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Rhein aminophosphonate derivatives, and synthetic method and applications thereof

A technology of rhein aminophosphonate and acid aminophosphonate, which is applied in the direction of drug combination, chemical instrument and method, medical preparations containing active ingredients, etc., and can solve the problem that there is no public report on α-aminophosphonate and other issues, to achieve the effect of good medicinal value

Inactive Publication Date: 2014-01-22
GUANGXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are no public reports on the introduction of α-aminophosphonate functional groups into rhein and the anti-tumor effects of such derivatives.

Method used

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  • Rhein aminophosphonate derivatives, and synthetic method and applications thereof
  • Rhein aminophosphonate derivatives, and synthetic method and applications thereof
  • Rhein aminophosphonate derivatives, and synthetic method and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0057] Example 1: O, O'diethyl{[2-(4,5-dihydroxy-9,10-dioxo-9,10-dihydroanthraceneamino)acetamido](4-bromophenyl) Synthesis of Diethyl Methyl}phosphonate (a)

[0058] 1) Synthesis of diethyl α-O, O'diethylamino(4-bromophenyl)methylphosphonate

[0059] 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 organic...

Embodiment 2

[0066] Example 2: O, O'diethyl{[2-(4,5-dihydroxy-9,10-dioxo-9,10-dihydroanthraceneamino)acetamido](2-bromophenyl) Synthesis of Diethyl Methyl}phosphonate (b)

[0067] 1) Synthesis of diethyl α-O, O'diethylamino(2-bromophenyl)methylphosphonate

[0068] Synthesize according to the method and conditions described in step 1) in Example 1, except that p-bromobenzaldehyde is replaced with o-bromobenzaldehyde.

[0069] 2) Synthesis of target product:

[0070] In a round bottom flask, dissolve 1 mmol rhein in 10 mL N,N-dimethylformamide, add 0.1 mmol catalyst 1-hydroxybenzotriazole dropwise under ice-cooling, stir at room temperature for 3 min, then add 1.5 mmol Mixture 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, continue to stir for 13min; then add dropwise 1mmol α-O, O'diethylamino (2 -Bromophenyl)methylphosphonic acid diethyl ester (dissolved with 5mL dimethyl sulfoxide to form a solution, added as a solution), stirred at room temperature until the reaction was ...

Embodiment 3

[0075] Example 3: O, O'diethyl{[2-(4,5-dihydroxy-9,10-dioxo-9,10-dihydroanthracenylamino)acetamido](3-bromophenyl) Synthesis of Diethyl Methyl}phosphonate (c)

[0076] 1) Synthesis of diethyl α-O, O'diethylamino(3-bromophenyl)methylphosphonate

[0077] Synthesize according to the method and conditions described in step 1) in Example 1, except that m-bromobenzaldehyde is used instead of p-bromobenzaldehyde.

[0078] 2) Synthesis of target product:

[0079] In a round bottom flask, dissolve 1mmol rhein in 10mL methanol, add dropwise 0.05mmol catalyst 1-hydroxybenzotriazole under ice bath, stir at room temperature for 5min, then add 2mmol condensing agent 1-(3-dimethylamino Propyl)-3-ethylcarbodiimide hydrochloride, continue to stir for 3min; then add 1mmol α-O, O'diethylamino(3-bromophenyl)methylphosphonic acid dropwise to the round bottom flask Diethyl ester (dissolved with 20mL ethanol to form a solution, added as a solution), stirred at room temperature until the reaction ...

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Abstract

The invention discloses a series of rhein aminophosphonate derivatives, and a synthetic method and applications thereof. The synthetic method of the rhein aminophosphonate derivatives comprises: taking rhein and an alpha-aminophosphonate as raw materials, dissolving in a polar solvent, in the presence of a catalyst HOBT and a condensing agent EDAC, reacting completely; and adding trichloromethane into the reaction liquid, washing with water, collecting the organic layer, applying to silica gel for column chromatography, eluting with a mixed solvent of ethyl acetate and petroleum ether with a volume ratio of 1:4-100 to obtain the corresponding derivative. The rhein aminophosphonate derivatives have the structural general formula (I) as shown in the description, wherein R is p-bromophenyl, o-bromophenyl, m-bromophenyl, p-fluorophenyl, o-fluorophenyl, p-chlorophenyl, m-chlorophenyl, o-chlorophenyl, m-methoxyphenyl, o-methoxyphenyl, phenyl, naphthyl, p-methoxyphenyl, m-methylphenyl, p-methylphenyl, m-fluorophenyl or anthryl.

Description

technical field [0001] The invention relates to rhein derivatives, in particular to rhein aminophosphonate derivatives and their synthesis method and application. Background technique [0002] Rhein (Rhein, whose chemical name is 1,8-dihydroxy-3-carboxyanthraquinone), derived from Polygonaceae plants, is the main component of medicinal rhubarb, rhubarb palmatum, and the rhizome of Polygonum multiflorum. Since 1844, Schossberger etc. extracted and purified rhein for the first time from rhubarb, the research on rhein and its derivatives in total synthesis, structural transformation and biological activity has attracted widespread attention. Existing studies have shown that rhein has specific hypoglycemic, anti-inflammatory, antibacterial, and antiviral effects, and there are also public reports that rhein is used to treat diabetic nephropathy. The invention patent with publication number CN102060809A discloses a rhein derivative and the application of such derivative in the t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/40A61K31/662A61P35/00
Inventor 王恒山黄日镇潘英明姚贵阳戴伟龙叶鳗仪陈振锋
Owner GUANGXI NORMAL UNIV
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