Application of tanshinone II A derivative in drugs

A technology of tanshinone and derivatives, which is applied in the field of tanshinone derivatives, and can solve problems such as rarely reported applications

Inactive Publication Date: 2016-08-24
CHINA PHARM UNIV +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, tanshinone IIA is mostly used in the treatment of cardiovascular and cerebrovascular diseases, and its application in tumors and obesity is rarely reported.

Method used

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  • Application of tanshinone II A derivative in drugs
  • Application of tanshinone II A derivative in drugs
  • Application of tanshinone II A derivative in drugs

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052] Preparation of Compounds 3, 5, 7

[0053] Dissolve 580mg (2mmol) of tanshinone IIA in 20mL of dichloromethane, add 0.5mL of hydrobromic acid, add 0.15mL (1.95mmol) of liquid bromine, and react in the dark for 30min. After the reaction stopped, 30 mL of a saturated aqueous solution of sodium bisulfite was added, stirred for 10 min, washed with water, and dried over anhydrous sodium sulfate. Purified by column chromatography (PE:EA=36:1) to obtain compound 1. EI / MS (m / z): 372 (M + ).

[0054] 220mg (0.75mmol) of compound 1 was dissolved in 22mL of DMF, 0.3mL of triethylamine (2.3mmol), 0.16mL (1.5mmol) of ethyl acrylate, 38mg (0.15mol) of triphenylphosphine, 17mg (0.075mmol) of palladium acetate were added , heated at 100°C for 8 hours, after the reaction, filtered with suction to obtain the filtrate, added 20mLEA, washed with water, anhydrous Na 2 SO 4 dry. Purified by column chromatography (PE:EA=24:1) to obtain compound 3. 1 H NMR (300MHz, CDCl 3 ): 1.32 (9H, m...

Embodiment 2

[0058] Preparation of compound 10

[0059] Dissolve 372mg (1mmol) of compound 1 in 20mL of DMF, add 0.3mL of triethylamine (2.3mmol), 380mg (1.5mol) of triphenylphosphine, 170mg (0.75mmol) of palladium acetate, heat at 100°C for 16h and spin dry, add water 30mL, extracted with DCM, washed with water, anhydrous Na 2 SO 4 dry. Purified by column chromatography (PE / EA=36:1) to obtain compound 8.

[0060] Dissolve 140mg (0.38mmol) of compound 4 in 15ml of acetonitrile, heat and stir until dissolved, add selenium dioxide, heat the oil bath to 44°C and heat to reflux for 10h, cool to room temperature, filter with suction to obtain the filtrate, wash with 20ml of 5% NaOH solution 3 times, brine washing, anhydrous Na 2 SO 4 dry. Purified by column chromatography (PE / EA=12:1) to obtain compound 9.

[0061] 31mg (0.1mmol) of compound 5 was dissolved in 4mL of dichloromethane, 15mg (0.15mmol) of maleic anhydride, 0.03mL (0.3mmol) of triethylamine, a catalytic amount of DMAP were a...

Embodiment 3

[0063] Preparation of Compound 12

[0064] 117mg (0.4mmol) of tanshinone IIA was dissolved in 10mL of acetonitrile, 1.2mL (4.4mmol) of formaldehyde was added, 1d of acetic acid was reacted at reflux at 70°C for 30min, and purified by column chromatography (PE:EA=36:1) to obtain compound 11. 1 H NMR (300MHz, CDCl 3 ): 1.32 (6H, s, CH 3 ), 1.65 (2H, m, CH 2 ), 1.77 (2H, m, CH 2 ), 2.31 (3H, s, CH 3 ), 3.19 (2H, t, CH 2 ), 4.65 (2H, s, CH 2 ), 7.63 (2H, dd, Ar).

[0065]65 mg (0.2 mmol) of compound 11 was dissolved in 8 mL of dichloromethane, 60 mg (0.6 mmol) of maleic anhydride and 0.1 mL (0.6 mmol) of triethylamine were added, and stirred at room temperature for 12 h to stop the reaction. Purified by column chromatography (PE:EA=1:2) to obtain compound 12. (KBr)v max (cm -1 ): 2933.53, 2737.67, 2675.96, 2491.11, 1573.67, 1475.38, 1384.59, 1275.40, 1260.65, 1192.28, 875.61, 864.02. 1 H NMR (300MHz, DMSO-D 6 ): 1.32 (6H, s, CH 3 ), 1.65 (2H, m, CH 2 ), 1.77 (2H, m, ...

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Abstract

Tanshinone II A compounds are main lipid-soluble components of traditional Chinese medicine salviamiltiorrhiza btmge and have extensive pharmacological activity; the invention belongs to the technical fields of medicinal chemistry and drugs, and in particular, relates to the tanshinone II A derivatives (I), (II), (III) and (IV); the derivatives have good antitumor activity, and can be used for preparation of antitumor drugs.

Description

technical field [0001] The invention belongs to the technical field of medicinal chemistry and medicine, and in particular relates to a class of tanshinone derivatives, a pharmaceutical composition in which the derivatives are active ingredients, a preparation method thereof, and the drug application of the compound and other pharmaceutical compositions in tumors. Background technique [0002] Salviamiltiorrhiza Btmge belongs to the plant of the genus Salvia in the family Labiatae. As a traditional Chinese medicine, Salvia miltiorrhiza has been widely used in China, Japan and other regions, with a history of nearly 2,000 years of application, and is an important commodity in the domestic and foreign medicinal material markets. Salvia miltiorrhiza, alias red ginseng, purple danshen, blood danshen, was first recorded in the Eastern Han Dynasty "Shen Nong's Materia Medica", saying: "maintains evil spirits in the heart and subordinates, bowel sounds faint like running water, acc...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J73/00A61K31/58A61P35/00
Inventor 丁黎王进欣黄志鹏
Owner CHINA PHARM UNIV
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