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Monocarbonyl curcumin analogue as well as preparation and application thereof

A technology of curcumin analogs and curcuminoids, applied in the field of medicine

Active Publication Date: 2021-09-07
THE AFFILIATED HOSPITAL OF TRADITIONAL CHINESE MEDICAL TO SOUTHWEST MEDICAL UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, there are still research gaps in MCACs

Method used

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  • Monocarbonyl curcumin analogue as well as preparation and application thereof
  • Monocarbonyl curcumin analogue as well as preparation and application thereof
  • Monocarbonyl curcumin analogue as well as preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Embodiment 1: Preparation of monocarbonyl curcuminoid analogs CuA-1~CuA-4

[0040] 1) The specific steps for preparing CuA-1~CuA-3 are as follows:

[0041] Dissolve 3.47 parts of aldehyde and 1.735 parts of ketone in 5 mL of saturated hydrogen chloride glacial acetic acid solution, and stir the reaction at room temperature for 12 hours to obtain solution I. After standing for 24 hours, filter solution I and treat it with pure water and absolute ethanol to obtain compound CuA-1, CuA-2 and CuA-3.

[0042] 2) The specific steps for preparing CuA-4 are as follows:

[0043] Take 28.4 parts of 3,4-dihydro-2H-pyran and 14.14 parts of vanillin in 0.16 parts of 4-pyridinium methylbenzenesulfonate dichloromethane suspension and react at room temperature for 12 hours to obtain solution II. After Ⅱconcentration, use saturated NaHCO 3 The solution was washed 3 times and washed with anhydrous Na 2 SO 2 Dry to obtain vanillin protectant;

[0044] Stir the ethanol solution of 3.4...

Embodiment 2

[0046] Preparation of monocarbonyl curcuminoid analogs CuA-1~CuA-4

[0047] 1) The specific steps for preparing CuA-1~CuA-3 are as follows:

[0048] Dissolve 5.2 parts of aldehyde and 1.735 parts of ketone in 5 mL of saturated hydrogen chloride glacial acetic acid solution, and stir the reaction at room temperature for 12 hours to obtain solution I. After standing for 24 hours, filter solution I and treat it with pure water and absolute ethanol to obtain compound CuA-1, CuA-2 and CuA-3.

[0049] 2) The specific steps for preparing CuA-4 are as follows:

[0050] Take 28.4 parts of 3,4-dihydro-2H-pyran and 14.14 parts of vanillin in 0.16 parts of 4-pyridinium methylbenzenesulfonate dichloromethane suspension and react at room temperature for 12 hours to obtain solution II. After Ⅱconcentration, use saturated NaHCO 3 The solution was washed 3 times and washed with anhydrous Na 2 SO 2 Dry to obtain vanillin protectant;

[0051] Stir the ethanol solution of 5.2 parts of vanilli...

Embodiment 3

[0052] Embodiment 3: Preparation of monocarbonyl curcuminoid analogs CuA-1~CuA-4

[0053] 1) The specific steps for preparing CuA-1~CuA-3 are as follows:

[0054] Dissolve 6.94 parts of aldehyde and 3.47 parts of ketone in 10 mL of saturated hydrogen chloride glacial acetic acid solution, and stir the reaction at room temperature for 24 hours to obtain solution I. After standing for 24 hours, filter solution I and treat it with pure water and absolute ethanol to obtain compound CuA-1, CuA-2 and CuA-3.

[0055] 2) The specific steps for preparing CuA-4 are as follows:

[0056] Take 56.8 parts of 3,4-dihydro-2H-pyran and 28.18 parts of vanillin in 0.32 parts of 4-pyridinium methylbenzenesulfonate dichloromethane suspension and react at room temperature for 24 hours to obtain solution II. After Ⅱconcentration, use saturated NaHCO 3 The solution was washed 3 times and washed with anhydrous Na 2 SO 2 Dry to obtain vanillin protectant;

[0057] Stir the ethanol solution of 6.9...

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Abstract

The invention discloses a monocarbonyl curcumin analogue as well as preparation and an application thereof, the curcumin analogue is represented by a formula I, or pharmaceutically acceptable salts of the curcumin analogue comprise hydrochloride and sulfate, aldehydes and ketones are used as raw materials, monocarbonyl curcumin analogues CuA-1-CuA-3 are designed and synthesized, by designing and synthesizing a monocarbonyl curcumin analogue CuA-4 by taking 3, 4-dihydro-2H-pyran, vanillin, 4-pyridinium methylbenzenesulfonate and 1-methyl-4-piperidone as raw materials, and substituting an unstable beta-dicarbonyl structure with a monocarbonyl group to obtain the more stable monocarbonyl curcumin analogue CuA-1-CuA-4. The monocarbonyl curcumin has better pharmacokinetic behavior and higher anti-tumor activity, and the monocarbonyl curcumin is applied to preparation of drugs for resisting inflammation and treating inflammation-related diseases, Alzheimer's disease, Parkinson's disease, depression, lung cancer, liver cancer, breast cancer, colon cancer and cervical cancer.

Description

technical field [0001] The invention relates to the technical field of medicine, in particular to a monocarbonyl curcuminoid analogue and its preparation and application. Background technique [0002] Natural medicine is an important source of new medicines, and it also provides ideas for the development of new structural medicines. Curcumin (Curcumin, CU), as one of the main active components of turmeric, has attracted widespread attention due to its significant antitumor activity. However, clinical research related to it has not made significant progress, mainly due to the poor stability and low bioavailability of curcumin. The instability and irregular metabolism of CU are mainly caused by the existence of β-dicarbonyl structural unit in its structure. Considering the "neighborhood effect" is also an effective strategy in the design of drug molecules to improve the anti-tumor activity of drugs. Representative monocarbonyl curcumin analogues EF24 and F35 exhibit high se...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/68C07D405/14A61K31/4412A61K31/4433A61P29/00A61P25/28A61P25/16A61P25/24A61P35/00
CPCC07D213/68C07D405/14A61P29/00A61P25/28A61P25/16A61P25/24A61P35/00Y02P20/55
Inventor 赵领魏郁梦皮超冯先虎邹永根沈宏萍侯益曾明唐文洁王元园马靖雯盛琳张小梅李柯赵文美
Owner THE AFFILIATED HOSPITAL OF TRADITIONAL CHINESE MEDICAL TO SOUTHWEST MEDICAL UNIV
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