6-(azacyclo-substitute) anthraquinone platinous chloride complex as well as preparation method and application thereof

A technology of anthraquinone platinum dichloride and nitrogen heterocycle, which is applied in the field of medicine, can solve the problems of poor targeting, high toxicity, and single biological activity, and achieve good anti-tumor activity and safety effects

Active Publication Date: 2014-02-05
LIAONING UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] 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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  • 6-(azacyclo-substitute) anthraquinone platinous chloride complex as well as preparation method and application thereof
  • 6-(azacyclo-substitute) anthraquinone platinous chloride complex as well as preparation method and application thereof
  • 6-(azacyclo-substitute) anthraquinone platinous chloride complex as well as 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] Compound 1

[0023] 1. Synthesis of 6-methyl-1,4-dihydroxyanthraquinone

[0024]

[0025] 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%).

[0026] 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);

[0027] 2. Synthesis of 6-methyl-1,4-bis(methoxymethyl ether)-anthraquinone

[0028]

[0029] Under nitrogen protection conditions at 0°C, 6-methyl-1,4-dihydroxya...

Embodiment 2

[0052] Example 2: Bis-6-[(3-aminopyridine)methyl]-1,4-dihydroxyanthraquinone platinum dichloride complex (compound 2)

[0053]

[0054] Compound 2

[0055] 1. Synthesis of 6-[(3-aminopyridine)methyl]-1,4-bis(methoxymethyl ether)anthraquinone

[0056]

[0057] Under nitrogen protection, 5.06 g (12 mmol) of 6-bromomethyl-1,4-bis(methoxymethyl ether)-anthraquinone, 1.32 g (12 mmol) of 3-aminopyridine were added to a 500 ml eggplant-shaped bottle. mol), 3.31 grams of potassium carbonate (24 mmol), 300 milliliters of acetone solvent, after reflux and stirring 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. (83% yield).

[0058] MS:435m / z(M+H).

[0059] 1 H-NMR (DMSO-d 6 ):δ8.28(d,J=8.2Hz,1H),8.21(s,1H),7.81(dd,J=1.2,J=4.0Hz,1H),7....

Embodiment 3

[0065] Example 3: Bis-6-[(1-methyl-5-mercapto)methyl]-1,4-dihydroxyanthraquinone platinum dichloride complex (compound 3)

[0066]

[0067] Compound 3

[0068] 1. Synthesis of 6-[(1-methyl-5-mercapto)methyl]-1,4-bis(methoxymethyl ether)anthraquinone

[0069]

[0070] Under nitrogen protection, add 5.06 g (12 mmol) of 6-bromomethyl-1,4-bis(methoxymethyl ether)-anthraquinone, 1-methyl-5-mercapto-tetra 1.74 g (15 mmol) of oxazole, 0.6 g of sodium hydroxide (15 mmol), 100 ml of N,N-dimethylformamide solvent, stirred at 60°C for 3 hours, then mixed with 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%).

[0071] MS:457m / z(M+H).

[0072] 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);

[0073] 2. Synthesis of...

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Abstract

The invention discloses a 6-(azacyclo-substitute) anthraquinone platinous chloride complex as well as a preparation method and an application thereof. The 6-(azacyclo-substitute) anthraquinone platinous chloride complex disclosed by the invention has the structure of a formula I. The complex disclosed by the invention has good anti-tumor activity and security, and has great application values in treating lung cancer, liver cancer, leukemia, colon cancer and ovarian cancer in the medicine field.

Description

technical field [0001] 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 [0002] Anthraquinones are broad-spectrum anti-tumor drugs developed in the 1970s, among which doxorubicin (ADR), daunorubicin (DNR) and mitoxantrone (IDA) are their representative drugs, which are effective for the treatment of breast cancer. 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 mitoxantrone is 5 times that of doxorubicin, and because it has no amino sugar structure, it has low cardiotoxicity, and has a better therapeutic effect on non-Hodgkin's disease lymphoma, leukemia, advanced breast cancer and other tumors. it ...

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 王晓芳王洋韩爽陈烨刘举周云鹏张秋实徐小剑赵楠
Owner LIAONING UNIVERSITY
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