125MHz, acetone-d 6 ):δ167.09,162.28(2×C),160.94, 158.36,156.11,152.34,150.28,144.15,136.98,129.02(2×C),126.55,123.61,121.96, 116.82,114.7113.29(2×C), ,111.36,108.48(2×C),10...

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Abstract

The invention discloses novel 7,8-dehydrogenated vitis amurensis vine pentosidine (amurensin H) derivatives with anti-inflammatory activity and anti-inflammatory activity thereof. Specifically, the invention relates to the novel 2,3-diaryl-4-substituted benzofuran derivatives with a novel structure represented by a general formula (I) shown in the description or a medically-acceptable salt of thederivatives. The invention discloses an application of the derivative monomers or the pharmaceutical composition of the derivatives in clinical treatment of inflammatory related diseases.

Description

technical field [0001] The present invention relates to the field of biomedicine, in particular to a class of 7,8-dehydrogluphine (Amurensin H) derivatives with a benzofuran structure or a medically acceptable salt thereof, and a pharmaceutical combination containing these derivatives Drugs and their application in the clinical treatment of inflammatory related diseases. Background technique [0002] Inflammation is the basis of human diseases, and it is a key link in the pathological process of diseases. However, the current anti-inflammatory drugs, such as corticosteroids and non-steroidal anti-inflammatory drugs, still have many problems in clinical application, such as easy to cause gastrointestinal discomfort, bleeding, increase the occurrence of heart disease or systemic coagulation disorders, etc. Risk of Adverse Reactions. Therefore, finding safer and more effective anti-inflammatory drugs is still an important task in the current research and development of anti-i...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/80C07D405/12A61K31/404A61K31/343A61K31/4192A61P29/00A61P37/06A61P19/02A61P19/08A61P17/06A61P17/00A61P1/00A61P31/00A61P11/00A61P11/06A61P13/00A61P1/16A61P5/14A61P13/12A61P9/10A61P19/06A61P17/02
Inventor 姚春所林明宝侯琦白金叶石建功张纪法杨慧滕彬豪
Owner INST OF MATERIA MEDICA AN INST OF THE CHINESE ACAD OF MEDICAL SCI
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