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Resveratrol analogue and preparation method and application thereof

A technology of resveratrol and analogues, which is applied in the field of medicinal compounds and its preparation, can solve problems such as elevation and achieve excellent antioxidant activity

Inactive Publication Date: 2011-08-17
JINAN UNIVERSITY +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Under normal conditions, ROS are produced at a rate that does not exceed the ability of tissues to metabolize them, but under certain conditions, ROS can rise to levels that exceed these protective mechanisms

Method used

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  • Resveratrol analogue and preparation method and application thereof
  • Resveratrol analogue and preparation method and application thereof
  • Resveratrol analogue and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Preparation of 2-(2,4-dihydroxy-6-(4-hydroxystyryl)benzylidene)-hydrazinothioamide (1a)

[0034] The reaction equation is as follows:

[0035]

[0036] 256 mg (1 mmol) ( E )-2,4-dihydroxy-6-(4-hydroxystyryl) 256 mg (1 mmol) of benzaldehyde was dissolved in absolute ethanol solution, and 112 mg (1.5 mmol) of hydrochloride of thiosemicarbazide was added, Heat to reflux and stir for 2 h, evaporate part of the ethanol, add appropriate amount of Na 2 CO 3 Neutralize HCl, filter, wash with water, and separate by ethyl acetate / petroleum ether (1:2) column chromatography to obtain 180 mg of a light blue solid with a yield of 54.7%.

[0037] ESI-MS: 320.1[M+H] + ; 1 H NMR (DMSO- d 6 ): 2.08 (s, 2 H), 6.24 (d, 1 H , J = 1.8 Hz), 6.56 (t, 1 H, J = 6.9 Hz), 6.78 (d, 2 H, J = 8.7 Hz), 6.85 (s, 1 H), 6.90 (s, 1 H), 7.31 (s, 1 H), 7.42 (d, 2 H, J = 24 Hz), 8.67 (s, 1 H), 9.63 (s, 1 H ), 11.16 (s, 1 H); elemental analysis: C 16 h 15 N 3 o 3 S. h 2 O Found (%): C 55....

Embodiment 2

[0039] Preparation of 2-(2-hydroxy-6-(4-hydroxystyryl)-4-methoxybenzylidene)-hydrazinothioamide (1b)

[0040]

[0041] As shown in Example 1, the difference is to use ( E )-2-Hydroxy-4-methoxy-6-(4-hydroxystyryl)benzaldehyde (270 mg, 1 mmol) instead of ( E )-2,4-dihydroxy-6-(4-hydroxystyryl)benzaldehyde. 283 mg of a light blue solid was obtained, and the yield was 85%.

[0042] ESI-MS: 334.2[M+H] + ; 1 H NMR (DMSO- d 6 ): 3.78 (s, 3 H), 6.26 (d, 1 H, J = 1.8 Hz), 6.58 (d, 1 H, J = 2.1 Hz), 6.89 (s, 1 H), 6.97 (d, 2 H , J = 6.6 Hz), 7.44 (d, 1 H, J = 12 Hz), 7.54 (d, 2 H, J = 8.5 Hz), 8.06 (s, 1 H), 8.67 (d, 1 H), 9.95 (s , 1 H), 10.04 (s, 1 H), 11.18 (s, 1 H).

Embodiment 3

[0044] Preparation of 2-(2-hydroxy-4-methoxy-6-(4-methoxystyryl)benzylidene)-hydrazinothioamide (1c)

[0045]

[0046] As shown in Example 1, the difference is to use ( E )-2-Hydroxy-4-methoxyl-6-(4-methoxystyryl)benzaldehyde (284mg, 1mmol) instead of ( E )-2,4-dihydroxy-6-(4-hydroxystyryl)benzaldehyde. Pale yellow solid, 325 mg, yield 91%.

[0047] ESI-MS: 358.3[M+H] + , 1 H NMR (DMSO- d 6 ): 3.79 (s, 6H), 6.42 (s, 1H), 6.72 (s, 1H), 6, 96 (d, 2H, J = 8.5 Hz), 7.05 (d, 2 H, J = 15 Hz), 7.43 (d, 2 H, J = 8.5), 7.49 (d, 1 H), 7.69 (s, 1 H), 8.45 (s, 1 H), 11.46 (s, 1H); elemental analysis: C 18 h 19 N 3 o 3 S Found (%): C 59.88, H 5.59, N 11.62%. Theoretical (%): C 60.49, H 5.36, N 11.76.

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Abstract

The invention discloses a resveratrol analogue and a preparation method and application thereof to treatment of diseases related to aging and SIRTI enzyme activity. The resveratrol analogue disclosed by the invention has an eliminating effect on DPPH radical (DPPH.), superoxide anion radical (O2<.->), hydroxide anion radical (OH.) and nitrogen peroxide radical (OHOO.) and has excellent antioxidation activity. Some derivatives of the resveratrol analogue are SIRTI enzyme activating agents while others are excellent SIRT1 enzyme inhibitors.

Description

technical field [0001] The invention relates to a medicinal compound and its preparation method and application, in particular to a resveratrol analogue and its preparation method and application. Background technique [0002] In the process of oxygen metabolism, the human body will produce a variety of reactive oxygen species free radicals (ROS), and the human body also has a variety of mechanisms to inactivate ROS. Under normal conditions, ROS are not produced at a rate that exceeds the ability of tissues to metabolize them, but under certain circumstances ROS can rise to levels that exceed these protective mechanisms. At this time, too much ROS will attack proteins, fats and DNA, causing cell and tissue damage, causing the body to age, leading to various diseases, such as stroke, ischemia-reperfusion, cardiovascular disease, cancer and neurological diseases including Alzheimer's disease. Haimer's disease, Parkinson's disease, Hodgkin's disease, etc. [0003] Silent info...

Claims

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Application Information

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IPC IPC(8): C07C335/40C07C251/30C07C249/02C07C211/28C07C211/27C07C209/22C07C39/21C07C37/00C07D215/42A61K31/175A61K31/15A61K31/137A61K31/065A61K31/4706A61P39/06A61P25/00A61P9/10A61P9/00A61P35/00A61P25/28A61P25/16
Inventor 王玉强于沛刘伟刘铭程潜任俊兰
Owner JINAN UNIVERSITY
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