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Resveratrol benzene acrylamide derivative, preparing method and application thereof

A technology of alcohol phenylacrylamide and phenylacrylamide, applied in the field of resveratrol derivatives, can solve the problems that resveratrol cannot be used as an anticancer drug, photosensitivity and metabolic instability of resveratrol, etc.

Active Publication Date: 2012-08-01
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

[0004] However, due to the photosensitivity and metabolic instability of resveratrol, resveratrol itself cannot be used as an anticancer drug.

Method used

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  • Resveratrol benzene acrylamide derivative, preparing method and application thereof
  • Resveratrol benzene acrylamide derivative, preparing method and application thereof
  • Resveratrol benzene acrylamide derivative, preparing method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] Example 1: (E)-3-(2,4-dimethoxy-6-((E)-4-methoxystyrene)phenyl)-N-ethylacrylamide (Compound 1) preparation

[0049]

[0050] a. Add resveratrol 228mg (1mmol) and 10mL acetonitrile to the 50mL single-neck bottle, add DMF dropwise under magnetic stirring until the reaction solution changes from milky white turbidity to light yellow clear solution; then dropwise add phosphorus oxychloride 230mg under an ice-water bath (15mmol), stirred at room temperature for 30min after the dropwise addition; then reacted at 50°C for 3h, after the reaction was completed, filtered, dried, and subjected to column chromatography (ethyl acetate:petroleum ether=1:1 (volume)) to obtain ( E)-2,4-Dihydroxy-6-(4-hydroxystyrene)benzaldehyde (Intermediate I). Yellow solid, 95.7% yield. m.p.210-212℃; 1 H NMR (DMSO-d6): δ (ppm) 6.21 (s, 1H), 6.62 (s, 1H), 6.78 (d, 2H, J=8.4Hz), 7.02 (d, 1H, J=16.0Hz), 7.49(d, 2H, J=8.4Hz), 7.70(d, 1H, J=16.2Hz), 9.71(s, 1H), 10.27(s, 1H), 10.76(s, 1H), 12.12(s,...

Embodiment 2

[0054] Example 2: (E)-3-(2,4-dimethoxy-6-((E)-4-methoxystyrene)phenyl)-N-propylacrylamide (compound 2) preparation

[0055]

[0056] The preparation method is the same as in Example 1, except that in step d, propylamine is used instead of ethylamine to obtain the target product (E)-3-(2,4-dimethoxy-6-((E)-4-methoxyl group) Styrene)phenyl)-N-propylacrylamide. White solid, 83.1% yield, m.p.142-145°C; 1 H NMR (300MHz, CDCl 3 ): δ(ppm) 0.95(t, 3H, J=7.5Hz), 1.54-1.63(m, 2H), 3.33(q, 2H, J=6.6Hz), 3.83(s, 3H), 3.85(s, 3H), 3.87 (s, 3H), 5.55 (bras, 1H), 6.33 (d, 1H, J=15.6Hz), 6.40 (d, 1H, J=2.1Hz), 6.70 (d, 1H, J=2.1 Hz), 6.88-6.93(m, 3H), 7.28(d, 1H, J=15.9Hz), 7.44-7.46(m, 2H), 7.94(d, 1H, J=15.6Hz). MS(ESI): 382.5 (C 23 H 27 NO 4 , [M+H] + ).Anal.Calcd for C 23 H 27 NO 4 : C, 72.42; H, 7.13; N, 3.67%; Found: C, 72.30; H, 7.15; N, 3.68.

Embodiment 3

[0057] Example 3: Preparation of (E)-N-butyl-3-(2,4-dimethoxy-6-((E)-4-methoxystyrene))benzeneacrylamide (Compound 3)

[0058]

[0059] The preparation method is the same as in Example 1, except that in step d, butylamine is used instead of ethylamine to obtain the target product (E)-N-butyl-3-(2,4-dimethoxy-6-((E) -4-Methoxystyrene)) phenylacrylamide. White solid, 87.2% yield, m.p.153-155°C; 1 HNMR (300MHz, CDCl 3 ): δ(ppm) 0.93(t, 3H, J=7.2Hz), 1.34-1.41(m, 2H), 1.49-1.56(m, 2H), 3.34-3.40(m, 2H), 3.83(s, 3H) ), 3.85(s, 3H), 3.88(s, 3H), 5.49(bras, 1H), 6.32(d, 1H, J=15.6Hz), 6.41(d, 1H, J=2.4Hz), 6.70(d , 1H, J=2.4Hz), 6.88-6.93 (m, 3H), 7.28 (d, 1H, J=16.2Hz), 7.43-7.46 (m, 2H), 7.93 (d, 1H, J=15.6Hz) .MS(ESI): 396.5(C 24 H 29 NO 4 , [M+H] + ).Anal.Calcdfor C 24 H 29 NO 4 : C, 72.89; H, 7.39; N, 3.54%; Found: C, 72.73; H, 7.41; N, 3.55.

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Abstract

The invention discloses a resveratrol benzene acrylamide derivative, a preparing method and an application thereof. The resveratrol benzene acrylamide derivative has a structure shown in general formula (1) and general formula (2): the resveratrol benzene acrylamide derivative has an obvious effect of growth inhibition for a human body breast cancer cell line (MCF-7), a human body lung cancer cell line (A549) and a human body melanoma cell line (B16-F10), thereby the resveratrol benzene acrylamide derivative can be used for preparing antineoplastic drugs.

Description

1. Technical field [0001] The invention relates to a resveratrol derivative, in particular to a resveratrol phenylacrylamide derivative, a preparation method and use thereof. 2. Background technology [0002] Resveratrol (Res) is an anti-infective antibiotic secreted by plants in harsh environments or when they are attacked by pathogens. A large number of literatures report that resveratrol can prevent and alleviate a variety of diseases, including cancer, cardiovascular disease, pathogenic microorganism infection, phytoestrogen regulation, liver protection, liver benefit, prevention and treatment of senile dementia, senile degenerative diseases, etc. important application value. [0003] Resveratrol can inhibit or even reverse cancer. It was found that resveratrol inhibited the activity of RNA reductase in murine mast cell tumor cell P815 and human myeloid leukemia cell K562 by removing the tyrosyl group of small protein RNA reductase. Resveratrol can not only inhibit DN...

Claims

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Application Information

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IPC IPC(8): C07C235/34C07C235/36C07C235/38C07C231/02C07C231/10C07D207/06C07D211/16C07D211/36C07D307/52C07D295/13C07D295/182A61K31/165A61K31/167A61K31/341A61K31/40A61K31/445A61K31/495A61K31/5375A61K31/54A61P35/00
Inventor 阮班锋管秋香姚日生李绪奇邓胜松
Owner 黄山市开发投资集团有限公司
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