3-hydroxy-4,3',4',5'-tetromethoxy bibenzyl phosphate and its composition, prepn and application

A technology of methoxyphenyl and p-methoxybenzene, applied in the direction of phosphorus organic compounds, etc., can solve problems such as poor water solubility, and achieve the effects of less environmental pollution, low reaction cost, and simple post-treatment

Inactive Publication Date: 2005-12-14
GUANGZHOU INST OF GEOCHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

It can be predicted that erianin, as a natural product with a new mechanism of action and significant anti-tumor activity, has potential application prospects, but its water solubility is poor and it is difficult to administer it through blood vessels

Method used

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  • 3-hydroxy-4,3',4',5'-tetromethoxy bibenzyl phosphate and its composition, prepn and application
  • 3-hydroxy-4,3',4',5'-tetromethoxy bibenzyl phosphate and its composition, prepn and application
  • 3-hydroxy-4,3',4',5'-tetromethoxy bibenzyl phosphate and its composition, prepn and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Take 10.2g (0.061mol) of p-methoxyphenylacetic acid in a three-necked flask, add 20mL of glacial acetic acid to dissolve it, then add 3.6mL of bromine (11.2g, 0.068mol) dropwise, drop it for 45 minutes, and then stir in an ice bath 1 hour, poured into ice water, precipitated solid, filtered, and dried to obtain 14.8 g of 3-bromo-4-methoxy-phenylacetic acid, the yield was 98.3% (the literature value was 98%), and the mixture was weighed with ethanol-water White flaky crystals were obtained by crystallization with a yield of 70% and a melting point of 113-114°C (literature value of 113-114°C).

[0045]Weigh 4.92g (0.02mol) of the obtained 3-bromo-4-methoxyphenylacetic acid, and add 4.32g (0.022mol) of 3,4,5-trimethoxybenzaldehyde into the reaction flask, and use 20mL Acetic anhydride was dissolved, and 5.0 mL of triethylamine was added dropwise, heated to 130°C, and reacted for 5 hours. After acidification with concentrated hydrochloric acid, it was poured into ice water...

Embodiment 2

[0050] Embodiment 2: Inhibitory test to mouse P388 leukemia cells

[0051] Press 10 -6 mol / L 3-hydroxyl-4,3',4',5'-tetramethoxybibenzyl phosphate disodium salt prepared in Example 1 was applied to mouse P388 leukemia cells for 72 hours, and the inhibition of tumor cells The rate reaches 75% to 90%.

Embodiment 3

[0052] Embodiment 3: To the human HL-60 leukemia cell inhibition test

[0053] Press 10 -8 mol / L 3-hydroxyl-4,3 ', 4', 5'-tetramethoxybibenzyl phosphate disodium salt prepared in Example 1 was applied to human HL-60 leukemia cells for 72 hours, and the effect on tumor cells The inhibition rate is between 99% and 100%.

[0054] Embodiment 2~3 is the test that we entrust National Center for New Drug Screening to do. The test results of Examples 2-3 show that 3-hydroxy-4,3',4',5'-tetramethoxybibenzyl phosphate has very strong antitumor activity.

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Abstract

The present invention relates to 3-hydroxy-4, 3', 4', 5'-tetrmethoxy bibenzyl phosphate shown in the general expression, and its composition, preparation process and application in treating tumor. The present invention prepares water soluble 3-hydroxy-4, 3', 4', 5'-tetrmethoxy bibenzyl phosphate through the first Perkin condensation to constitute stibene skeleton; catalytic hydrogenation with Raney-Ni catalyst after functional group conversion to obtain 3-hydroxy-4, 3', 4', 5'-tetrmethoxy bibenzyl; reaction with phosphorylating reagent under the action of acid binding agent, water washing, and mixing with alkali while heating to obtain 3-hydroxy-4, 3', 4', 5'-tetrmethoxy bibenzyl phosphate. Initial pharmacological research shows that the compound as precursor medicine has excellent water solubility and pharmacokinetic property and excellent antitumor activity and may be used in treating tumor.

Description

technical field [0001] The present invention relates to 3-hydroxyl-4,3',4',5'-tetramethoxy bibenzyl phosphate, especially to water-soluble 3-hydroxyl-4,3',4',5'-tetramethyl Oxybibenzyl phosphate salt, and also relates to the composition, preparation method and application of the compound in the treatment of tumors. Background technique [0002] 3-Hydroxy-4,3′,4′,5′-tetramethoxybibenzyl, also known as erianin, and its English name is erianin, is a polyhydroxybibenzyl compound present in the traditional Chinese herbal medicine Dendrobium chrysalis natural product. A large number of biological activity studies have shown that erianin has strong anti-tumor activity, especially has a significant inhibitory effect on the proliferation of human leukemia HL-60 cells, and its effect is significantly better than the anti-tumor drug vincristine (Li Y M , Wang H Y, Liu G Q. Acta Pharmacol Sin, 2001, 22(11): 1018.). Recently, the in vitro and in vivo activity of erianin as an antivasc...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/09
Inventor 邹永钟荣清张学景王志新何树杰
Owner GUANGZHOU INST OF GEOCHEMISTRY - CHINESE ACAD OF SCI
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