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Pyrimidine phenylurea anti-tumor compound and preparation method and application thereof

A pyrimidine phenylurea and anti-tumor technology, which is applied in the field of medicine, can solve problems such as unseen reports, achieve the effects of reducing the possibility of drug resistance, simplifying the synthesis steps, and improving the anti-tumor effect

Inactive Publication Date: 2018-11-13
中国医科大学
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Based on the structural characteristics of the designed pyrimidine hydrazine anti-tumor compounds, the applicant introduced a new group - urea structure to replace the bisacyl hydrazine structure, in order to obtain a new compound with more anti-tumor effect. No relevant structure has been seen. to report

Method used

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  • Pyrimidine phenylurea anti-tumor compound and preparation method and application thereof
  • Pyrimidine phenylurea anti-tumor compound and preparation method and application thereof
  • Pyrimidine phenylurea anti-tumor compound and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0054] Preparation of N'-(2-methylphenyl)-3-(uracil-5-sulfonamido)phenylurea A1.

[0055] a. Preparation of uracil-5-sulfonyl chloride: at 25-40°C, add uracil (5g, 44.63mmoL) and thionyl chloride (15ml, 89.26mmoL) into a 100mL reaction flask, activate 1.5-3 Add chlorosulfonic acid (25g, 133.89mmoL) to react at 50-65°C for 4-5h, and continue to react at 70-90°C for 5-8h; add the reaction solution into ice water, precipitate out, suction filter, wash with water for 50 C and dried to obtain 4.50 g of white solid, yield: 70%.

[0056] b. Dissolve 3-nitrobenzohydrazide (5.00g, 27.60mmol) in dichloromethane in a 100mL reaction flask at 0°C, and then add sodium nitrite (3.81g, 55.20mmol) aqueous solution Diluted hydrochloric acid (2.01g, 55.20mmol) was added dropwise, reacted for about 1-2 hours, separated and dried at 50°C to obtain 3-nitrobenzoyl azide yellow solid (5.00g, 26.05mmol), yield 94.28%.

[0057] c.: Dissolve 3-nitrobenzoyl azide (5.00g, 26.05mmol) in carbon tetrachlor...

Embodiment 2

[0062] Preparation of N'-(3-methylphenyl)-3-(uracil-5-sulfonamido)phenylurea A2

[0063] a. Preparation of uracil-5-sulfonyl chloride: at 25-40°C, add uracil (5g, 44.63mmoL) and thionyl chloride (15ml, 89.26mmoL) into a 100mL reaction flask, activate 1.5-3 Add chlorosulfonic acid (25g, 133.89mmoL) to react at 50-65°C for 4-5h, and continue to react at 70-90°C for 5-8h; add the reaction solution into ice water, precipitate out, suction filter, wash with water for 50 C and dried to obtain 4.50 g of white solid, yield: 70%.

[0064] b. Dissolve 3-nitrobenzohydrazide (5.00g, 27.60mmol) in dichloromethane in a 100mL reaction flask at 0°C, and then add sodium nitrite (3.81g, 55.20mmol) aqueous solution Diluted hydrochloric acid (2.01g, 55.20mmol) was added dropwise, reacted for about 1-2 hours, separated and dried at 50°C to obtain 3-nitrobenzoyl azide yellow solid (5.00g, 26.05mmol), yield 94.28%.

[0065] c.: Dissolve 3-nitrobenzoyl azide (5.00g, 26.05mmol) in carbon tetrachlori...

Embodiment 3

[0070] N'-(4-tolyl)-3-(uracil-5-sulfonamido)phenylurea A3 was prepared as in Example 1

[0071] 1 H NMR (600MHz, DMSO-d 6 )δ11.81(br.s.,1H),11.62(br.s.,1H),10.13(br.s.,1H),8.70(br.s.,1H),8.52(br.s., 1H),8.05(br.s.,1H),7.57-7.22(m,3H),7.20-6.91(m,4H),6.70(d,J=7.3Hz,1H),2.24(s,3H)MS (ESI,m / z):414.40[M-H] - .

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Abstract

The invention belongs to the field of medicines, and particularly relates to a pyrimidine phenylurea anti-tumor compound and a preparation method and application thereof. A structure general formula of the pyrimidine phenylurea anti-tumor compound is specifically as shown in the description. The compound has a certain inhibitory activity to a human lung cancer H460 cell, a cervical cancer Hela cell, and a human ovarian cancer OVCAR3 cell. In a synthetic process, the synthetic procedures are simplified, and the possibility is provided for the future industrial production.

Description

technical field [0001] The invention belongs to the field of medicine, and in particular relates to a pyrimidine phenylurea antitumor compound and a preparation method and application thereof. Background technique [0002] At this stage, there are four main ways to treat cancer clinically: surgery, radiation therapy, chemotherapy, and immunotherapy. Compared with the other three methods, chemical drug treatment is generally painless, and its lethality to cancer cells is difficult to achieve by other means of treating cancer. However, most chemotherapy drugs are not specific. While killing cancer cells, they will cause damage to normal tissue cells around the tumor. These tissues can usually repair themselves after chemotherapy. Therefore, finding highly targeted, efficient and safe anti-tumor drugs has become one of the research hotspots of global pharmaceutical developers. [0003] Traditional anticancer drug screening targets mostly test the direct toxicity of substances...

Claims

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Application Information

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IPC IPC(8): C07D239/60A61K31/513A61P35/00
CPCA61P35/00C07D239/60
Inventor 孟繁浩李馨阳卢国庆李帅何鑫刘凯利
Owner 中国医科大学
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