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Emodin derivates and application thereof in anti-cancer medicine preparation

A derivative, emodin technology, applied in the field of emodin derivatives and its application in the preparation of anticancer drugs, can solve the problem of insufficient anticancer activity of emodin, and achieve strong cytotoxicity

Inactive Publication Date: 2009-02-11
NANCHANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The active ingredient emodin, which has been isolated from various Chinese herbal medicines, has been confirmed to have certain anticancer activity, mainly by inhibiting the DNA synthesis of cancer cells. However, due to the insufficient anticancer activity of emodin, it has not been used clinically as a cancer drug use

Method used

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  • Emodin derivates and application thereof in anti-cancer medicine preparation
  • Emodin derivates and application thereof in anti-cancer medicine preparation
  • Emodin derivates and application thereof in anti-cancer medicine preparation

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Separation, extraction and purification of emodin (1).

[0019] Weigh 1Kg tiger stick, crush it through a 20-mesh sieve, use 95% industrial alcohol, reflux and extract twice on a water bath, combine the filtrate, concentrate under reduced pressure to 500ml, add 100-500ml of 3M sulfuric acid, reflux for 0.5-1h, then add 1500ml of water , standing overnight, and dried by suction to obtain 180g of pink powder. Put the obtained red powder into a Soxhlet extractor, and extract it with ether until the ether is nearly colorless in the Soxhlet extractor, first use 5% (w / w) NaHCO 3 solution (6×100ml), the ether layer was extracted, and the aqueous phase was discarded. 5% (w / w) Na 2 CO 3 Solution (8 × 100ml), extract the ether layer, 2 × 100ml of the extract before combining with 5Mol. Hydrochloric acid to adjust pH<4, filter, dry, and crystallize through acetone to obtain 2.75g of orange crystals of compound emodin (1), the product was obtained by Confirmed by IR, NMR, Ms an...

Embodiment 2

[0022] Preparation of Intermediate (2).

[0023] Weigh 2.1g (7.8mmol) emodin (1), 8g (28.6mmol) of anhydrous potassium carbonate after grinding, add 5ml (25mmol) of dimethyl sulfate, 190ml of acetone, stir for 16h, concentrate, add water and stir, filter, Wash with a small amount of cold acetone to obtain light yellow powder, 2.2g, yield 91.8%, melting point 226-228°C. 1H NMR (CDCl3 / TMS): δ: 2.46 (s, 3H), 3.95 (s, 3H,), 3.96 (s, 3H,), 3.98 (s, 3H,), 6.76 (d, J=2.5Hz, 1H), 7.09 (s, 1H,), 7.32 (d, J=2.5Hz, 1H), 7.64 (s, 1H,); IR (KBr), σ / cm-1: 3070, 2943, 2843, 1661, 1245; FAB-MS m / z (%): 313[M+H]+, elemental analysis (C 18 h 16 o 5 ): Found (calculated) / %: C 69.28 (69.23), H 5.10 (5.12).

Embodiment 3

[0025] Preparation of intermediates (3a) and (3b) mixed isomers.

[0026] Weigh 100 mg of compound (2), add 15 ml of glacial acetic acid, add 2 ml of HBr / AcOH, stir overnight at room temperature, precipitate precipitate, filter, and separate on a silica gel column (chloroform) to obtain 55 mg of orange-red crystals, yield 55%, melting point 194~ 196°C. 1H NMR (CDCl3 / TMS): δ: 2.43(s, 3H), δ 2.51(s, 3H), 3.91(s, 3H), 3.99(s, 3H), 4.03(s, 3H), 4.05(s, 3H), 6.70(d, J=2.5Hz, 1H), 6.79(d, J=2.5Hz, 1H), 6.07(s, 1H), 7.14(s, 1H), 7.30(d, J=2.5Hz, 1H), 7.46(d, J=2.5Hz, 1H), 7.57(s, 1H), 7.79(s, 1H), 13.08(s, 1H), 13.25(s, 1H); IR(KBr)σ / cm -1: 3074, 2946, 2845, 1734, 1677, 1345; FAB-MS m / z (%): 299[M+H]+, elemental analysis (C 17 h 14 o 5 ): Found (calculated) / %: C 68.55 (68.45), H 4.70 (4.73).

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Abstract

The invention relates to an emodin derivative and the application in preparing a anti-cancer drug, and the chemical structural formula of the emodin derivative of the invention is as shown in formula I, wherein, R1, R2, R3 are defined as described in the specification; the emodin and the derivative thereon provided by the invention are compounds which are prepared in a way that natural emodin is taken as the matrix, and then structural modification is carried out in accordance with the principles of drug molecules to design out the highly active compounds; experiments proof that the emodin derivative has obvious inhibitory effect on various tumor cells and can be used in preparing cancer-treatment drugs.

Description

Technical field [0001] The invention relates to emodin derivatives and their application in the preparation of medicines for treating cancer. Background technique [0002] Cancer has become one of the biggest diseases that threaten human health and quality of life. It is currently the most important strategy to use our country's rich natural resources to find pre-effective monomers and modify them to obtain highly efficient, highly selective, and low-toxicity anticancer drugs. The main research direction of anticancer drugs. [0003] The active ingredient emodin, which has been isolated from various Chinese herbal medicines, has been confirmed to have certain anticancer activity, mainly by inhibiting the DNA synthesis of cancer cells. However, due to the insufficient anticancer activity of emodin, it has not been used clinically as a Anticancer drug use. The Chinese invention patent ZL200310112459.2 of Gu Lianquan and others modified the 6-position and 8-position of emodin...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C225/36A61K31/135A61P35/00
Inventor 陆豫余勃姜伟伍晓春
Owner NANCHANG UNIV
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