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Phospholipid analog containing betulinic acid, preparation method and use

A technology of betulinic acid and analogs, which is applied in the field of betulinic acid-containing phospholipid analogs and antitumor drugs, can solve the problems of difficult absorption by the body and insoluble betulinic acid in water, etc.

Inactive Publication Date: 2017-10-20
HARBIN UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

It can solve the problem that betulinic acid is insoluble in water and difficult to be absorbed by the body

Method used

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  • Phospholipid analog containing betulinic acid, preparation method and use
  • Phospholipid analog containing betulinic acid, preparation method and use
  • Phospholipid analog containing betulinic acid, preparation method and use

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preparation example Construction

[0038] The preparation method of the phospholipid analog containing betulinic acid: after betulinic acid and succinic anhydride carry out oxygen acylation reaction, then react with corresponding 1-fatty acyl-Sn-glycerol-3-phosphocholine, Prepare corresponding betulinic acid-containing phospholipid analogs; the 1-fatty acyl-Sn-glycerol-3-phosphocholine is selected from 1-stearyl-Sn-glycerol-3-phosphocholine , 1-oleoyl-Sn-glycerol-3-phosphocholine, 1-palmitoyl-Sn-glycerol-3-phosphocholine.

[0039] The application of the phospholipid analogue containing betulinic acid in the preparation of antitumor drugs.

[0040] The phospholipid analog containing betulinic acid and the preparation method of the present invention are described in more detail in the following examples, but the examples do not constitute a limitation to the present invention.

Embodiment 1

[0041] Example 1 Preparation of 3-O-succinic acid monoyl betulinic acid

[0042]

[0043] Dissolve 4.57 grams (0.01 moles) of betulin in 200 milliliters of dichloromethane, add 5 milliliters of triethylamine, 0.98 grams (0.01 moles) of succinic anhydride, heat and reflux for 8 hours, cool, recover part of the solvent, and add 200 mL of ethanol, 3 mL of 5 mol / L hydrochloric acid aqueous solution, stirred for 1 hour, added ice water, precipitated a large amount of white solid, extracted with dichloromethane (100 mL × 3), washed with water, dried over anhydrous sodium sulfate, filtered, and evaporated Dichloromethane, the residue was subjected to silica gel column chromatography (dichloromethane: ethyl acetate = 1:1), and 3.82 g of milky white 3-O-succinoyl betulinic acid was obtained with a yield of 69%.

Embodiment 2

[0044] Example 2 1-Stearoyl-2-(3-O-succinyl betulinic acid) glycerol-3-phosphocholine (phospholipid analog containing betulinic acid)

[0045]

[0046] Dissolve 0.557 g (0.001 mol) of 3-O-succinoyl betulinic acid in 50 ml of dichloromethane, add 0.288 g (0.0015 mol) of 1-ethyl-(3-dimethylaminopropyl) carbon Diimine hydrochloride, 0.01 g of 4-dimethylaminopyridine, at room temperature, after stirring for 3 hours, add 0.523 g (0.001 mol) of 1-stearoyl-Sn-glycerol-3-phosphocholine, at room temperature , stirred for 48 hours, dichloromethane was distilled off under reduced pressure, the residue was washed 5 times with 10% citric acid aqueous solution, and silica gel column chromatography (methanol:chloroform:water=25:65:4) gave white 1-hard Fatty acyl-2-(3-O-succinyl betulinic acid) glycerol-3-phosphocholine 0.78 g (ie phospholipid analogs containing betulinic acid), yield 73%.

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Abstract

The invention provides a phospholipid analogue containing betulinic acid. The phospholipid analogue containing betulinic acid is shown in the formula (1) in the description, wherein R1 in the formula is selected from substances shown in the description. The invention further provides a preparing method of the phospholipid analogue and application of the phospholipid analogue in preparing anti-tumor drugs.

Description

technical field [0001] The invention relates to the fields of medicinal chemistry and therapeutics, in particular to a phospholipid analogue containing betulinic acid, a preparation method and its use as an antitumor drug. Background technique [0002] Betulinic acid (abbreviated as BA) (also known as betulinic acid, betulinic acid) is a needle crystal, molecular formula: CR 30 RHR 48 RO 3 , molecular weight 456.71, molecular structure formula: [0003] . [0004] Betulinic acid belongs to lupin-type pentacyclic triterpene compounds. Betulinic acid is a basic non-toxic anti-tumor compound. The semi-synthesis of betulinic acid as the lead compound has obtained derivatives with excellent biological activity. However, the water insoluble problem of betulinic acid derivatives has not been solved so far, which seriously hinders the popularization and application of betulinic acid derivatives in clinic. Some documents are given below for reference. [0005] PCT / US2005 / 0410...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07J63/00A61P35/00
CPCC07J63/008
Inventor 丁为民李雪薇李坤骐毕远桐白林涛谈东升
Owner HARBIN UNIV OF SCI & TECH