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Alizarin aminophosphonate derivatives and their synthesis method and use

A technology of alizarin aminophosphonate and aminophosphonate, which is applied in the field of alizarin aminophosphonate derivatives and their synthesis, and can solve problems such as no public reports of α-aminophosphonate

Inactive Publication Date: 2015-07-01
GUANGXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there is no public report on the introduction of α-aminophosphonate functional group derivatives into alizarin and the antitumor effects of such derivatives.

Method used

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  • Alizarin aminophosphonate derivatives and their synthesis method and use
  • Alizarin aminophosphonate derivatives and their synthesis method and use
  • Alizarin aminophosphonate derivatives and their synthesis method and use

Examples

Experimental program
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Effect test

Embodiment 1

[0059] Example 1: O, O'diethyl{[2-(1-hydroxy-9,10-dioxo-9,10-dihydroanthracene-2-oxymethyl)propionylamino](4-bromo Synthesis of diethyl phenyl)methyl}phosphonate (a)

[0060] 1) Synthesis of diethyl α-O, O'diethylamino(4-bromophenyl)methylphosphonate

[0061] Add p-bromobenzaldehyde, ammonium acetate and diethyl phosphite (2:1:1 molar ratio) in a round bottom flask, stir and react at 80°C for 10 hours, then add the amount of diethyl ether into the round bottom flask is 1.2 times the amount of p-bromobenzaldehyde), concentrated hydrochloric acid was added under ice bath to make the reaction system acidic (pH=6) and stirred for 3h, the reaction system was extracted with water, the aqueous layer was collected and extracted with ether to remove organic impurities, Collect the water layer again, and in the water layer of collection, add the sodium hydroxide solution that mass concentration is 10% and adjust its pH to be 9, extract with ethyl acetate, collect the organic layer, the...

Embodiment 2

[0069] Example 2: O, O'diethyl{[2-(1-hydroxy-9,10-dioxo-9,10-dihydroanthracene-2-oxymethyl)propionylamino](2-bromo Synthesis of diethyl phenyl)methyl}phosphonate (b)

[0070] 1) Synthesis of diethyl α-O, O'diethylamino(2-bromophenyl)methylphosphonate

[0071] Synthesize according to the method and conditions described in step 1) in Example 1, except that p-bromobenzaldehyde is replaced with o-bromobenzaldehyde.

[0072] 2) Synthesis of target product:

[0073] 2.1) with embodiment 1;

[0074] 2.2) In a round bottom flask, dissolve 1 mmol 2-(1-hydroxy-9,10-dioxo-9,10-dihydroanthracen-2-yloxy)propionic acid in 10 mL N,N-dimethyl In formamide, add 0.1 mmol catalyst 1-hydroxybenzotriazole dropwise under ice bath, stir at room temperature for 3 min, then add 1.5 mmol condensing agent 1-(3-dimethylaminopropyl)-3-ethylcarbodiethylene Amine hydrochloride, continue to stir for 13min; Add dropwise 1mmolα-O, O' diethylamino (2-bromophenyl) methylphosphonic acid diethyl ester (with 5m...

Embodiment 3

[0079] Example 3: O, O'diethyl{[2-(1-hydroxy-9,10-dioxo-9,10-dihydroanthracene-2-oxymethyl)propionylamino](3-bromo Synthesis of diethyl phenyl)methyl}phosphonate (c)

[0080] 1) Synthesis of diethyl α-O, O'diethylamino(3-bromophenyl)methylphosphonate

[0081] Synthesize according to the method and conditions described in step 1) in Example 1, except that m-bromobenzaldehyde is used instead of p-bromobenzaldehyde.

[0082] 2) Synthesis of target product:

[0083] 2.1) with embodiment 1;

[0084] 2.2) In a round bottom flask, dissolve 1mmol of 2-(1-hydroxy-9,10-dioxo-9,10-dihydroanthracen-2-yloxy)propionic acid in 10mL of methanol, under ice bath Add 0.05 mmol of catalyst 1-hydroxybenzotriazole dropwise, stir at room temperature for 5 min, then add 2 mmol of condensing agent 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, and continue stirring for 3 min; Then add 1mmol α-O, O'diethylamino (3-bromophenyl) methylphosphonic acid diethyl ester (dissolved in 20mL of ...

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Abstract

The invention discloses alizarin aminophosphonate derivatives and their synthesis method and use. The synthesis method comprises that alizarin and 2-bromopropionic acid as raw materials are dissolved in a polar solvent, the solution undergoes a reaction in the presence of potassium hydroxide as an acid binding agent to produce 2-(1-hydroxy-9, 10-dioxo-9,10-dihydroanthracene-2-yloxy)propionic acid, the 2-(1-hydroxy-9,10-dioxo-9,10-dihydroanthracene-2-yloxy)propionic acid and alpha-aminophosphonate as raw materials are dissolved in a polar solvent, the solution undergoes a full reaction in the presence of 1-hydroxybenzotriazole as a catalyst and 1-(3-dimethylaminopropyl)-3-ethyl-carbodiimide hydrochloride as a condensing agent, trichloromethane is added into the reaction produce solution, a water washing process is carried out, and an organic layer is collected and then is subjected to chromatography purification by a silicagel column. The alizarin aminophosphonate derivatives have a general structural formula (I).

Description

technical field [0001] The invention relates to alizarin derivatives, in particular to alizarin aminophosphonate derivatives and their synthesis method and application. Background technique [0002] Alizarin (Alizarin, chemical name is 1,2-dihydroxy 9,10-anthraquinone), since alizarin was extracted and purified from the root of madder, alizarin and its derivatives have been used in total synthesis, structural modification, and biological activity. research has aroused widespread concern. Existing studies have shown that alizarin has specific hypoglycemic, anti-inflammatory, antibacterial, and antiviral effects, and it has also been reported that alizarin has certain antitumor activity. [0003] α-Aminophosphonate is an intermediate compound with biological activity and pharmaceutical activity, and has been widely used in antibiotics, fungicides, enzyme inhibitors and herbicides. However, there are no public reports on the introduction of α-aminophosphonate functional group...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/40A61K31/662A61P35/00
Inventor 王恒山潘英明姚贵阳叶鳗仪黄日镇
Owner GUANGXI NORMAL UNIV
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