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3-allyl-[1,1'-biphenyl]-4-phenol, derivatives, preparation methods and uses thereof
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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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[0010] At present, there is no biphenol compound with a new structure that has better anti-tumor effect than honokiol
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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 potassiumcarbonate (3.6g, 26mmol, 1.3equiv.) were added to 25ml of acetonesolvent 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 solidpotassiumcarbonate, 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% sodiumhydroxide solution, and wash with saturated saline Once, dried over anhydrousmagnesiumsulfate, and finally concentrated to obtain a colorless oily product (4.05g, 19.01mol, 95.03%).
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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 ...
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