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Tanshinone IIA derivate comprising polyethylene glycol group and preparation and application of tanshinone IIA derivate

A technology of ethylene glycol-based double salvia and triethylene glycol-based double salvia, applied in the field of medicine, can solve problems such as low bioavailability, achieve significant anti-cancer activity, and significantly treat cardiovascular and cerebrovascular diseases.

Inactive Publication Date: 2015-11-11
SHIJIAZHUANG UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, tanshinone IIA is insoluble in water and has low bioavailability in the body. There has been no pharmaceutical preparation made directly from tanshinone IIA for clinical use, which limits its application.

Method used

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  • Tanshinone IIA derivate comprising polyethylene glycol group and preparation and application of tanshinone IIA derivate
  • Tanshinone IIA derivate comprising polyethylene glycol group and preparation and application of tanshinone IIA derivate
  • Tanshinone IIA derivate comprising polyethylene glycol group and preparation and application of tanshinone IIA derivate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] Preparation of ethylene glycol-based bistanshinone IIA (1)

[0018] The structure of compound (1) is shown below:

[0019]

[0020] Tanshinone IIA (2.94g, 10mmol) was dissolved in 15mL redistilled DMF, after cooling in an ice bath, POCl was added dropwise 3 (2.28g, 15mmol), remove the ice bath, react overnight at room temperature, after the reaction is complete, pour into 30mL ice water, extract with ethyl acetate 15mLх3, water 15mLх2, NaHCO 3 Solution 15mLх2, saturated saline 15mLх2 washing, anhydrous Na 2 SO 4 Dry, filter, concentrate, and purify by silica gel column chromatography to obtain 16-formyltanshinone IIA with a yield of 45%.

[0021] 16-Formyltanshinone IIA (3.22g, 10mmol) was dissolved in 25mL methanol and 12mL dichloromethane mixed solvent, under ice cooling, add NaBH 4 (0.76g, 20mmol), reacted for 20 minutes, slowly added 12mL of water, aliquoted methanol and dichloromethane, the aqueous layer was extracted with ethyl acetate 10mLх3, anhydrous Na ...

Embodiment 2

[0024] Preparation of Diethylene Glycol Bistanshinone IIA (2)

[0025] The structure of compound (2) is shown below:

[0026]

[0027] 16-Hydroxymethyltanshinone IIA (3.24g, 10mmol) was dissolved in 20mL of anhydrous dichloromethane, diethylene glycol (0.63g, 6mmol) was added, and other operations were the same as in Example 1 to obtain compound (2), Yield 43%. 1 HNMR (400MHz, CDC1 3 )δ: 7.60(d, J =8.1Hz,2H), 7.46(d, J =8.1Hz, 2H), 5.07(s, 4H), 3.62(t, J =6.2Hz,8H),3.05(m,4H),2.20(s,6H),1.77-1.79(m,4H),1.63-1.66(m,4H),1.29(s,12H).

Embodiment 3

[0029] Preparation of Triethylene Glycol Bistanshinone IIA (3)

[0030] The structure of compound (3) is shown below:

[0031]

[0032] 16-Hydroxymethyltanshinone IIA (3.24g, 10mmol) was dissolved in 20mL of anhydrous dichloromethane, triethylene glycol (0.90g, 6mmol) was added, and other operations were the same as in Example 1 to obtain compound (3), Yield 40%. 1 HNMR (400MHz, CDC1 3 )δ: 7.60(d, J =8.1Hz,2H), 7.46(d, J =8.1Hz, 2H), 5.07(s, 4H), 3.61(t, J =6.2Hz,12H),3.05(m,4H),2.20(s,6H),1.77-1.79(m,4H),1.63-1.66(m,4H),1.29(s,12H).

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Abstract

The invention relates to a tanshinone IIA derivate comprising a polyethylene glycol group and preparation and application of the tanshinone IIA derivate. The tanshinone IIA derivate comprising the polyethylene glycol group and the preparation and application of the tanshinone IIA derivate have the benefits as follows: the provided novel tanshinone IIA derivate can be used for treatment of cardiovascular and cerebrovascular diseases; the tanshinone IIA derivate comprising the polyethylene glycol group has better water solubility and can enter the blood-brain barrier, therefore the curative effect is improved, and the bioavailability of the tanshinone IIA derivate is greatly improved.

Description

technical field [0001] The invention relates to a derivative of tanshinone IIA and its application in pharmacy, belonging to the technical field of medicine. Background technique [0002] Salvia miltiorrhiza is the root and stem of Salvia miltiorrhiza, which has the effects of dispelling blood stasis and relieving pain, promoting blood circulation and stimulating menstruation, clearing the heart and eliminating troubles. It is mainly used clinically for cardiovascular and cerebrovascular diseases. The chemical composition of Salvia miltiorrhiza is divided into water-soluble phenolic acids and fat-soluble diterpene quinones. Tanshinone IIA is one of the fat-soluble components of Danshen, which has a wide range of pharmacological effects and can be used clinically for the treatment of many diseases. However, tanshinone IIA is insoluble in water and has low bioavailability in vivo. There has been no pharmaceutical preparation made directly from tanshinone IIA for clinical use,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J73/00A61P9/00
CPCC07J73/003
Inventor 张宝华史兰香刘斯婕郭瑞霞
Owner SHIJIAZHUANG UNIVERSITY
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