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2'-pyrazol-1H-imidazole [4,5-f][1,10] phenanthroline derivate and preparing method and application thereof

A technology of derivatives and imidazoles, applied in the field of 2′-pyrazole-1H-imidazol[4,5-f][1,10]phenanthroline derivatives and their preparation and application, can solve the problem of no compound and synthesis and application issues, to achieve the effects of low equipment requirements, high yield and purity, and simple preparation methods

Active Publication Date: 2017-04-19
ZHEJIANG UNIV OF TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

So far, there is no report of compound and synthesis and application in the present invention

Method used

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  • 2'-pyrazol-1H-imidazole [4,5-f][1,10] phenanthroline derivate and preparing method and application thereof
  • 2'-pyrazol-1H-imidazole [4,5-f][1,10] phenanthroline derivate and preparing method and application thereof
  • 2'-pyrazol-1H-imidazole [4,5-f][1,10] phenanthroline derivate and preparing method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Example 1.2-(1-benzyl-3-(4-bromophenyl)-1H-pyrazol-4-yl)-1H-imidazo[4,5-f][1,10]phenanthroline (12c ) preparation

[0043] (1) 12c chemical structural formula:

[0044]

[0045] (2) Chemical reaction steps:

[0046]

[0047] The first step reaction: dissolve p-bromoacetophenone (1.99g, 10.0mmol) in 25mL of absolute ethanol, add semicarbazide hydrochloride (1.23g, 11.0mmol) and anhydrous sodium acetate (0.90g, 11.0mmol), React at 75°C for 6 hours, concentrate, cool, precipitate a white solid, filter, recrystallize with ethanol / water (4:1), filter, wash with a small amount of water, and dry to obtain 2.30-2.36g of white solid 2c, yield 89.8 ~92.0%.

[0048] The second step reaction: 15.5mL DMF was stirred for 10 minutes in an ice bath, 3.1mL of phosphorus oxychloride was slowly added dropwise to it, keeping the temperature below 5°C, stirred for 15 minutes, and compound 2c (2.0g, 7.8mmol), then slowly warming up to 65 ° C, TLC detection, until the reaction is co...

Embodiment 2

[0052] Example 2. Preparation of 2-(3-(4-fluorophenyl)-1H-pyrazol-4-yl)-1H-imidazol[4,5-f][1,10]phenanthroline (10a)

[0053] (1) 10a chemical structural formula:

[0054]

[0055] (2) Chemical reaction steps:

[0056] Test method and step are with embodiment 1 (save the 3rd step reaction). After purification, the pure product (10a) was obtained as a yellow solid, with a yield of 78.8-80.9%; m.p.272-274°C, purity: 96.6% (HPLC). 1 H NMR (DMSO-d 6 ,500MHz,ppm):δ13.534(br.s,2H,NH),9.041-9.029(dd,J 1 =4.5Hz,J 2 =2.0Hz,2H,Phenanthroline-H),8.837-8.822(d,J 1 =7.5Hz,2H,Phenanthroline-H),8.380(br.s,1H,CH),8.096-8.068(dd,J 1 =8.0Hz,J 2 =6.0Hz,2H,Ph-H),7.853-7.828(dd,J 1 =8.0Hz,J 2 =4.5Hz,2H,Phenanthroline-H),7.312(br.s,2H,Ph-H).MS(ESI)calcd for C 22 h 13 FN 6 :380.12,found:381.1(M+H + ).

Embodiment 3

[0057] Example 3. Preparation of 2-(3-(4-chlorophenyl)-1H-pyrazol-4-yl)-1H-imidazol[4,5-f][1,10]phenanthroline (10b)

[0058] (1) 10b chemical structural formula:

[0059]

[0060] (2) Chemical reaction steps:

[0061] Test method and step are with embodiment 1 (save the 3rd step reaction). After purification, the pure product (10b) was obtained as a yellow solid, with a yield of 81.2-83.5%; m.p.285-287°C, purity: 95.8% (HPLC). 1 H NMR (DMSO-d 6 ,500MHz,ppm):δ13.551-13.531(d,J 1 =10Hz,2H,NH),9.039-9.027(dd,J 1 =4.0Hz,J 2 =1.5Hz,2H,Phenanthroline-H),8.824(br.s,2H,Phenanthroline-H),8.486(br.s,1H,CH),8.067(br.s,2H,Ph-H),7.830( br.s,2H,Phenanthroline-H),7.622(br.s,1H,Ph-H),7.493-7.481(d,J 1 =6.0Hz,1H,Ph-H).MS(ESI)calcd for C 22 h 13 ClN 6 :396.09,found:397.1(M+H + ).

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Abstract

The invention relates to a 2'-pyrazol-1H-imidazole [4,5-f][1,10] phenanthroline derivate and a preparing method and application thereof. According to the 2'-pyrazol-1H-imidazole[4,5-f][1,10] phenanthroline derivate, different substituted acetophenone and semicarbazlde hydrochloride and 2,4-dinitrobenzene serve as raw materials, the target compound, namely the 2'-pyrazol-1H-imidazole [4,5-f][1,10] phenanthroline derivate is obtained through a five-step reaction, and the obtained target compound is used for applied research of cell line growth inhibition and apoptosis activity for resisting three kinds of cancer cells including the non-small cell lung cancer cell lines A549, human liver cancer cell lines HepG2 and human breast carcinoma cell lines MCF-5. Most compounds can make the experiment cancer cells restrained and apoptotic, high effects are generated on the A549 and HepG2 cell lines are achieved particularly, and selective toxicity on the A549 cell lines is generated particularly. According to the 2'-pyrazol-1H-imidazole [4,5-f][1,10] phenanthroline derivate, a large reference value is provided for finding new anti-tumor micromolecular medicines and is particularly provided for promoting clinical medicine research and development of the phenanthroline derivate.

Description

technical field [0001] The invention relates to a preparation method of 2'-pyrazole-1H-imidazol[4,5-f][1,10]phenanthroline derivatives and an application in the development of antitumor drugs. Background technique [0002] Cancer is a high-profile public health problem causing incalculable losses, with lung cancer being the most common and fatal cancer. In the male group, the incidence of lung cancer accounts for 17% of the new cancer cases in the world, and the death cases account for about a quarter of the global cancer deaths. Liver cancer is also the top five in the incidence and mortality of malignant tumors in the male group Diseases: For women, among malignant tumors, the incidence of breast cancer ranks first, while the mortality rate ranks the top three. Among lung cancer cases, 85% of patients belong to non-small cell lung cancer, and only 15% of patients belong to small cell lung cancer, and most cancer patients are resistant to clinical drugs. Lung cancer has a...

Claims

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Application Information

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IPC IPC(8): C07D471/14A61P35/00
CPCC07D471/14
Inventor 张文刘佳春成梅
Owner ZHEJIANG UNIV OF TECH
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