Sulfonyl piperazine containing coumarin pyrazole compounds, preparation of coumarin pyrazole compounds and application of coumarin pyrazole compounds in tumor cell inhibition

A technology containing sulfonylpiperazine and coumarin, which can be used in antineoplastic drugs, drug combinations, organic chemistry, etc., and can solve problems such as cytotoxicity

Inactive Publication Date: 2015-11-18
NANJING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

And Manojkumar et al also reported that some synthetic heterocyclic coumarin compounds have cytotoxic effect on DLA and EAC cells

Method used

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  • Sulfonyl piperazine containing coumarin pyrazole compounds, preparation of coumarin pyrazole compounds and application of coumarin pyrazole compounds in tumor cell inhibition
  • Sulfonyl piperazine containing coumarin pyrazole compounds, preparation of coumarin pyrazole compounds and application of coumarin pyrazole compounds in tumor cell inhibition
  • Sulfonyl piperazine containing coumarin pyrazole compounds, preparation of coumarin pyrazole compounds and application of coumarin pyrazole compounds in tumor cell inhibition

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] Example 1: Preparation of 2-((4-(benzenesulfonyl)piperazin-1-yl)methyl)chromeno[4,3-c]pyrazol-4(2H)-one (Compound 1)

[0018]

[0019] 0.06 mmol of 4-hydroxycoumarin was dissolved in 46.2 ml of anhydrous N,N-dimethylformamide, and the reaction liquid was cooled to below 0°C. Under the condition below 0°C, slowly add POCl dropwise while stirring 3 0.18mmol, to POCl 3 After the addition was complete, the reaction solution was slowly warmed up to room temperature and stirred for 0.5 h, then heated up to 65-70° C. and stirred for 6 h. The reaction was tracked and monitored by TLC. After the reaction was completed, the reaction solution was poured into 200 g of ice-water mixture and stirred vigorously, and a large amount of light yellow solid 1 was precipitated. The solid was suction filtered and washed with 5% Na 2 CO 3 The aqueous solution was washed, and the obtained solid was dried to obtain the intermediate.

[0020] Dissolve 1 mmol of the solid obtained in step...

Embodiment 2

[0023] Example 2: Preparation of 2-((4-tosylpiperazin-1-yl)methyl)chromeno[4,3-c]pyrazol-4(2H)-one (Compound 2)

[0024]

[0025] The preparation method is the same as in Example 1. The product is a white powdery solid. Yield 57%. Mp: 176-177°C. 1 HNMR (400MHz, CDCl 3 ): 8.20(s, 1H, ArH), 8.05(d, J=7.72Hz, 1H, ArH), 7.61(d, J=7.92Hz, 2H, ArH), 7.49(t, J=7.70Hz, 1H, ArH), 7.38(d, J=8.28Hz, 1H, ArH), 7.31(t, J=9.66Hz, 3H, ArH), 5.04(s, 2H, -CH 2 ), 3.05(s, 4H, -CH 2 CH 2 ), 2.75(t, J=4.38Hz, 4H, -CH 2 CH 2 ), 2.40 (s, 3H, CH 3 ).MS (ESI): 439.32 (C 22 h 23 N 4 o 4 S, [M+H] + ).Anal.CalcdforC 22 h 22 N 4 o 4S: C, 60.26; H, 5.06; N, 12.78%. Found: C, 60.27; H, 5.08; N, 12.76%.

Embodiment 3

[0026] Example 3: 2-((4-((4-methoxyphenyl)sulfonyl)piperazin-1-yl)methyl)chromeno[4,3-c]pyrazole-4(2H) - Preparation of ketone (compound 3)

[0027]

[0028] The preparation method is the same as in Example 1. The product is a white powdery solid. Yield 54%. Mp: 182-184°C. 1 HNMR (400MHz, CDCl 3 ): 8.20(s, 1H, ArH), 8.05(d, J=7.64Hz, 1H, ArH), 7.66(d, J=8.36Hz, 2H, ArH), 7.48(t, J=5.76Hz, 1H, ArH), 7.38(d, J=8.24Hz, 1H, ArH), 7.32(t, J=7.52Hz, 1H, ArH), 6.96(d, J=8.52Hz, 2H, ArH), 5.05(s, 2H ,-CH 2 ), 3.85(s, 3H, OCH 3 ), 3.05(s, 4H, -CH 2 CH 2 ), 2.74 (d, J=4.32Hz, 4H, -CH 2 CH2). MS (ESI): 455.37 (C 22 h 23 N 4 o 5 S, [M+H] + ).Anal.CalcdforC 22 h 22 N 4 o 5 S: C, 58.14; H, 4.88; N, 12.33%. Found: C, 58.15; H, 4.91; N, 4.86%.

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Abstract

The invention provides sulfonyl piperazine containing coumarin pyrazole compounds. The compounds have a general formula shown in the specification, wherein R is shown in the specification. Experiments prove that the sulfonyl piperazine containing coumarin pyrazole compounds have different levels of inhibiting effects on human colon carcinoma cell lines HCT-116, human lung cancer cell lines A549, liver cancer cells Huh7 and human spinal cord leukemia M3 cell lines HL60, so that the compounds can be possibly used for preparing anti-cancer drugs. The invention discloses a preparation method of the sulfonyl piperazine containing coumarin pyrazole compounds.

Description

technical field [0001] The invention relates to a coumarinopyrazole compound containing sulfonyl piperazine and its preparation and application in inhibiting tumor cells. Background technique [0002] Natural and synthetic coumarins possess various biological activities and are known as anticoagulant and antithrombotic agents. Some derivatives have been reported to have photosensitizing, anti-HIV, lipid-lowering, anti-inflammatory, anti-tumor and anti-oxidative effects, and can inhibit lipid peroxidation, scavenge free radicals, relax blood vessels, and regulate cardiovascular function. Studies have found that many coumarin compounds have cytotoxic effects on mammalian cancer cell lines. Recently, a series of aryl sulfonylurea coumarins have been reported to effectively inhibit the proliferation of various tumor cells at low concentrations. And Manojkumar et al also reported that some synthetic heterocyclic coumarin compounds have cytotoxic effect on DLA and EAC cells. Ar...

Claims

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Application Information

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IPC IPC(8): C07D491/052A61P35/00A61P35/02
CPCC07D491/052
Inventor 朱海亮吴逊殷勇王雪沙少
Owner NANJING UNIV
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