Cyano-containing resveratrol analogue and preparation method and purpose thereof

A technology for resveratrol and analogs, applied in the field of cyano-containing resveratrol analogs and their preparation, can solve the problems of inconvenient operation, limited application, environmental pollution and the like, and achieves reduction of health damage and application scope. Wide and environmentally friendly effect

Inactive Publication Date: 2016-04-20
YANBIAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0013] This preparation method uses highly toxic substances such as sodium cyanide (NaCN) or potassium cyanide (KCN) to carry out nitrilation reaction when introducing cyano groups on the ethylene unit of resveratrol. Although its reaction effect is better, the reaction needs to be carried out. 2 hours or more, the time of exposure to cyanide is longer, which causes inconvenience in the operation during the experiment...

Method used

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  • Cyano-containing resveratrol analogue and preparation method and purpose thereof
  • Cyano-containing resveratrol analogue and preparation method and purpose thereof
  • Cyano-containing resveratrol analogue and preparation method and purpose thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0041] Example 1: Preparation of Z-2-(3,5-dimethoxyphenyl)-3-(4-fluorophenyl)acrylonitrile

[0042] Synthesis of intermediate product 3,5-dimethoxybenzoic acid methyl ester 2

[0043] 14.231g (0.092mol) of 3,5-dihydroxybenzoic acid 1, 26.021g (0.189mol) of potassium carbonate and 100mL of acetone in a 500mL two-necked flask, use a constant pressure dropping funnel to slowly and uniformly add 17mL of dimethyl sulfate; about After 30 minutes of dropping, start heating and reflux for 4 hours; use thin layer chromatography to track and detect, and cool to room temperature after the reaction; filter, wash the filter residue with acetone and combine the filtrate, dry with anhydrous sodium sulfate, evaporate the solvent under reduced pressure, and dry to obtain compound 2; The yield was 90.7%, and the melting point was 41~43℃. 1 HNMR(300MHz, CDCl 3 ): δ7.18 (d, J = 2.3 Hz, 2H), 6.64 (t, J = 2.3 Hz, 1H), 3.90 (s, 3H), 3.82 (s, 6H).

[0044] Synthesis of the intermediate product 3,5-dimethox...

Embodiment 2

[0053] Example 2: Preparation of Z-2-(3,5-dimethoxyphenyl)-3-(4-chlorophenyl)acrylonitrile 6b, the reaction equation is as follows:

[0054]

[0055] Using the method similar to the synthesis of the intermediate product in Example 1, take 0.01mol of 3,5-dimethoxybenzeneacetonitrile (5), 0.01mol of 4-chlorobenzaldehyde and 20mL of methanol into a 50mL three-necked flask, stir and warm up to 60℃, add methanol Sodium 0.005mol, constant temperature reaction 4-6h, TLC tracking detection, after the reaction is completed, cool to room temperature, filter, wash with water, dry, recrystallize with methanol to obtain a white solid, the yield is 73.9%, the melting point is 114-116℃ . 1 HNMR(300MHz, CDCl 3 ): δ7.82(d,J=8.6Hz,2H), 7.46(d,J=4.6Hz,2H), 7.42(s,1H), 6.79(d,J=2.1Hz,2H), 6.49(dd , J=6.0, 3.9 Hz, 1H), 3.85 (s, 6H).

Embodiment 3

[0056] Example 3: Preparation of Z-2-(3,5-dimethoxyphenyl)-3-(4-bromophenyl)acrylonitrile 6c, the reaction equation is as follows:

[0057]

[0058] Using the method similar to the synthesis of intermediate products in Example 1, take 0.01mol 3,5-dimethoxybenzeneacetonitrile (5), 0.01mol 4-bromobenzaldehyde and 20mL methanol into a 50mL three-necked flask, stir and raise the temperature to 60℃, add methanol Sodium 0.005mol, constant temperature reaction 4-6h, TLC tracking detection, after the reaction is completed, cool to room temperature, filter, wash with water, dry, recrystallize with methanol to obtain a pale yellow solid, the yield is 66.3%, the melting point is 150-152 ℃. 1 HNMR(300MHz, CDCl 3 )δ7.91(d,J=5.4Hz,2H),7.48(s,1H),7.16(t,J=8.6Hz,2H), 6.79(d,J=2.2Hz,2H), 6.50(t, J = 2.2 Hz, 1H), 3.85 (s, 6H). 13CNMR (75MHz, CDCl3): δ 161.27, 141.08, 136.14, 132.45, 132.23, 130.71, 124.95, 117.72, 112.33, 104.32, 101.43, 55.57. IR(KBr)cm -1 : 2835(-OCH3), 2220(-CN), 858(-C=C-H)....

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Abstract

The invention provides a cyano-containing resveratrol analogue and a preparation method and application thereof, and relates to the field of medical compounds. A structure of the cyano-containing resveratrol analogue is shown in the formula of the description; 3,5-dihydroxy-benzoic acid is mainly used as a raw material, and the cyano-containing resveratrol analogue is prepared by the following steps of methylation, reduction, brominating, Abozove rearrangement, Wittig-Hornor reaction and Knoevenegal reaction; in the preparation process of the cyano-containing resveratrol analogue, the chemical substances with lower toxicity, such as trimethylsilyl cyanide and tetrabutylammonium fluoride, are used for replacing chemicals with higher toxicity, such as sodium cyanide or potassium cyanide, to introduce cyano, so that the damage to the health of an operator is greatly decreased, and the serious harm to environments is avoided. The preparation method has the advantages that the yield is higher, the environment-friendly effect is good, and multiple types of cyano-containing resveratrol analogue with anti-cancer activity on cells can be obtained.

Description

Technical field [0001] The present invention relates to the field of medicinal compounds, in particular to cyano-containing resveratrol analogues and preparation methods and uses thereof. Background technique [0002] Resveratrol is a kind of natural polyphenols with strong biological properties mainly derived from grapes (red wine), knotweed, peanuts, mulberries and other plants, also known as stilbene. It is a chemopreventive agent for tumors, as well as a chemopreventive agent for reducing platelet aggregation, preventing and treating atherosclerosis and cardiovascular and cerebrovascular diseases. The chemical name of resveratrol is (E)-3,5,4-trihydroxystilbene, and its chemical structure is shown in structural formula 1: [0003] [0004] Resveratrol [0005] Structural formula 1 [0006] In 1993, Jayafilake and other studies showed that resveratrol has anti-cancer activity because they can inhibit the activity of protein-tyrosine kinases. Resveratrol has anti-cancer activity ...

Claims

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Application Information

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IPC IPC(8): C07C253/30C07C255/37C07C255/43C07D333/24C07D307/54C07D213/57A61K31/4402A61K31/381A61K31/341A61K31/277A61P35/00
CPCA61K31/277A61K31/341A61K31/381A61K31/4402C07C41/22C07C41/26C07C43/225C07C43/23C07C67/11C07C69/92C07C253/30C07C255/37C07C255/43C07D213/57C07D307/54C07D333/24
Inventor 田玉顺马军
Owner YANBIAN UNIV
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