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P-nitrophenoxy betulin (28) formyl ester and betulin derivatives synthesized therefrom, and preparation method and application thereof

A technology based on p-nitrophenoxy and betulin, which is applied in the direction of steroids, drug combinations, digestive system, etc., can solve the problems of poor water solubility, limited application and low bioavailability of betulin, and achieve high Bioavailability, good application prospects, mild reaction conditions

Active Publication Date: 2018-04-10
YANBIAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, betulin has defects such as poor water solubility and low bioavailability, which limit its application in clinical medicine.

Method used

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  • P-nitrophenoxy betulin (28) formyl ester and betulin derivatives synthesized therefrom, and preparation method and application thereof
  • P-nitrophenoxy betulin (28) formyl ester and betulin derivatives synthesized therefrom, and preparation method and application thereof
  • P-nitrophenoxy betulin (28) formyl ester and betulin derivatives synthesized therefrom, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0061] Weigh 100mg (0.23mmol) of betulin in a 25ml two-necked bottle, use 5ml of dry THF as a solvent, add 18μl (0.23mol) of pyridine as a catalyst, and add p-nitrate dissolved in THF (0.23mmol) dropwise under ice-bath conditions. 46 mg (0.23 mmol) of phenyl chloroformate, under nitrogen protection, and stirred at room temperature. TLC tracking reaction, until the betulin reaction is complete, stop stirring, evaporate the solvent under reduced pressure, silica gel column chromatography separation and purification, to obtain a white solid, which is p-nitrophenoxy betulinyl (28) formyl ester ( 77 mg, yield 55%).

[0062] The reaction equation is as follows:

[0063]

Embodiment 2

[0065] The synthetic steps of betulin derivative B-1:

[0066] Weigh 150mg (0.08mmol) of p-nitrophenoxy betulinyl (28) formyl ester in a 25ml single-necked bottle, add 10ml of dichloromethane as a solvent, then add 5μl (0.08mmol) aminoethanol, 27mg (0.22 mmol) 4-dimethylaminopyridine (DMPA) as a catalyst, nitrogen protection, stirring at room temperature. TLC tracking, after the complete reaction of p-nitrophenoxy betulinyl (28) formyl ester, stop stirring, evaporate the solvent under reduced pressure, separate and purify by silica gel column chromatography to obtain white solid B-1 (78 mg, yield 60 %).

[0067] The reaction equation is as follows:

[0068]

Embodiment 3

[0070] The synthetic steps of betulin derivative B-2:

[0071] Weigh 50mg (0.07mmol) p-nitrophenoxy betulinyl (28) formyl ester in a 25ml single-necked bottle, add 10ml dichloromethane as solvent, add 8μl (0.07mmol) N-aminomorpholine, 9mg (0.07mmol) 4-dimethylaminopyridine (DMPA) as a catalyst, stirred at room temperature under nitrogen protection. TLC tracking, after the complete reaction of p-nitrophenoxy betulinyl (28) formyl ester, stop stirring, evaporate the solvent under reduced pressure, separate and purify by silica gel column chromatography to obtain white solid B-2 (26 mg, yield 60 %).

[0072] The reaction equation is as follows:

[0073]

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Abstract

The invention discloses p-nitrophenoxy betulin (28) formyl ester and betulin derivatives synthesized therefrom, and a preparation method and an application thereof, and belongs to the technical fieldof pharmaceutical chemical. Four derivatives are synthesized with betulin as a matrix, that is to say, the tail end of a structure of the betulin is modified, a carbonacylation agent nitrophenyl chloroformate is introduced to a C-28 site, p-nitrophenoxy betulin (28) formyl ester is generated, and based on the p-nitrophenoxy betulin (28) formyl ester, four kinds of groups having biological activityand functionality are introduced. Specifically, with introduction of a structure of aminoethyl alcohol, the solubility is improved; with introduction of an N-amino morpholine group having a lysosomepositioning action and a triphenylphosphine active group having mitochondria targeted positioning, the product targetedly acts on cell organelles, the bioavailability is improved, and the higher biological activity is played; with introduction of a p-aminophenol structure, the synthesized compounds have certain antioxidant effects, and certain pharmacological activities are played by regulating the balance of redox in cells.

Description

technical field [0001] The invention belongs to the technical field of medicinal chemistry, and in particular relates to a p-nitrophenoxy betulinyl (28) formyl ester, a betulin derivative synthesized therefrom, a preparation method and an application. Background technique [0002] Betulin (Betulin) is a pentacyclic three-tiered compound, which mainly exists in birch bark, and its content is as high as 35%, making it easy to extract from nature. It has good activities in anti-inflammatory, anti-cancer, anti-virus, liver protection, liver protection and other aspects of regulating the immune function of the body, so it can be used as a research for drug development. However, betulin has defects such as poor water solubility and low bioavailability, which limit its application in clinical medicine. The chemical formula of betulin is as follows: [0003] Contents of the invention [0004] In response to the above problems, the present invention provides four betulin deriv...

Claims

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Application Information

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IPC IPC(8): C07J63/00A61P1/16
CPCC07J63/008
Inventor 金英今苗宇雷檬泽周鑫吴学
Owner YANBIAN UNIV
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