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Hydroxyanthraquinone derivatives and their application in preparation of anticancer medicines

A technology of hydroxyanthraquinones and derivatives, applied in the field of hydroxyanthraquinones derivatives, can solve the problem of insufficient anti-tumor activity and achieve strong cytotoxicity

Inactive Publication Date: 2004-11-17
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

For example, it has inhibitory effect on the growth of human proleukocyte (HL-60), mouse sarcoma, mouse liver tumor and other tumor strains, [Edited by Huang Taikang, Commonly Used Chinese Herbal Medicine Components and Pharmacological Handbook, P1225, 1994, China Medical Science and Technology Publishing Society]. But because the antitumor activity of natural hydroxyanthraquinone compounds is not high enough, they cannot be used clinically as anticancer drugs at present

Method used

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  • Hydroxyanthraquinone derivatives and their application in preparation of anticancer medicines
  • Hydroxyanthraquinone derivatives and their application in preparation of anticancer medicines
  • Hydroxyanthraquinone derivatives and their application in preparation of anticancer medicines

Examples

Experimental program
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Effect test

Embodiment 1

[0021] Example 1: Extraction, separation and purification of natural hydroxyanthraquinone compounds emodin and emodin methyl ether

[0022] 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 it under reduced pressure to 500ml, add 100-500ml of 3Mol. water, stand overnight, and dry by suction filtration to obtain 180g pink powder. Put the obtained red powder into a Soxhlet extractor and extract with ether until the ether is close to colorless in the Soxhlet extractor. )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 merging was adjusted to PH3 and elemental analysis data.

[0023] Emodin, orange-red needle-like crystals, m.p.254-256℃IR(KBr).3300, 1675, 1625; 1 H NMR (DMSO-d 6 / TMS, 500 MHz) δ: 2.351(s, 3H), 6.503(d, J=...

Embodiment 2

[0026] Embodiment two: the preparation of intermediate product (3)

[0027] Weigh 4.2g (15.6mmol) emodin, anhydrous K after grinding 2 CO 3 16g (28.6mmol), add Me 2 SO 4 5ml (50mmol), 380ml of acetone, stirred and refluxed for 5-20h, concentrated, stirred with water, filtered, washed with a small amount of cold acetone to obtain 4.4g of light yellow powder (3), yield 90.5%. Product structure by IR, MMR, M 3 and elemental analysis data. m.p. 225-227°C, IR(KBr)v: 1661, 1600, 1564, 1321, 1245. 1 H NMR (CDCl 3 / TMS, 500MHz) δ: 2.467(s, 3H), 3.950(s, 3H), 3.962(s, 3H), 3.984(s, 3H), 6.763(d, J=2.5, 1H), 7.094(s, 1H), 7.320(d, J=2.5, 1H), 7.640(s, 1H); FAB-Ms m / z 313[M+1] + ;Anal.Calcd for C 18h 16 o 5 : C 69.22, H 5.16, found C 69.31, H 5.12.

Embodiment 3

[0028] Embodiment three: the preparation of intermediate product (4)

[0029] Weigh 4.0g (6.4mmol) and 2.0g (3.5mmol), 1,3-dibromo-5,5-dimethylcaprolactin (BDH), add 200-500ml CCl 44 , after thermally dissolving, add 0.6g benzoyl peroxide, stir and reflux for 6-15h, filter, wash the solid with hot water twice, dry, and separate by silica gel column chromatography (ethyl acetate:benzene=10:90) to obtain Light yellow powder (4) 2.8g, yield 56.0%. Product structure by IR, MMR, M 3 and elemental analysis data. m.p 250-252℃, IR(KBr)υ: 1665, 1597, 1334, 1245; 1 HNMR (CDCl 3 / TMS, 500MHz) δ: 3.962(s, 3H), 3.971(s, 3H), 4.023(s, 3H), 4.523(s, 2H), 6.779(d, J=2.5, 1H), 7.309(s, 1H), 7.328(d, J=2.5, 1H), 7.832(s, 1H); FAB-Ms m / z 391[M+1] + ;Calcd for C 18 h 15 BrO 5 : C 55.26, H 3.86, found C 55.38, H 3.83.

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Abstract

The invention relates to hydroxy anthraquinone derivatives and their use in preparing anti-cancer medicament, test has shown that the hydroxy anthraquinone derivatives have appreciable inhibitory action for various tumor cell strains, thus can be used in preparing cancer treatment medicament. The chemical structural formula of the hydroxy anthraquinone derivatives is shown by I, wherein R1, R2,R3 are defined in the description.

Description

technical field [0001] The invention relates to a class of hydroxyanthraquinone derivatives and their use in the preparation of medicines for treating cancer. technical background [0002] Cancer is one of the most dangerous diseases to human health and quality of life. Finding anticancer drugs with high efficiency, high selectivity and small side effects is the main direction of anticancer drug development. [0003] Hydroxyanthraquinone compounds contained in various Chinese herbal medicines have been found to have certain anti-tumor activity, mainly inhibiting the DNA synthesis of cancer cells. For example, it has inhibitory effect on the growth of human proleukocyte (HL-60), mouse sarcoma, mouse liver tumor and other tumor strains, [Edited by Huang Taikang, Commonly Used Chinese Herbal Medicine Components and Pharmacological Handbook, P1225, 1994, China Medical Science and Technology Publishing Society]. However, because the antitumor activity of natural hydroxyanthraqu...

Claims

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Application Information

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IPC IPC(8): A61K9/08A61K9/10A61K9/20A61K9/48A61K31/122A61P35/00C07C50/34
Inventor 古练权陆豫符立梧邓焯安黄志纾马林徐忠宪陈新滋
Owner SUN YAT SEN UNIV
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