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Honokiol series derivates, preparation and use thereof

A technology of phenol derivatives and magnolia bark, applied in the field of medicinal chemistry, to achieve excellent anti-tumor activity

Active Publication Date: 2008-10-08
CHENGDU JINRUI FOUND BIOTECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0019] Taking a comprehensive view of the research on the structural analogues of honokiol at home and abroad, it can be clearly found that the research on the structural analogues of honokiol prepared by the total synthesis method is in-depth and meticulous, but the research on the derivatization of honokiol as raw materials is scarce. There are reports

Method used

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  • Honokiol series derivates, preparation and use thereof
  • Honokiol series derivates, preparation and use thereof
  • Honokiol series derivates, preparation and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] Example 1 3', the preparation of 5-diallyl-2,4'-dihydroxybiphenyl-3-aldehyde (Ia)

[0046] Dissolve 7g of sodium hydroxide in 20ml of water, add 0.266g of honokiol, use tetrabutylammonium bromide as a phase transfer catalyst, then raise the temperature of the oil bath to 65°C, slowly add 0.3ml of chloroform dropwise, and the reaction time is 2h , lower the reaction product to room temperature, adjust the pH value to 6-7 with 6mol / l hydrochloric acid, add 10ml of distilled water, stir well and extract 3 times with chloroform, combine the organic phases, wash 2 times with saturated saline, anhydrous sulfuric acid Distilled under reduced pressure after sodium drying to obtain a mixture of brown oily products.

[0047] The mixed product was separated by high-speed countercurrent chromatography, mobile phase: n-hexane-ethyl acetate, stationary phase: methanol-water, mobile phase flow rate 2ml / min, rotation speed 850rpm, sample concentration 20mg / mL, sample volume: 20ml, dete...

Embodiment 2

[0062] Example 2 3', the preparation of 5-diallyl-2,4'-dihydroxybiphenyl-3-oxime (IIa)

[0063] Add 0.1mmol of 3`,5-diallyl-2,4`-dihydroxybiphenyl-3-aldehyde (Ia) and 2ml of methanol into a 25ml reaction tube, place it in an EYELA synthesizer at a temperature of 25°C, and stir to make it Dissolve, add 1 mmol of hydroxylamine hydrochloride, adjust the pH to 8 with triethylamine, and stir at 25°C for 1 hour. Add 15 ml of distilled water, filter, wash with distilled water, and dry the filter cake in a vacuum oven to obtain a yellowish solid powder with a yield of 88%.

[0064] with mass spectrometry, 1 H NMR and 13 C NMR identification product, the experimental data are as follows:

[0065] 1 H NMR (400MHz, d 6 -DMSO), δ (ppm): 11.64 (s, 1H), 10.41 (s, 1H), 9.52 (s, 1H), 8.39 (s, 1H), 7.24 (q, J=2.0, 8.0Hz, 1H) , 7.22(d, J=2.0Hz, 1H), 7.14(d, J=2.0Hz, 1H), 7.06(d, J=2.0Hz, 1H), 6.86(d, J=8.0Hz, 1H), 5.91 -6.04(m, 2H), 5.00-5.11(m, 4H), 3.33(t, J=6.4, 11.2Hz, 4H);

[0066]...

Embodiment 3

[0068] The preparation of embodiment 3 honokiol derivative IIb

[0069] Add 0.1mmol of 3`,5-diallyl-2,4`-dihydroxybiphenyl-3-aldehyde (Ia) and 2ml of methanol into a 25ml reaction tube, place it in an EYELA synthesizer, control the temperature at 25°C, and stir Make it dissolve, add 0.2 mmol of cyclocitamine, adjust the pH value to 8 with triethylamine, and stir at 25°C for 1 hour. Add 15 ml of distilled water, filter the resulting precipitate, wash with distilled water, and dry the filter cake in a vacuum oven to obtain a yellowish solid powder with a yield of 85%.

[0070] with mass spectrometry, 1 H NMR and 13 C NMR identification product, the experimental data are as follows:

[0071] 1 H NMR (400MHz, CDCl 3 ), δ(ppm): 8.37(s, 1H), 7.40(q, J=1.6, 5.6Hz, 1H), 7.36(d, J=1.6Hz, 1H), 7.17(d, J=1.6Hz, 1H) , 7.01(d, J=1.6Hz, 1H), 6.86(d, J=5.6Hz, 1H), 5.94-6.09(m, 2H), 5.15-5.22(m, 2H), 3.47(d, J=4.0 Hz, 2H), 3.36(d, J=4.0Hz, 2H), 3.24(s, 1H), 1.36-1.82(m, 10H);

[0072]...

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Abstract

The invention relates to magnolola derivatives, the preparation method thereof, medical compounds with the magnolola derivatives as active components, as well as the application of the medical compounds in cancer treatment, pertaining to the technical field of pharmaceutical chemistry. The magnolola derivatives of the invention mainly include 3-substituted derivatives of magnolola; wherein the magnolola derivative with the formula I a is an intermediate product; the structural formula of the magnolola derivatives is II, wherein R1 is one of the following: H, halogen, hydroxyl, cyano, nitryl, amidocyanogen, alkyl, halogenated alkyl, cyanogens alkyl, hydroxide alkyl, allyl, amide, alkyloxyacyl, alkoxy, thiol group, alkyl, phenyl or heterocyclic radical. Cell poison tests and anti-tumor cell tests show that the magnolola derivatives have good anti-tumor effects.

Description

technical field [0001] The invention relates to honokiol series derivatives and a preparation method thereof, a pharmaceutical composition with honokiol derivatives as active ingredients, and the application of the pharmaceutical composition in treating cancer, belonging to the technical field of medicinal chemistry. Background technique [0002] Honokiol is the active ingredient purified and isolated from the traditional Chinese medicine Magnolia officinalis. Modern medical research shows that honokiol has a variety of pharmacological effects, including anti-oxidation, antithrombotic, antibacterial, neurotrophic activity, anti-anxiety, anti-inflammatory and antitumor effects. Also, the magnolol (a in the figure below) purified and separated from the traditional Chinese medicine Magnolia officinalis is an isomer of honokiol (b in the figure below), and its pharmacological effect is not as strong as that of honokiol. [0003] [0004] Utilize the rich resources of Chinese...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C47/57C07C45/30C07C39/21C07C37/11C07C251/48C07C249/08C07C255/41C07C253/30C07D311/04C07D261/20A61K31/05A61K31/11A61K31/42A61K31/352A61P29/00A61P35/00
Inventor 陈俐娟魏于全罗有福徐咏斌胡佳师键友
Owner CHENGDU JINRUI FOUND BIOTECH CO LTD
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