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Resveratrol amide derivative and preparation method thereof

A technology of veratrol amide and retrol amide, which is applied in the field of medicine, can solve the problems of short metabolic cycle, side effects, and low anticancer activity, and achieve the effect of inhibiting growth

Inactive Publication Date: 2011-05-11
JIANGSU TIANSHENG PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Although resveratrol has good anticancer activity, it also has many disadvantages, such as many targets of action, which lead to some side effects; short metabolic cycle in the body, and cannot exert long-lasting and effective medicinal functions; anticancer relatively low activity

Method used

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  • Resveratrol amide derivative and preparation method thereof
  • Resveratrol amide derivative and preparation method thereof
  • Resveratrol amide derivative and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Example 1: Preparation of 3,5,4'-trimethoxy-2-carboxy resveratrol (compound 1)

[0024]

[0025] Add 20ml DMSO to a 50ml single-necked round bottom flask, add 3,5,4'-trimethoxy-2-formyl resveratrol (2.98g, 10mmol) under stirring, add NaH dropwise 2 PO 4 solution (0.5g NaH 2 PO 4 dissolved in 5ml water), stirred for 0.5h after the dropwise addition, and added NaClO dropwise 2 Solution (1.8g NaClO 2 dissolved in 20ml water), reacted at room temperature for 24h, and the reaction solution was poured into 5% NaHCO 3 In the solution, the aqueous phase was extracted with ethyl acetate, acidified with dilute hydrochloric acid, filtered, and the obtained solid was dissolved in dichloromethane, washed with saturated brine, dried, and recrystallized to obtain the target compound 3,5,4'-trimethoxy- 2-Carboxyresveratrol. Yield 72%, mp: 178-179°C. 1 H NMR (400MHz, CDCl 3 )δ (ppm): 3.78 (s, 6H), 3.85 (s, 3H), 6.54 (s, 1H), 6.91 (s, 1H), 6.92 (d, J=16.4, 1H), 6.97 (d, J =8....

Embodiment 2

[0026] Example 2: Preparation of (trans)-2,4-dimethoxy-6-(-4-methoxystyryl)-N-phenylbenzamide (compound 2)

[0027]

[0028] Add 10ml of methylene chloride in a 50ml single-necked round bottom flask, add aniline (0.102g, 1.1mmol) and 3,5,4'-trimethoxy-2-carboxy resveratrol (0.314g, 1.0mmol) successively, EDC.HCl (0.287g, 1.5mmol), HOBt (0.068g, 0.5mmol), after reaction at room temperature for 12h, the solvent was evaporated under reduced pressure, the obtained paste solid was dissolved in ethyl acetate, washed with saturated brine and dried The target compound 1 was obtained by column chromatography. Yield 77%, mp: 119-120°C. 1 H NMR (400MHz, CDCl 3 )δ (ppm): 3.83 (s, 6H), 3.87 (s, 3H), 3.92 (s, 3H), 6.44 (s, 1H), 6.83 (s, 1H), 6.87 (d, J=8.8, 2H ), 6.92 (d, J=8.4, 2H), 7.05 (d, J=16.4, 1H), 7.26 (d, J=16.4, 1H), 7.43-7.48 (dd, 3H), 7.51 (s, 1H) , 7.57 (d, J=8.8, 2H). MS (ESI): 390.16 (C 24 h 23 NO 4 ,[M+H] + ).Anal.Calcd for C 24 h 23 NO 4 : C, 74.02; H, 5.95; N...

Embodiment 3

[0029] Example 3: Preparation of (trans)-2,4-dimethoxy-N-(4-methoxyphenyl)-6-(-4-methoxystyryl)benzamide (compound 3)

[0030]

[0031] The preparation method is the same as in Example 2. Substitute p-methoxyaniline for aniline to obtain (trans)-2,4-dimethoxy-N-(4-methoxyphenyl)-6-(-4-methoxystyryl)benzamide . Yield 79%, mp: 76-97°C. 1 H NMR (400MHz, CDCl 3 )δ (ppm): 3.83 (s, 6H), 3.87 (s, 3H), 3.92 (s, 3H), 6.44 (s, 1H), 6.83 (s, 1H), 6.87 (d, J=8.8, 2H ), 6.92 (d, J=8.4, 2H), 7.05 (d, J=16.4, 1H), 7.26 (d, J=16.4, 1H), 7.43 (d, J=8.8, 2H), 7.51 (s, 1H), 7.57 (d, J=8.8, 2H). MS (ESI): 420.17 (C 25 h 25 NO 5 ,[M+H] + ).Anal.Calcd for C 25 h 25 NO 5 : C, 71.58; H, 6.01; N, 3.34%; Found: C, 71.79; H, 6.00; N, 3.33%.

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Abstract

The invention provides a novel resveratrol amide derivative for stopping tumor cells from multiplication. A general formula is shown in the specification, wherein the R refers to the novel resveratrol amide derivative has obvious restraining effect to epidermal cancel cell strains (KB) of the oral cavity of a human body and cell strains (K562) of human leukemia, thereby being capable of being used for preparing antineoplastic drug. The invention also discloses the preparation method of the novel resveratrol amide derivative.

Description

technical field [0001] The invention relates to a novel class of resveratrol amide derivatives and a preparation method thereof, as well as its use as an antitumor drug, belonging to the field of medicine. Background technique [0002] Resveratrol (resveratrol) is a non-flavonoid polyphenol natural product, which belongs to a kind of phytoalexin, and is a self-protection substance produced by higher plants when they are attacked by pathogens and in harsh external environments. Resveratrol has a variety of physiological activities, such as anti-cancer, cardiovascular protection and blood lipid-lowering effects, anti-oxidation and anti-free radical effects, liver protection and antibacterial effects. Anticancer effect is the most striking physiological activity of resveratrol. Various studies have confirmed that resveratrol has a significant inhibitory effect on various tumors such as nasopharyngeal cancer, lung cancer, liver cancer, colon cancer, gastric cancer, breast cance...

Claims

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Application Information

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IPC IPC(8): C07C235/64C07D213/75C07C235/60C07C231/02A61K31/167A61K31/4402A61K31/4406A61K31/166A61P35/00A61P35/02
Inventor 阮班锋王晓亮汤剑锋张燕滨杨永安
Owner JIANGSU TIANSHENG PHARMA
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