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Tanshinone I derivative, preparation method and applications thereof

A technology of tanshinone and derivatives, applied in the field of pharmacy, can solve the problems of low bioavailability, poor water solubility of tanshinone I, low biological activity of tanshinone I and the like

Inactive Publication Date: 2016-06-01
SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] As one of the fat-soluble components of Salvia miltiorrhiza, tanshinone I has poor water solubility and low bioavailability in vivo. At present, there is no preparation directly made of tanshinone I for clinical application; in addition, the biological activity of tanshinone I is not high (usually IC 50 several to tens of μM), this is where the short board of Tanshinone I as drug development lies

Method used

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  • Tanshinone I derivative, preparation method and applications thereof
  • Tanshinone I derivative, preparation method and applications thereof
  • Tanshinone I derivative, preparation method and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] Embodiment 1, the synthesis of compound purple salvia miltiorrhiza

[0051]

[0052] Tanshinone I (1.38g, 5.0mmol) and selenium dioxide (1.10g, 10.0mmol) were added to 20mL dioxane / 6mL water, N 2 Protect and seal the tube at 110°C to avoid light for 72h. Stop the reaction, evaporate the solvent under reduced pressure, add 100 mL of water, extract three times with 100 mL of dichloromethane, combine the organic layers, wash with water and saturated brine in sequence, and dry over anhydrous sodium sulfate. After suction filtration, the filtrate was concentrated under reduced pressure, and the crude product was separated by column chromatography to obtain 0.38 g of a brown-red solid with a yield of 26%.

[0053] 1 HNMR (300MHz, CDCl 3 )δ9.26(d, J=8.9Hz, 1H), 8.35(d, J=9.1Hz, 1H), 7.85(d, J=8.7Hz, 1H), 7.67–7.51(m, 1H), 7.48( s,1H),7.39(d,J=7.0Hz,1H),4.71(d,J=7.7Hz,2H),3.50(t,J=7.0Hz,1H),2.71(s,3H). 13 CNMR (150MHz, CDCl 3 )δ 182.88, 176.02, 162.87, 141.39, 135.51, ...

Embodiment 2

[0054] Embodiment 2, the synthesis of compound S0

[0055]

[0056] Purple Danshen B (292mg, 1.0mmol) was added to 10mL of anhydrous dichloromethane, and PBr was added dropwise in an ice-water bath 3 (325mg, 1.2mmol) in dichloromethane solution, moved to room temperature to continue the reaction after dropping. After the reaction was detected by TLC, saturated sodium carbonate solution was added for extraction, and the organic layer was washed with water and saturated brine in sequence, and dried over anhydrous sodium sulfate. After suction filtration, the filtrate was concentrated under reduced pressure, and the crude product was separated by column chromatography to obtain 256 mg of a brown-red solid with a yield of 72%.

[0057] 1 HNMR (300MHz, CDCl 3 )δ9.28(d, J=8.7Hz, 1H), 8.36(d, J=8.6Hz, 1H), 7.85(d, J=8.6Hz, 1H), 7.65–7.52(m, 2H), 7.39( d,J=6.9Hz,1H),4.59(s,2H),2.71(s,3H). 13 CNMR (100MHz, CDCl 3 )δ 182.67, 174.79, 162.00, 144.29, 135.45, 134.09, 133.25, 132.9...

Embodiment 3

[0058] Embodiment 3, the synthesis of compound S1

[0059]

[0060] SO (18.2mg, 0.05mmol), morpholine (13.1mg, 0.15mmol) and potassium carbonate (23.0mg, 0.15mmol) were added into 0.4mL dichloromethane / 1.2mL acetonitrile and stirred at room temperature. After the reaction was detected by TLC, water was added for extraction, and the organic layer was washed with water and saturated brine in sequence, and dried over anhydrous sodium sulfate. After suction filtration, the filtrate was concentrated under reduced pressure, and the crude product was separated by column chromatography to obtain 19 mg of brown-red solid with a yield of 88%.

[0061] 1 HNMR (300MHz, CDCl 3 )δ9.21(d, J=8.7Hz, 0H), 8.27(d, J=8.6Hz, 1H), 7.78(d, J=8.6Hz, 1H), 7.56–7.49(m, 1H), 7.47( s,1H),7.33(d,J=6.6Hz,1H),3.80–3.65(m,4H),2.67(s,3H),2.53-2.63(m,4H). 13 CNMR (125MHz, CDCl 3 )δ 183.25, 175.39, 161.65, 143.56, 135.38, 133.89, 133.16, 132.88, 130.90, 129.58, 128.61, 124.91, 123.28, 122.79, 120.04, 11...

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Abstract

The present invention relates to a tanshinone I derivative represented by a general formula (I), wherein Z is OR1, NR2R3 or X. The present invention further relates to a preparation method of the tanshinone I derivative represented by the general formula (I), and uses of the tanshinone I derivative represented by the general formula (I) or a pharmaceutically acceptable salt thereof in preparation of drugs, particularly anti-tumor drugs. The general formula (1) is defined in the specification.

Description

technical field [0001] The invention belongs to the field of pharmacy, and relates to a tanshinone I derivative represented by general formula (I), a synthesis method thereof and an application in preparing antitumor drugs. Background technique [0002] Salvia miltiorrhiza is one of the traditional Chinese herbal medicines. Its fat-soluble components include tanshinone I, tanshinone IIA, tanshinone IIB, and cryptotanshinone. medicinal prospects. Among them, Tanshinone I (Tanshinone I, abbreviated as TanI) has a certain anti-tumor effect. Kuo-HsiungLee et al. reported that Tanshinone I had significant inhibitory effect on human breast cancer cells MCF-7 and MDA-MA-231 (J.Med.Chem.2004,47,5816-5819); JungJoonLee et al. found through research , Tanshinone I can inhibit the activation of human gastric adenocarcinoma cells AGS and human liver cancer cells Hep3B by inhibiting the activation of hypoxia-inducible factor-1 (J.Nat.Prod.2007,70,1093-1097); JohnH.K.Yeung et al. Tansh...

Claims

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Application Information

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IPC IPC(8): C07J73/00A61K31/58A61P35/00A61P35/02
Inventor 丁春勇宋姗姗焦明坤王迎庆缪泽鸿张翱
Owner SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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