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Stilbene coumarin derivative as well as preparation method and application thereof

A technology of stilbene and coumarin, which is applied in the field of novel stilbene coumarin derivatives and preparation, can solve the problems of poor selectivity, single structure, low bioavailability, etc., and achieves compound structure optimization and reaction The effect of high yield and simple process

Active Publication Date: 2015-09-09
黄山市开发投资集团有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to its poor selectivity, single structure and low bioavailability, the current research focus is on the development of its derivatives, in order to screen out stilbene derivatives with high efficiency, low toxicity and good selectivity.

Method used

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  • Stilbene coumarin derivative as well as preparation method and application thereof
  • Stilbene coumarin derivative as well as preparation method and application thereof
  • Stilbene coumarin derivative as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Example 1: 3-((E)-3-(2,4-dimethoxy-6-(4-methoxystyryl)phenyl)acryloyl)-2H-pyran-2-one (Compound 1) Preparation

[0031]

[0032] (1) Take a 100mL round-bottomed flask, add N,N-dimethylformamide (30mL) in an ice-water bath, and weigh resveratrol trimethyl ether (13.5g, 0.075mol), add 10mL N,N- Dimethylformamide was dissolved, and then added to a round bottom flask, and phosphorus oxychloride (7 mL, 0.075 mol) was slowly added dropwise. After the dropwise addition, the solution was returned to room temperature for reaction, and stirred for 1 h. After the reaction, take a 1000mL beaker, add 500mL ice water and 100mL ethyl acetate, then add the reaction solution dropwise, add solid sodium carbonate in portions under stirring until no bubbles are generated, and precipitate a light yellow solid overnight, filter and dry , column chromatography to obtain (E)-2,4-dimethoxy-6-(4-methoxystyrene)benzaldehyde (compound A). The product was a yellow solid with a yield of 92.7% a...

Embodiment 2

[0035] Example 2: 3-((E)-3-(2,4-dimethoxy-6-(4-methoxystyryl)phenyl)acryloyl)-8-methoxy-2H-benzene Preparation of pyran-2-one (compound 2)

[0036]

[0037] The preparation method is the same as in Example 1. The difference is that 3-methoxy salicylaldehyde is used instead of salicylaldehyde to obtain the target compound as a yellow-brown solid powder with a yield of 63% and a melting point of 115-116°C. 1 H NMR (600MHz, CDCl 3 )δ8.44(s,1H),8.23(d,J=15.7Hz,1H),7.92(d,J=15.7Hz,1H),7.49(d,J=8.7Hz,2H),7.38(d, J=16.0Hz, 1H), 7.22(d, J=7.9Hz, 1H), 7.18(dd, J=7.8, 1.3Hz, 1H), 7.13(dd, J=8.0, 1.2Hz, 1H), 6.91( dd,J=17.3,12.4Hz,3H),6.71(d,J=2.3Hz,1H),6.41(d,J=2.3Hz,1H),3.96(s,3H),3.91(s,3H), 3.88(s,3H),3.83(s,3H). 13 C NMR (151MHz, cdcl 3 )δ190.23(s),164.60(s),164.03(s),162.26(s),161.19(s),149.77(s),149.68(s),147.46(s),145.20(s),141.81( s), 135.04(s), 132.52(s), 130.89(s), 129.21(s), 129.07(s), 127.55(s), 127.19(s), 123.61(s), 121.91(s), 118.43( s),117.99(s),116.81(s),106.3...

Embodiment 3

[0038] Example 3: 3-((E)-3-(2,4-dimethoxy-6-(4-methoxystyryl)phenyl)acryloyl)-7-methoxy-2H-benzene Preparation of pyran-2-one (compound 3)

[0039]

[0040] The preparation method was the same as in Example 1, except that 4-methoxy salicylaldehyde was used instead of salicylaldehyde to obtain the target compound as a yellow solid powder with a yield of 69% and a melting point of 137-139°C. 1 H NMR (600MHz, DMSO) δ8.59(s,1H),8.19(s,1H),8.02–7.95(m,2H),7.82(d,J=8.7Hz,1H),7.68–7.61(m, 2H), 7.53(d, J=8.7Hz, 2H), 7.33(d, J=16.1Hz, 1H), 7.22(d, J=8.7Hz, 1H), 7.08(d, J=16.1Hz, 1H) ,6.90(d,J=8.7Hz,2H),3.88–3.84(m,9H),3.75(s,3H). 13 C NMR (151MHz, DMSO) δ190.16(s), 164.61(s), 164.02(s), 162.26(s), 161.96(s), 158.88(s), 152.32(s), 149.44(s), 145.20 (s), 141.83(s), 135.02(s), 132.49(s), 131.35(s), 129.19(s), 129.10(s), 127.59(s), 124.77(s), 121.57(s), 120.34 (s),117.23(s),116.79(s),113.47(s),106.40(s),100.21(s),59.63(s),59.35(s),59.07(s),58.25(s).MS (EI):469.17(C 30 h 26 o 7 ,...

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Abstract

The invention discloses a stilbene coumarin derivative as well as a preparation method and an application thereof, and relates to the technical field of medicine synthesis. The structure general formula of the stilbene coumarin derivative is shown in formula (1) which is specified in the description. The synthesis process disclosed by the invention has the characteristics of being simple and practicable in reaction, and high in product yield; moreover, the synthesised stilbene coumarin derivative is good in inhibitory activity and selectivity on anthropogenic monoamine oxidases (hMAO-A and hMAO-B), and therefore can be used for preparing a monoamine oxidase inhibitor.

Description

technical field [0001] The invention relates to the technical field of drug synthesis, in particular to a class of novel stilbene coumarin derivatives, a preparation method and application. Background technique [0002] Coumarin is a class of compounds with benzoα-pyrone structure, which has a wide distribution and use in different species of plants, especially in Umbelliferae, Rutaceae, Compositae, Fabaceae, In plants such as Solanaceae, it also exists in animals and microorganisms, such as leucomycins of luminescent fungi, isocoumarins isolated from marine fungi, etc. Coumarin compounds have very important pharmacological effects, such as anti-tumor, anti-HIV, anti-oxidation, anti-arrhythmia, anti-inflammatory, analgesic and antibacterial. [0003] The antitumor activity of coumarin has aroused widespread attention at home and abroad. Warfarin sodium is the earliest coumarin used in anticancer research (The Johns Hopkins Medical Journal, 1968, 123(6):305), and it has obv...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/12A61K31/366
CPCC07D311/12
Inventor 阮班锋程慧洁李红林杨亿弟李青山
Owner 黄山市开发投资集团有限公司
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