Tanshinone derivative, preparation method and application thereof

A technology of tanshinone and compound, applied in the field of novel tanshinone derivatives, can solve the problems of absorption, transport limitation, low bioavailability and the like

Active Publication Date: 2016-08-24
上海维京生物医药科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] However, tanshinone I is a fat-soluble component, insoluble in water, its absorption and transport in the body are limite

Method used

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  • Tanshinone derivative, preparation method and application thereof
  • Tanshinone derivative, preparation method and application thereof
  • Tanshinone derivative, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0019] Example 1. Synthesis of compound 2

[0020]

[0021] Dissolve 5 g of raw material tanshinone I-2-formaldehyde and 2 g of Boc-amine in 50 ml of dry acetonitrile solution, add 4 g of triethylsilane at room temperature, add 2 ml of trifluoroacetic acid, and react under nitrogen protection, stirring at 25 degrees for 16 hours, The reaction solution was poured into 200ml saturated sodium bicarbonate solution, extracted twice with 100ml dichloromethane, the combined dichloromethane layers were washed twice with 200ml water, once washed with 200ml brine, dried, and concentrated under reduced pressure. The crude product was chromatographed on a silica gel column to obtain 5.3 g of Compound 2. LC-Ms: ESI: 406.2

[0022] 1 H NMR (300MHz, CDCl 3 )δ9.02(d, J=8.2Hz, 1H), 7.60(d, J=8.8Hz, 1H), 7.50-7.45(m, 1H), 7.30-7.24(m, 2H), 6.72(s, 1H ), 4.43(d, J=4.8Hz, 2H), 2.20(s, 3H), 2.18(s, 3H), 1.32(s, 9H)

example 2

[0023] Example 2. Synthesis of compound 3

[0024]

[0025] 5 g of compound 2 was dissolved in 50 ml of dichloromethane, 15 ml of trifluoroacetic acid was added dropwise in an ice bath, stirred at 20 degrees Celsius for 5 hours, and concentrated under reduced pressure to obtain 5.1 g of compound 3. The product was directly used in the next reaction without purification.

example 3

[0026] Example 3: Synthesis of Compound 4

[0027]

[0028] Add 100 mg of compound 3 and 100 mg of triethylamine to anhydrous dichloromethane, add 50 mg of acetic anhydride dropwise in an ice bath, and stir at room temperature for 0.5 hours. The reaction solution was washed once with saturated brine, dried, and concentrated under reduced pressure. The crude product was subjected to silica gel column chromatography to obtain 92 mg of product 4. LC-Ms: ESI: 348.2

[0029] 1 H NMR (300MHz, CDCl 3 )δ9.09(d, J=8.8Hz, 1H), 7.64(d, J=8.7Hz, 1H), 7.55-7.46(m, 1H), 7.32-7.24(m, 2H), 6.77(s, 1H ), 4.46(d, J=4.8Hz, 2H), 2.45(s, 3H), 2.23(s, 3H), 2.18(s, 3H).

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Abstract

The invention relates to a tanshinone I derivative, a preparation method and application thereof. The compound is a furan ring 2-substituted amide methylene modifier in the structural formula of tanshinone I, tanshinone I serves as the raw material, and the novel tanshinone derivative is prepared through a chemical synthesis method and can be used for treating cancers, serving as a tumor multi-drug resistance reversing agent, assistant medicine and a CYP1 family specific inhibitor, treating cardiovascular and cerebrovascular diseases, serving as a carboxylesterase inhibitor, treating androgen related diseases and serving as antibacterial.

Description

technical field [0001] The invention discloses a class of novel tanshinone derivatives, its preparation method and its application Background technique [0002] Salvia miltiorrhiza is the root of Salvia genus Lamiaceae, also known as red ginseng, purple salvia miltiorrhiza, and blood salvia miltiorrhiza. The Eastern Han Dynasty "Shen Nong's Materia Medica" listed it as top grade. Tanshinone is a component of the ether extract of the root of the traditional Chinese medicine Salvia miltiorrhiza, and it is the main effective part of Danshen. After a large number of pharmacological, toxicological, active ingredients and clinical studies, it has been proved that tanshinone has definite curative effects on various diseases and has low toxicity. Tanshinone I is one of the main active ingredients in tanshinone, which is a fat-soluble cherry red needle crystal. It contains a quinone structure, which is easily oxidized and reduced, and can participate in various biochemical reaction...

Claims

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Application Information

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IPC IPC(8): C07J73/00A61P35/00A61P35/02A61P31/00A61P9/00A61P5/24A61P43/00
Inventor 栾德刚秦立玙栾松平
Owner 上海维京生物医药科技有限公司
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