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3-allyl-[1,1'-biphenyl]-4-phenol, derivatives, preparation methods and uses thereof

A technology of allyl and derivatives, applied in the field of chemical medicine

Active Publication Date: 2013-01-30
CHENGDU JINRUI FOUND BIOTECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] At present, there is no biphenol compound with a new structure that has better anti-tumor effect than honokiol

Method used

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  • 3-allyl-[1,1'-biphenyl]-4-phenol, derivatives, preparation methods and uses thereof
  • 3-allyl-[1,1'-biphenyl]-4-phenol, derivatives, preparation methods and uses thereof
  • 3-allyl-[1,1'-biphenyl]-4-phenol, derivatives, preparation methods and uses thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0137] Example 1 Preparation of 3-allyl-[1,1'-biphenyl]-4-phenol

[0138]

[0139] Step 1: Preparation of 1-allyloxy-4-bromobenzene

[0140] 4-Bromophenol (3.46g, 20mmol) and potassium carbonate (3.6g, 26mmol, 1.3equiv.) were added to 25ml of acetone solvent and stirred, then allyl bromide (1.9ml, 22mmol, 1.1equiv.) Slowly added dropwise to the reactor. The temperature was raised to a reflux state and the stirring was continued. After 5 hours of reaction, the reaction was terminated. After cooling down, filter out the solid potassium carbonate, evaporate the acetone from the reaction solution, extract the remaining solution three times with ether, each time 20 ml, wash the combined ether solution once with 20 ml of 10% sodium hydroxide solution, and wash with saturated saline Once, dried over anhydrous magnesium sulfate, and finally concentrated to obtain a colorless oily product (4.05g, 19.01mol, 95.03%).

[0141] Proton NMR spectrum (400MHz CDCl3): δ7.372(d, 2H, J=8.8Hz)...

Embodiment 2

[0156] Example 2 Preparation of 3-allyl-4'-methoxy-[1,1'-biphenyl]-4-phenol

[0157]

[0158] Ib

[0159] The preparation method is the same as in Example 1, the yield is 56.3%, and the identification data are as follows:

[0160] Proton NMR spectrum (400MHz, CDCl3): δ7.48-7.46 (m, 2H, Ar-H), 7.33-7.30 (m, 2H, Ar-H), 6.96-6.94 (m, 2H, Ar-H) , 6.86(d, 1H, J=8.4Hz, Ar-H), 6.11-6.01(m, 1H, -CH=CH2), 5.23-5.17(m, 2H, -CH=CH2), 3.84(s, 3H , 4-OCH3), 3.47 (d, 2H, J=5.4Hz, -CH2CH);

[0161] High resolution mass spectrum: 239.0994[M-H] - .

Embodiment 3

[0162] Example 3 Preparation of 3-allyl-3'-methoxy-[1,1'-biphenyl]-4-phenol

[0163]

[0164] The preparation method is the same as in Example 1, the yield is 51.9%, and the identification data are as follows:

[0165] Proton NMR spectrum (400MHz, CDCl 3 ): δ7.39-7.32(m, 3H, Ar-H), 7.15(d, 1H, J=7.6Hz, Ar-H), 7.09(s, 1H, Ar-H), 6.90-6.85(m, 2H, Ar-H), 6.08-6.04 (m, 1H, -C H =CH 2 ), 5.24-5.18 (m, 2H, -CH=C H 2 ), 3.87 (s, 3H, 3-OCH 3 ), 3.49 (d, 2H, J=6.4Hz, -C H 2 CH);

[0166] High resolution mass spectrum: 239.1005[M-H] - .

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Abstract

The present invention belongs to the field of chemical medicine, and particularly relates to 3-allyl-[1,1'-biphenyl]-4-phenol, derivatives, preparation methods and uses thereof. A technical problem solved by the present invention is to provide a new class of compounds: 3-allyl-[1,1'-biphenyl]-4-phenol represented by a formula I and derivatives thereof. Experiment results of the present invention show that 3-allyl-[1,1'-biphenyl]-4-phenol represented by the formula I and the derivatives thereof have good effects of anti-tumor, anti-angiogenesis, anti-oxidation and other disease resistance, and provide a new selection for drug preparation.

Description

technical field [0001] The invention belongs to the field of chemistry and medicine, and in particular relates to 3-allyl-[1,1'-biphenyl]-4-phenol derivatives and their derivatives as well as their preparation method and application. Background technique [0002] Among the biphenol compounds that have been reported so far, honokiol (honokiol) is more effective, and magnolol (Magnolol) is mainly used for cancer and inflammatory diseases. [0003] [0004] honokiol honokiol [0005] Studies by Wolfgang Schühly and others have shown that honokiol can inhibit COX-1, COX-2 and 5-LOX by 91%, 88% and 94% at a concentration of 8 μM, and its IC 50 1.8 μM, 2.1 μM and 4.2 μM, respectively. And the study found that the polarity of honokiol compounds plays an important role in antioxidant activity. [0006] Antioxidants can eliminate the endogenous active oxygen free radicals produced in the human body's aerobic metabolism, block the damage of excessive free radicals to human cell ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C39/21C07C37/00C07C43/23C07C41/26C07C323/18C07C319/20C07C39/373C07C205/20C07C201/12C07C311/08C07C303/40C07C233/25C07C231/12C07D317/54C07C43/215C07C43/225C07C41/16C07C205/35A61K31/05A61K31/085A61K31/10A61K31/09A61K31/055A61K31/18A61K31/167A61K31/36A61P35/00A61P29/00A61P19/02A61P1/00A61P27/02A61P3/10A61P17/06A61P9/10A61P39/06
Inventor 陈俐娟魏于全赖新天
Owner CHENGDU JINRUI FOUND BIOTECH CO LTD
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