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3,4-disubstituted pyrrole compound as well as preparation method and application thereof

A disubstituted pyrrole and compound technology, applied in 3 fields, can solve problems such as toxic and side effects, affecting normal dividing cells, etc.

Active Publication Date: 2014-09-03
SHANGHAI JIAO TONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Due to the specific mechanism of action of anti-tumor compounds, these compounds usually seriously affect normal dividing cells while killing tumor cells, causing varying degrees of toxic and side effects

Method used

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  • 3,4-disubstituted pyrrole compound as well as preparation method and application thereof
  • 3,4-disubstituted pyrrole compound as well as preparation method and application thereof
  • 3,4-disubstituted pyrrole compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055] Synthesis of (4-(3,4-Difluorophenyl)-1H-pyrrol-3-yl)(2-fluorophenyl)methanone:

[0056] Dissolve 1-(2-fluorophenyl)-3-(3,4-difluorophenyl)propenone (0.26g, 1.0mmol) and TosMIC (0.21g, 1.1mmol) in 10mL of dry THF or DMSO After stirring and cooling in an ice bath, t-BuOK (0.14g, 1.2mmol) was added slowly or in batches. After the reactants were fully stirred and contacted, they could react at room temperature. The reaction was stopped after 2h. The excess t-BuOK was quenched with ice-saturated aqueous ammonium chloride solution. The reaction solution was extracted three times with ethyl acetate (75mL, 25mL×3). The organic layers were combined and washed once with saturated brine. Sodium sulfate is allowed to stand to dry. The solvent was evaporated under reduced pressure, and silica gel column chromatography (petroleum ether: ethyl acetate = 1:2) gave white (4-(3,4-difluorophenyl)-1H-pyrrol-3-yl)(phenyl) ) Methyl ketone solid (0.19 g, 0.64 mmol), yield 69.4%.

[0057] The ex...

Embodiment 2

[0060] Synthesis of (4-(3,4-Difluorophenyl)-1H-pyrrol-3-yl)(4-fluorophenyl)methanone

[0061] The preparation method is the same as that of Example 1, and the raw materials are 1-(4-fluorophenyl)-3-(3,4-difluorophenyl)propenone and TosMIC.

[0062] The product is a yellowish solid with a yield of 83.7%.

[0063] The experimental data of the product is as follows:

[0064] 1H NMR (400MHz, DMSO) δ (ppm): 11.77 (s, 1H, NH), 7.76 (dd, J1 = 6.0 Hz, J2 = 8.4 Hz, 2H, -CO-Ar-H), 7.48 (ddd, J1 =1.6Hz, J2=8.0Hz, J3=12Hz, 1H, Ar-H), 7.36-7.26 (m, 4H, Ar-H+-CO-Ar-H+pyrrole-H), 7.25-7.20 (m, 1H) , Ar-H), 7.19 (s, 1H, pyrrole-H); 13C NMR (100MHz, DMSO-d6) δ (ppm): 188.79, 165.29, 162.81, 150.08, 149.95, 149.10, 148.97, 147.66, 147.54, 146.68 , 146.55, 136.41, 132.77, 131.66, 131.57, 128.57, 124.86, 123.30, 120.41, 120.22, 117.12, 116.94, 116.64, 116.48, 115.19, 114.98.

Embodiment 3

[0066] Synthesis of (4-(3,4-Difluorophenyl)-1H-pyrrol-3-yl)(2-chlorophenyl)methanone

[0067] The preparation method is the same as in Example 1. The raw materials are 1-(2-chlorophenyl)-3-(3,4-difluorophenyl)propenone and TosMIC.

[0068] The product is a yellowish solid with a yield of 76.2%.

[0069] The experimental data of the product is as follows:

[0070] 1H NMR (400MHz, DMSO) δ (ppm): 11.81 (s, 1H, NH), 7.59 (dd, J1 = 8.0 Hz, J2 = 12.8 Hz, 1H, -CO-Ar-H), 7.53-7.44 (m , 3H, -CO-Ar-H), 7.42 (d, J=6.8 Hz, 1H, Ar-H), 7.39-7.33 (m, 2H, Ar-H), 7.16 (s, 1H, pyrrole-H) , 7.02 (s, 1H, pyrrole-H); 13CNMR (100MHz, DMSO-d6) δ (ppm): 188.48, 149.98, 149.85, 149.30, 149.18, 147.56, 147.43, 146.88, 146.75, 140.52, 132.43, 130.77, 130.59 , 129.53, 128.57, 126.80, 125.17, 122.92, 121.30, 120.89, 117.43, 117.25, 116.59, 116.42.

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Abstract

The invention discloses a 3,4-disubstituted pyrrole compound. The compound has the following structure shown in a general formula in the specification. A preparation method of the 3,4-disubstituted pyrrole compound comprises a step of performing Michael addition, cyclization and elimination reaction on disubstituted olefin and p-toluenesulfonyl isocyanide. Compared with the prior art, a series of 3,4-disubstituted pyrrole compounds disclosed by the invention have high antitumor activity in vitro; meanwhile, the proliferation inhibition activity to normal cells is inhibited weakly, the excellent tumor cell selectivity is displayed, and the 3,4-disubstituted pyrrole compound can be used as a kind of safe and effective antitumor drugs in the future. The preparation method is convenient to carry out, short in reaction period and high in yield.

Description

Technical field [0001] The present invention relates to organic compounds, in particular to a 3,4-disubstituted pyrrole compound and its preparation method and application. Background technique [0002] Tumors are abnormal lesions formed by the body under the action of various carcinogenic factors, and the cells of local tissues lose their normal regulation of their growth at the gene level, leading to their clonal abnormal proliferation. According to the "2012 China Cancer Registry Annual Report", there are about 3.12 million new cancer cases in the country every year, and an average of 8550 new cancers occur every day, and the cancer incidence rate is as high as 28.5591 per 100,000. Although researchers from various countries have made great progress in tumor research and treatment, tumors are still one of the main causes of human death. In the current medical system, cancer treatment often uses chemotherapy alone or combined with surgical treatment and radiotherapy. The huge ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D207/333C07D401/06C07D409/06C07D207/42C07D207/34C07D207/335C07D401/04C07D409/14A61P35/00A61P35/02
CPCC07D207/333C07D207/335C07D207/34C07D207/42C07D401/04C07D401/06C07D409/06C07D409/14
Inventor 毛振民兰岚覃维曦詹晓平刘增路隆艳
Owner SHANGHAI JIAO TONG UNIV
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