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Tanshinone II A polymer compound and preparation and application thereof

The technology of a polymer compound and tanshinone, applied in the field of medicine, can solve the problem of dose-dependent inability to achieve effective treatment, and achieve the effect of significant pharmacological activity and good water solubility.

Inactive Publication Date: 2019-08-06
CHINA PHARM UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These side effects are often dose-dependent and cannot achieve effective treatment

Method used

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  • Tanshinone II A polymer compound and preparation and application thereof
  • Tanshinone II A polymer compound and preparation and application thereof
  • Tanshinone II A polymer compound and preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Embodiment 1: the preparation of 4-carboxy-butyl ester tanshinone IIA (WGZB-24)

[0022] Weigh 5g (17mmol) Tanshinone IIA, 5.6g (51mmol) SeO 2 In a 1L single-necked bottle, add 700-800 ml of acetonitrile as a solvent, reflux for 5-6 hours, stop heating and cool to room temperature, distill under reduced pressure to obtain a solid, dissolve the solid in dichloromethane and filter it with saturated ammonium chloride The solution was washed with the filtrate 2-3 times, dried over anhydrous sodium sulfate, and purified by column chromatography to obtain 1.32 g of red solid compound 2 with a yield of 25%.

[0023] Weigh 620mg (2mmol) of compound 2, 300mg (3mmol) of succinic anhydride in a 100ml single-necked bottle, dissolve with 30ml of anhydrous dichloromethane, add 0.83ml (6mmol) of triethylamine, vacuumize and protect with nitrogen, room temperature Stop the reaction after 30-40 minutes of reaction, wash the reaction solution 2-3 times with saturated ammonium chloride s...

Embodiment 2

[0025] Embodiment 2: Preparation of 4-carboxy-butyl ester tanshinone IIA-mPEG

[0026] Weigh 100mg (0.24mmol) of 4-carboxy-butyl tanshinone IIA, 220mg (0.29mmol) of mPEG with a molecular weight of 750, 74mg (0.36mmol) of DCC, 44mg (0.36mmol) of DMAP in a 100ml single-necked bottle, and use 40ml After anhydrous dichloromethane is dissolved, vacuumize and protect with nitrogen, react at 25-45°C for 24 hours, remove DCU by suction filtration, wash the filtrate 2-3 times with saturated ammonium chloride solution, dry over anhydrous sodium sulfate, and distill under reduced pressure Finally, a red oily substance was obtained. After dissolving the oily substance with a little dichloromethane, a large amount of diethyl ether was added under ice-bath conditions to form a precipitate. After suction filtration and drying, a red powdery solid compound 4-carboxy-butyl ester tanshinone IIA-mPEG was obtained. .

[0027] The spacer group obtained by the same method is C 1 -C 4 Straight-ch...

Embodiment 3

[0028] Embodiment 3: Preparation of 4-carboxy-butyl ester tanshinone IIA-PEG

[0029] Take by weighing 100mg (0.24mmol) 4-carboxy-butyl tanshinone IIA, 720mg (0.36mmol) PEG with a molecular weight of 2000, 74mg (0.36mmol) DCC, 44mg (0.36mmol) DMAP in a 100ml single-necked bottle, and use 45ml without After dissolving dichloromethane in water, vacuumize and protect with nitrogen, react at 25-45°C for 24 hours, remove DCU by suction filtration, wash the filtrate 2-3 times with saturated ammonium chloride solution, dry over anhydrous sodium sulfate, and distill under reduced pressure A red oil was obtained. After dissolving the oil with a little dichloromethane, a large amount of diethyl ether was added under ice-bath conditions to form a precipitate. After suction filtration and drying, the red powdery solid compound 4-carboxy-butyl tanshinone IIA-PEG was obtained.

[0030] The spacer group obtained by the same method is C 1 -C 4 Straight-chain unsaturated alkyl; C 1 -C 4 Br...

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Abstract

The invention specifically relates to a tanshinone II A polymer compound and application thereof in pharmacy, and belongs to the technical field of pharmacy. The tanshinone IIA polymer compound and anintermediate are characterized in that the structure of the tanshinone IIA polymer compound and the intermediate is shown in a formula (II), the tanshinone IIA polymer compound has good water solubility and remarkable pharmacological activity, and can be used for preparing drugs for preventing or treating the following diseases: cardiovascular and cerebrovascular diseases such as atherosclerosis,hyperlipidemia, cerebral ischemia, stroke, myocardial infarction, arrhythmia, angina pectoris, myocardial disease, myocardial hypertrophy and the like; Alzheimer's disease, early-onset Alzheimer's and other neurological diseases; liver diseases such as viral hepatitis and liver cirrhosis; and breast cancer, leukemia, liver cancer, colon cancer, melanoma and other cancers.

Description

[0001] The present invention is 201610479054.X, a divisional application of tanshinone IIA polymer compound and its preparation and application technical field [0002] The invention specifically relates to a tanshinone IIA macromolecule compound and its application in pharmacy, belonging to the technical field of medicine. Background technique [0003] The traditional Chinese medicine Salvia miltiorrhiza is widely used in the treatment of coronary heart disease and angina pectoris. As one of the most extracted components of Danshen, tanshinone IIA has anti-inflammatory, antioxidant and cytotoxic activities, as well as neuroprotective effects. However, the fatal flaw of tanshinone IIA is the low oral bioavailability. The reasons are as follows: first, the poor water solubility leads to poor absorption, which is inseparable from its structural characteristics. As a diterpenoid compound, Tanshinone IIA is a planar molecule with strong hydrophobicity, low polarity, almost inso...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G65/332C08G65/333A61K47/60A61K47/54A61K47/64A61K31/58A61P9/10A61P3/06A61P9/06A61P9/00A61P25/28A61P1/16A61P13/12A61P35/00A61P35/02
CPCA61P1/16A61P3/06A61P9/00A61P9/06A61P9/10A61P25/00A61P25/28A61P35/00A61P35/02C08G65/3328C08G65/33396
Inventor 王进欣赵丽宫志博丁黎尤启冬
Owner CHINA PHARM UNIV