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Salicylanilide derivatives, preparation method thereof and application thereof

A technology of salicylanilide and its derivatives, which is applied in the field of salicylanilide derivatives and their production methods and uses, can solve the problems of limited application, achieve strong specific binding ability, inhibit signal transduction and growth and division Effect

Inactive Publication Date: 2010-04-28
南京大学中国医药城研发中心
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there are 5-fluorouracil, cisplatin, and interferon-α in the clinical treatment of liver cancer, but these drugs have strong side effects, which limit their clinical application.

Method used

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  • Salicylanilide derivatives, preparation method thereof and application thereof
  • Salicylanilide derivatives, preparation method thereof and application thereof
  • Salicylanilide derivatives, preparation method thereof and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Example 1: Preparation of 2-hydroxy-6-methyl-N-phenylbenzamide (compound 1)

[0021]

[0022] Add 1mmol 6-methylsalicylic acid and 1mmol aniline, 100mg of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC·HCl) in a 50ml single-necked round bottom flask as a catalyst, and add 5 ml of anhydrous CH 2 Cl 2 as a reaction solvent. Stir with a magnetic stirrer and heat to reflux at 40°C in an oil bath. After reacting for 8 hours, a clear reaction solution is obtained. Add 40ml of 200-300 mesh column chromatography silica gel to the reaction solution, and rotate under reduced pressure with a rotary evaporator to remove excess solvent and make it fully mixed. The target product was separated by column chromatography, and eluted with a mixed solvent of ethyl acetate:petroleum ether=1:3. The obtained eluent was again distilled under reduced pressure with a rotary evaporator to remove the solvent to obtain the target compound in the form of white powder. Yiel...

Embodiment 2

[0023] Example 2: Preparation of N-(2-bromophenyl)-2-hydroxyl-6-methylbenzamide (compound 2)

[0024]

[0025] The preparation method is the same as in Example 1. 2-Br aniline was used instead of aniline to give the target compound as a white powder. Yield 83%. Mp165-167℃. 1 H NMR (500MHz, d 6 -DMSO): 2.31 (s, 3H); 6.81-6.84 (m, 2H); 7.10-7.13 (m, 1H); 7.40-7.43 (m, 1H); 7.70 (dd, J 1 = 1.5Hz,J 2 =8.3Hz, 1H); 7.93(dd, J 1 = 1.5Hz,J 2 = 8.0Hz, 1H); 8.29(dd, J 1 = 1.5Hz,J 2 =8.3Hz, 1H); 10.68(s, 1H); 11.83(s, 1H).MS(ESI): 307.2(C 14 h 13 BrNO 2 ,[M+H] + ).Anal.Calcd for C 14 h 12 BrNO 2 : C, 54.92; H, 3.95; Br, 26.10; N, 4.58%; Found: C, 55.01; H, 3.94; Br, 26.07; N, 4.59%.

Embodiment 3

[0026] Example 3: Preparation of N-(4-fluorophenyl)-2-hydroxyl-6-methylbenzamide (compound 3)

[0027]

[0028]The preparation method is the same as in Example 1. 4-Fluoroaniline was substituted for aniline to give the target compound as a white powder. Yield 81%. Mp 135-137°C. 1 H NMR (300MHz, d 6 -DMSO): 2.30(s, 3H); 6.79(d, J=4.4Hz, 2H); 7.21(t, J=9.0Hz, 2H); 7.69-7.73(m, 2H); 7.89(d, J= 8.2Hz, 1H); 10.34(s, 1H); 11.90(s, 1H). MS(ESI): 246.3(C 14 h 13 FNO 2 ,[M+H] + ).Anal.Calcd for C 14 h 12 FNO 2 : C, 68.56; H, 4.93; F, 7.75; N, 5.71%; Found: C, 68.69; H, 4.89; F, 7.72; N, 5.69%.

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Abstract

The invention discloses salicylanilide derivatives, which have the following general formula, wherein R1 is H or Br; R2 is H or Br; R3 is H or CH3; R4 is F, Cl, Br or I; R5 is F, Cl, Br or I; and R6 is CH3, OCH3, CH(CH3)2 or halogen. The salicylanilide derivatives have obvious inhibiting effect on HEP-G2 and EGFR in liver cancer cells, so the salicylanilide derivatives can be applied in preparing a medicament against liver cancer. The invention discloses a preparation method for the salicylanilide derivatives.

Description

technical field [0001] The present invention relates to salicylanilide derivatives and their preparation method and use. Background technique [0002] Salicylanilide derivatives are a class of compounds with a wide range of uses. It uses salicylic acid as a parent and combines with aniline derivatives with aromatic rings through amide bonds. Since the structure contains amide bonds with different substitutions, and the asymmetric unit is a common structural feature of many enzyme inhibitors and biomimetic peptides, most of them are biologically active. Widely used in pesticides, many of which can be used as herbicides, insecticides, fungicides and plant growth regulators, etc., also play a pivotal role in the fields of medicine and biology, some are important intermediates, and some asymmetric substitution compounds It can also be used as a CSP (chiral stationary phase) in chiral separation chromatography columns. In particular, in 2004, scientists reported that several sa...

Claims

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Application Information

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IPC IPC(8): C07C235/64C07C231/02A61K31/609A61P35/00A61P1/16
Inventor 朱海亮祝祯伟石磊杨莹
Owner 南京大学中国医药城研发中心
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