Glycyrrhetinic acid derivative and its preparation method and use

A technology of glycyrrhetic acid and derivatives, which can be used in drug combinations, pharmaceutical formulations, steroids, etc., can solve problems such as poor water solubility and poor bioavailability, and achieve the effects of improving antitumor activity and inhibiting adverse reactions.

Active Publication Date: 2020-09-11
陈懿 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the poor water solubility of glycyrrhetinic acid, resulting in poor bioavailability, clinical application requires large doses, and long-term large-scale medication will cause adverse reactions such as drug-induced hypertension and edema.

Method used

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  • Glycyrrhetinic acid derivative and its preparation method and use
  • Glycyrrhetinic acid derivative and its preparation method and use
  • Glycyrrhetinic acid derivative and its preparation method and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] Example 1. PEG 350 Synthesis of monomethyl ether glycyrrhetinic acid (GTA-mPEG 350 )

[0049]

[0050] Glycyrrhetinic acid (330mg, 0.7mmol) and PEG 350 Monomethyl ether (compound represented by formula (4) where n is 8 and R is methyl, 280 mg, 0.8 mmol) was dissolved in 40 mL of dichloromethane. EDC-HCl (153 mg, 0.8 mmol) and DMAP (9.4 mg, 0.08 mmol) were added sequentially, and stirred at room temperature for 14 hours. After the reaction was complete, aqueous hydrochloric acid (0.1N, 50 mL) was added, stirred at room temperature for 10 minutes, and then extracted with dichloromethane (20 mL) for a total of three extractions. The extracts were combined and washed with saturated brine (30 mL). Anhydrous Na was added to the organic phase 2 SO 4 After drying, the organic solvent is distilled off under reduced pressure after filtration, and the thick product is separated through silica gel chromatography (eluent is V 石油醚 :V 乙酸乙酯 :V 乙酸 =20:10:1) to get the compou...

Embodiment 2

[0051] Example 2. PEG 400 Glycyrrhetinic acid (GA-I-PEG 400 )

[0052]

[0053] Synthesize according to the synthesis method of Example 1. use PEG 400 (n is 9 and R is the compound shown in the formula (4) of H) replaces the PEG of embodiment 1 350 monomethyl ether. Compound GTA-PEG 400 The yield is 75%.

Embodiment 3

[0054] Example 3.PEG 1000 Glycyrrhetinic acid (GTA-PEG 1000 )

[0055] Synthesize according to the synthesis method of Example 1. use PEG 1000 (n is 23 and R is the compound shown in the formula (4) of H) replaces the PEG of embodiment 1 350 monomethyl ether. Compound GTA-PEG 1000 Yield 70%.

[0056]

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Abstract

The disclosure provides a glycyrrhetinic acid derivative. The glycyrrhetinic acid derivative has a structure shown as formula (1), wherein n is an integer of 7-35; and R is H or methyl. On the other hand, the invention also discloses a preparation method of the glycyrrhetinic acid derivative. The method includes: in an organic solvent, and in the presence of a catalyst and a dehydrating agent, contacting glycyrrhetinic acid with a substance shown as formula (2) under esterification reaction conditions. The invention also provides the use of the glycyrrhetinic acid derivative in preparation ofdrugs treating tumors. Through the above technical scheme, the glycyrrhetinic acid derivative provided by the invention has greatly improved solubility and more optimized lipid-water partition coefficient, therefore, the in-vivo anti-tumor activity of the glycyrrhetinic acid derivative can be greatly improved compared with glycyrrhetinic acid, and various adverse reactions probably caused by glycyrrhetinic acid preparations can be effectively inhibited.

Description

technical field [0001] The disclosure relates to the field of medicinal chemistry, in particular, to a glycyrrhetinic acid derivative, a method for preparing a glycyrrhetinic acid derivative, a glycyrrhetinic acid derivative prepared by the method, and uses of the glycyrrhetinic acid derivative. Background technique [0002] Malignant tumors are currently one of the leading causes of death worldwide, and have become a major category of diseases that seriously endanger human life and health and restrict social and economic development. Statistics show that in recent years, the mortality rate of malignant tumors among Chinese residents has increased by 83% compared with the mid-1970s. The development of effective antitumor drugs to inhibit the growth of malignant tumors is an important technical problem that needs to be solved urgently in the field of medicine. [0003] Glycyrrhetinic acid (GTA) has a variety of pharmacological activities, including anti-inflammatory, anti-ul...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07J63/00A61K31/56A61K31/77A61P35/00C08G65/332
CPCA61K31/77C07J63/008C08G65/3324C08G2650/04C08G2650/10
Inventor 陈懿吴飞鹏
Owner 陈懿
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