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Preparation method of diarylpyrazolylaniline compounds, and application of compounds in colorectal cancer treatment

A technology of diarylpyrazoleanilines and compounds, applied in the preparation of diarylpyrazoleanilines and their application in the treatment of colon cancer, which can solve the problems of low clinical cure rate

Inactive Publication Date: 2013-08-21
NANJING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] Cancer is a disease that seriously threatens human health, and the clinical cure rate is very low

Method used

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  • Preparation method of diarylpyrazolylaniline compounds, and application of compounds in colorectal cancer treatment
  • Preparation method of diarylpyrazolylaniline compounds, and application of compounds in colorectal cancer treatment
  • Preparation method of diarylpyrazolylaniline compounds, and application of compounds in colorectal cancer treatment

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] Example 1: Preparation of N-(4-oxyethylphenyl)-3-(4-methylbenzene)-1-phenyl-1H-pyrazole-4-aniline (compound 1)

[0018]

[0019] Dissolve p-methylacetophenone (20mmol), phenylhydrazine hydrochloride (25mmol) and anhydrous sodium acetate (40mmol) in ethanol respectively, stir magnetically, and react at 50-60°C for 4h (TLC to check the progress of the reaction). After the completion of the reaction, the reaction solution was spin-dried, ethyl acetate and water were extracted 2-3 times, and the organic layer was spin-dried to obtain a solid. Combine DMF and POCl 3 (12ml) Mix in an ice bath for 15 minutes, then dissolve the above solid in 3ml DMF and add dropwise to the above mixed solution, and gradually transfer to room temperature to 70-80°C for 5 hours. After cooling to normal temperature, pour into ice water, adjust pH to 7-8 with 50% NaOH, filter with suction and wash with water 3 times, and dry to obtain a solid. The resulting product was dissolved in acetone (30ml), a...

Embodiment 2

[0020] Example 2: Preparation of N-(4-oxyethylphenyl)-3-(4-oxymethylbenzene)-1-phenyl-1H-pyrazole-4-aniline (compound 2)

[0021]

[0022] The preparation method is the same as in Example 1. Substituting p-oxymethylacetophenone for the p-methylacetophenone in Example 1 to obtain the target compound in white crystal form. The yield is 68%, mp: 232-234°C; 1H NMR (300MHz, DMSO-d6, δppm): 8.54 (s, 1H); 7.60 (d, J = 8.12 Hz, 2H); 7.54 (d, J = 9.23 Hz, 4H); 7.50 (m, 3H); 7.35 (m, 3H); 6.84 (d, J = 8.79 Hz, 2H); 4.01 (dd, J = 14.07 Hz, 2H); 3.88 (s, 3H); 1.39 (t, J = 6.97 Hz, 3H). MS (ESI): 413.17 (C 25 H 24 N 3 O 3 [M+H]+).Anal.Calcd for C 25 H 23 N 3 O 3 : C, 72.62; H, 5.61; N, 10.16; O, 11.61. Found: C, 75.42; H, 5.56; N, 10.43; O, 11.46

Embodiment 3

[0023] Example 3: Preparation of N-(4-chlorophenyl)-3-(4-chlorobenzene)-1-phenyl-1H-pyrazole-4-aniline (compound 3)

[0024]

[0025] The preparation method is the same as in Example 1. Substitute p-chloroacetophenone for p-methylacetophenone in Example 1, and p-chloroaniline for p-ethoxyaniline in Example 1, to obtain the target compound in white crystal form. Yield 76%, melting point: 187-188°C; 1H NMR (300MHz, DMSO-d6, δppm): 8.56 (s, 1H); 7.72 (m, 4H); 7.52 (m, 4H); 7.29 (m, 7H) ).MS(ESI):408.28(C 22 H 16 Cl 2 N 3 O[M+H]+).Anal.Calcdfor C 22 H 15 Cl 2 N 3 O; C, 64.72; H, 3.70; Cl, ​​17.37; N, 10.29; O, 3.92. Found: C, 64.54; H, 3.66; Cl, ​​17.23; N, 10.15; O, 3.84.

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Abstract

Diarylpyrazolylaniline compounds are characterized in that the compounds have a general formula shown in the specification; and in the general formula, R1 is 4-Cl, a nitro group, a methyl group or a methoxy group, and R2 is 4-Br, Cl, a methoxy group or an oxyethyl group. The above diarylpyrazolylaniline derivatives can inhibit HCT116 propagation, so the above pyrazoline derivatives can be used as latent colorectal cancer prevention medicines. The invention discloses a preparation method of the compounds.

Description

Technical field [0001] The invention relates to a diarylpyrazole aniline compound, a preparation method thereof and an antitumor medicine. Background technique [0002] Cancer is a serious threat to human health, and the clinical cure rate is very low. Almost all cancers are caused by abnormal cell proliferation and are closely related to the mutation and inactivation of genes and proteins that regulate the cell cycle. Therefore, blocking abnormal cell proliferation is a very important means for tumor treatment. [0003] Aurora kinase is an important regulatory kinase in mitosis and is closely related to the normal growth and proliferation of cells. Aurora has three main family members: Aurora-A, Aurora-B and Aurora-C. Among them, Aurora-A is the most important. Abnormally high expression of Aurora-A protein can lead to the occurrence of many kinds of tumors. Therefore, Aurora-A kinase has become An important target for tumor therapy. [0004] At present, there are many small mol...

Claims

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Application Information

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IPC IPC(8): C07D231/14A61P35/00
Inventor 朱海亮卢翔李蹊杨先辉
Owner NANJING UNIV
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