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Mono-demethoxycurcumin pyrrole derivative and preparation method and application thereof

A technology for methoxy curcumin pyrrole and derivatives, which is applied in the field of mono-demethoxy curcumin pyrrole derivatives and their preparation, can solve the problems of insufficient research and complexity of the source problem, and achieve a good balance of physical and chemical properties , the effect of easy penetration

Pending Publication Date: 2019-05-31
石磊
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Also present in turmeric root are two analogues of curcumin: monodemethoxycurcumin and bisdemethoxycurcumin, which have the same extensive and significant biological activities as curcumin, but due to source issues has been understudied
Therefore, it is a complex task to improve the efficacy of drugs, especially those targeting the central brain system, by adjusting the lipid-water partition coefficient of the drug.

Method used

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  • Mono-demethoxycurcumin pyrrole derivative and preparation method and application thereof
  • Mono-demethoxycurcumin pyrrole derivative and preparation method and application thereof
  • Mono-demethoxycurcumin pyrrole derivative and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] The preparation of embodiment 1.4-hydroxyl-3-(pyrrolidinyl-1-methyl)benzaldehyde

[0020]

[0021] 5g of p-hydroxybenzaldehyde was dissolved in 50mL of water, then 3.07g of 40% formaldehyde solution was added, 2.9g of pyrrole was refluxed for 5 hours, cooled, and 5.1g of light yellow crystals were obtained by column chromatography, with a yield of 60.1%. 1 H NMR (CDCl 3 , 300MHz) δ: 9.87(s, 1H), 7, 63(m, 1H), 7.34(dd, 1H), 7.31(dd, 1H), 3.81(s, 2H), 2.56(m, 4H), 1.76 (m, 4H); ESI-MS m / z 203.1[M+H] + .

Embodiment 2

[0022] Example 2. Preparation of 6-(4-hydroxyl-3-(pyrrolidinyl-1-methyl)phenyl)hexane-5-ene-2,4-dione

[0023]

[0024] Dissolve 975mg of acetylacetone and 1g of boric anhydride in ethyl acetate, heat to reflux for half an hour, then add 1 equivalent of 2g of intermediate 1 and a catalytic amount of n-butylamine, reflux overnight, and column chromatography gives 2.1g of a light yellow product , yield 75%. 1 H NMR (CDCl 3 , 300MHz) δ: 9.89(s, 1H), 7.62, 6.63(dd, each 1H), 7.43(dd, 1H), 7.31(dd, 1H), 7.11(s, 1H), 6.53(s, 1H), 3.81(s, 2H), 2.55(m, 4H), 2.26(s, 3H), 1.85(m, 4H); ESI-MS m / z288.2[M+H] + .

Embodiment 3

[0025] Embodiment 3. Pyrrole monodemethoxy curcumin derivatives

[0026]

[0027] Dissolve 1g of intermediate 2 and 242mg of boric anhydride in ethyl acetate and reflux for half an hour, then add 1 equivalent of 530mg of 3-methoxy-4-hydroxybenzaldehyde and catalytic amount of n-butylamine, reflux for 24 hours, add 30mL of 1N hydrochloric acid After reflux for half an hour, the reaction solution was extracted with ethyl acetate, and column chromatography gave 0.9 g of the light yellow target product with a yield of 61.3%. 1 H NMR (CDCl 3 , 300MHz) δ: 9.5-8.0 (br, 1H), 7.52 (m, 3H), 7.29 (s, 1H), 7.19 (dd, 1H), 6.75 (m, 4H), 6.01 (s, 1H), 3.80 (s, 3H), 3.71(s, 2H), 2.36(m, 4H), 1.68(m, 4H); ESI-MS m / z 422.4[M+H] + .

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Abstract

The invention provides a mono-demethoxycurcumin pyrrole derivative as shown in a structural formula I. The compound has a good lipid-water partition coefficient, a good ability of penetrating a blood-brain barrier to target brain tissues, a good anti-glioma activity and safety and a good inhibition effect on human glioma U87, a tumor inhibition rate on nude mouse U87 glioma reaches 90% or above, and the mono-demethoxycurcumin pyrrole derivative can be used for preparing anti-glioma drugs.

Description

technical field [0001] The invention relates to the technical field of new drug research and development in medicinal chemistry, in particular to a novel monodemethoxycurcumin pyrrole derivative, a preparation method thereof and an application in antitumor. Background technique [0002] Curcumin is a chemical component extracted from the rhizomes of some plants in Zingiberaceae and Araceae. It is a diketone pigment with a wide range of pharmacological activities, mainly including anti-inflammatory, anti-oxidation, anti- Aging, anti-infection, hypolipidemic, anti-atherosclerosis and anti-tumor and other pharmacological activities. Also present in turmeric root are two analogues of curcumin: monodemethoxycurcumin and bisdemethoxycurcumin, which have the same extensive and significant biological activities as curcumin, but due to source issues has been understudied. In particular, monodemethoxycurcumin has been poorly studied due to its much lower content in curcuminoid root ...

Claims

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Application Information

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IPC IPC(8): C07D295/112A61K31/40A61P35/00
Inventor 石磊
Owner 石磊
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