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2-(4-bromophenyl) quinoline-4-formic acid complex and preparation method and application thereof

A bromophenyl complex technology, applied in the field of 2-(4-bromophenyl) quinoline-4-carboxylic acid complex and its preparation and application, can solve the problems of strong irritation, high toxicity, difficult absorption, etc. , to achieve good stability, improved antibacterial performance, and easy purification

Inactive Publication Date: 2014-05-21
SHANDONG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Many metal ions with therapeutic effects cannot be directly used in clinical practice due to their high toxicity, strong irritation, and difficulty in absorption. However, their toxicity and irritation can be reduced if they are converted into complexes.

Method used

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  • 2-(4-bromophenyl) quinoline-4-formic acid complex and preparation method and application thereof
  • 2-(4-bromophenyl) quinoline-4-formic acid complex and preparation method and application thereof
  • 2-(4-bromophenyl) quinoline-4-formic acid complex and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] 2-(4-Bromophenyl)quinoline-4-carboxylic acid manganese(Ⅱ)

[0032] (1) Dissolve isatin (1.18g, 8.00mmol), 4-bromoacetophenone (0.40g, 2.00mmol), potassium hydroxide (2.24g, 40.00mmol) in a mixed solution of 2mL ethanol and 18mL water, Heat to reflux for 12 hours, after cooling, pour the reaction solution into 20mL of water, adjust the pH of the system to 4 with 1M hydrochloric acid, filter the resulting precipitate, wash with water to obtain a yellow solid 2-(4-bromophenyl)quinoline-4-carboxylic acid 597mg, yield: 91%;

[0033] Detect 2-(4-bromophenyl) quinoline-4-carboxylic acid to get IR(KBr, cm -1 ):3445,2361,1714,1588,1544,1490,1403,1367,1227,1197,1075,1007,831,802,766,713,541,514. 1 H NMR(500MHz,DMSO,δ):8.65(d,J=8.0Hz,1H),8.46(s,1H),8.27(d,J=8.5Hz,2H),8.17(d,J=8.0Hz, 1H),7.87(t,1H),7.77(d,J=8.5Hz,2H),7.21(t,1H).Anal.Calcd for C 16 h 10 BrNO 2:C,58.56;H,3.07;N,4.27.Found:C,58.67;H,3.04;N,4.29%;

[0034] (2) Dissolve 2-(4-bromophenyl)quinoline-4-carboxylic aci...

Embodiment 2

[0039] 2-(4-Bromophenyl)quinoline-4-carboxylate cobalt(Ⅱ)

[0040] Step (1) is the same as step (1) in Example 1;

[0041] Step (2) Dissolve 2-(4-bromophenyl)quinoline-4-carboxylic acid (13.1mg, 0.04mmol) in 6mL of methanol, add cobalt acetate (10.0mg, 0.04mmol) in 4mL of methanol solution, Stir at room temperature for 4 minutes, filter, and stand for 4 days, 6.0-8.0 mg of yellow crystals appear, filter, wash with methanol three times, and dry in an anhydrous calcium chloride desiccator to obtain the product. Yield 45%.

[0042] The result of elemental analysis of the product: Calculated value: C(%), 52.53; H(%), 3.37; N(%), 3.60;

[0043] Measured value: C(%), 52.69; H(%), 3.35; N(%), 3.62

[0044] IR(KBr,cm -1 ):3446,3065,2361,1645,1603,1536,1464,1404,1367,1032,810,759,666,468.

Embodiment 3

[0046] 2-(4-Bromophenyl)quinoline-4-carboxylate zinc(Ⅱ)

[0047] Step (1) is the same as step (1) in Example 1;

[0048] Step (2) 2-(4-bromophenyl)quinoline-4-carboxylic acid (13.1mg, 0.04mmol) was dissolved in 8mL of methanol, and added to a solution of zinc acetate (8.8mg, 0.04mmol) in 4mL of methanol, Stir at room temperature for 3 minutes, filter, and stand for 3 days, 11.0-12.0 mg of yellow crystals appear, filter, wash with methanol three times, and dry in an anhydrous calcium chloride desiccator to obtain the product. Yield 72%.

[0049] The result of elemental analysis of the product: Calculated value: C(%), 52.10; H(%), 3.34; N(%), 3.57;

[0050] Measured value: C(%), 52.31; H(%), 3.32; N(%), 3.58;

[0051] IR(KBr,cm -1 ):3445,3063,2361,1651,1588,1547,1403,1321,1106,1073,1029,810,761,665,469.

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Abstract

The invention relates to a 2-(4-bromophenyl) quinoline-4-formic acid complex and a preparation method and application thereof. The structural formula of the complex is shown in the specification, wherein M is metal and can be Mn, Co, Cd or Zn. The 2-(4-bromophenyl) quinoline-4-formic acid complex can be used for preparing antibacterial agents, is simple in synthesis, convenient to purify, high in yield and high in stability in air. In comparison with the ligand, the antibacterial property of the complex can be remarkably improved, and the metal ion has the regulating effect in the antibacterial activity.

Description

technical field [0001] The invention relates to a 2-(4-bromophenyl)quinoline-4-carboxylic acid complex and its preparation method and application. Background technique [0002] Due to their unique physical and chemical properties, organometallic coordination compounds have important application value in the fields of nonlinear optics, molecular magnets, molecular switches, gas storage and separation, etc. Many metal ions with therapeutic effects cannot be directly used clinically due to their high toxicity, strong irritation, and difficulty in absorption. However, their toxicity and irritation can be reduced if they are converted into complexes. In 1965, Rosenberg discovered that cisplatin (cis-dichlorodiammine platinum) could effectively inhibit the cell division of Escherichia coli, and then confirmed its anticancer activity. In 1971, he first verified the effect of cisplatin on cancer cells in clinical trials. Therefore, drug complexes have become a hot field in the desi...

Claims

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Application Information

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IPC IPC(8): C07F13/00C07F15/06C07F3/06C07F3/08A61K31/555A61P31/04
Inventor 秦洁类娜朱海亮孙娟李季王忻怡
Owner SHANDONG UNIV OF TECH
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