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Mono6-(azabicyclo-substitution) anthraquinone platinous chloride compound and preparation method and application thereof

An anthraquinone platinum dichloride, nitrogen heterocycle technology, applied in the field of medicine, can solve the problems of poor targeting, single biological activity, high toxicity, etc., and achieve the effect of good anti-tumor activity and safety

Active Publication Date: 2016-01-20
LIAONING UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] However, anthraquinones and platinum compounds still have many shortcomings and deficiencies as antitumor drugs, and they are highly toxic, such as bone marrow toxicity, nephrotoxicity, and cardiotoxicity.
Poor targeting, single biological activity, etc.

Method used

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  • Mono6-(azabicyclo-substitution) anthraquinone platinous chloride compound and preparation method and application thereof
  • Mono6-(azabicyclo-substitution) anthraquinone platinous chloride compound and preparation method and application thereof
  • Mono6-(azabicyclo-substitution) anthraquinone platinous chloride compound and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Example 1: Bis[6-tetrazolium-1,4-dihydroxy)-anthraquinone] platinum dichloride complex (compound 1)

[0021]

[0022] 1. Synthesis of 6-methyl-1,4-dihydroxyanthraquinone

[0023]

[0024] Under nitrogen protection conditions, add 5.00 g (31 mmol) 4-methylphthalic anhydride, 3.74 g (34 mmol) hydroquinone and 15.0 g (0.11 mol) aluminum trichloride. The mixture was stirred at 220°C for 2 hours, cooled to 25°C, then poured into 300 ml of ice water, acidified with 12N hydrochloric acid, the precipitated solid was filtered, washed with water, and dried in vacuo to obtain the product 6-methyl-1,4 - Dihydroxyanthraquinone 6.28 g (yield: 80%).

[0025] MS:255m / z(M+H). 1 H-NMR (DMSO-d 6 ): δ12.94(s,1H),12.90(s,1H),8.22(d,J=8Hz,1H),8.12(s,1H),7.63(d,J=8Hz,1H),7.29(s ,2H),2.55(s,3H);

[0026] 2, Synthesis of 6-methyl-1,4-bis(methoxymethyl ether group)-anthraquinone

[0027]

[0028] Under nitrogen protection conditions at 0°C, 6-methyl-1,4-dihydroxyanthraquinone (20...

Embodiment 2

[0051] Example 2: Two 6-[(3-aminopyridine) methyl]-1,4-dihydroxyanthraquinone platinum dichloride complex (compound 2)

[0052]

[0053] 1, Synthesis of 6-[(3-aminopyridine)methyl]-1,4-bis(methoxymethyl ether group)anthraquinone

[0054]

[0055] Under the protection of nitrogen, 5.06 grams (12 mmoles) of 6-bromomethyl-1,4-bis(methoxymethyl ether group)-anthraquinone, 1.32 grams (12 mmoles) of 3-aminopyridine were added to a 500 ml eggplant-type bottle mol), 3.31 grams of potassium carbonate (24 mmoles), 300 milliliters of acetone solvent, after reflux stirring reaction for 4 hours, the solution was spin-dried, extracted with 100 milliliters of ethyl acetate and 100 milliliters of water, separated the ethyl acetate phase and then subtracted Concentrated under reduced pressure, and the crude product was separated by column to obtain 4.35 g of the product. (Yield 83%).

[0056] MS:435m / z(M+H).

[0057] 1 H-NMR (DMSO-d 6 ): δ8.28(d, J=8.2Hz, 1H), 8.21(s, 1H), 7.81(dd, ...

Embodiment 3

[0063] Example 3: Two 6-[(1-methyl-5 mercapto) methyl]-1,4-dihydroxyanthraquinone platinum dichloride complex (compound 3)

[0064]

[0065] 1, Synthesis of 6-[(1-methyl-5 mercapto) methyl]-1,4-bis(methoxymethyl ether group)anthraquinone

[0066]

[0067] Under nitrogen protection, 5.06 grams (12 mmoles) of 6-bromomethyl-1,4-bis(methoxymethyl ether)-anthraquinone, 1-methyl-5 mercapto-tetra 1.74 g (15 mmol) of nitrogen azole, 0.6 g of sodium hydroxide (15 mmol), 100 ml of N,N-dimethylformamide solvent, stirred at 60°C for 3 hours, and then used 100 ml of ethyl acetate, 100 Extract with milliliter of water, separate the ethyl acetate phase and concentrate under reduced pressure. The crude product is recrystallized from hot acetone to obtain 5.02 g of the product. (Yield 91%).

[0068] MS:457m / z(M+H).

[0069] 1 H-NMR (DMSO-d 6 ):δ8.16(d,J=8.0Hz,1H),8.10(s,1H),7.77(d,J=8.2Hz,1H),7.42(s,2H),6.24(s,4H),4.15 (s,2H),3.57(s,6H),2.63(s,3H);

[0070] 2. Synthesis of double ...

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Abstract

The invention discloses a mono6-(azabicyclo-substitution) anthraquinone platinous chloride compound and a preparation method and application thereof. The mono6-(azabicyclo-substitution) anthraquinone platinous chloride compound is of a structure shown in the formula II. The obtained compound has the better anti-tumor activity and safety and has the quite good application value in the field of medicine for treating the lung cancer, the liver cancer, the leukemia, the colon cancer and the ovarian cancer.

Description

[0001] This application is a divisional application with a filing date of November 19, 2013, an application number of 201310589727.3, and an invention title of "6-(nitrogen-heterocyclic substituted) anthraquinone platinum dichloride complex and its preparation method and application". technical field [0002] The invention belongs to the field of medicine, and in particular relates to a 6-(nitroheterocycle substituted) anthraquinone platinum dichloride complex capable of inhibiting tumor cell growth and having antitumor effects, and a preparation method and application thereof. Background technique [0003] Anthraquinones are broad-spectrum antineoplastic drugs developed in the 1970s, among which doxorubicin (ADR), daunorubicin (DNR) and mitoxantrone (IDA) are their representative drugs. Cancer and other solid tumors and acute non-lymphocytic leukemia have good results, and are still commonly used anti-tumor drugs on the market. Among them, the anticancer activity of mitoxan...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00A61K31/555A61P35/00A61P35/02
CPCA61K31/555C07F15/0093C09B1/02C09B1/14C09B1/515
Inventor 王晓芳王洋陈烨刘举周云鹏张秋实韩爽
Owner LIAONING UNIVERSITY
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