Anti-tumor medicament structure

A technology of drugs and compositions, applied in the field of new anti-tumor drug structures, can solve problems such as toxic side effects and poor selectivity

Inactive Publication Date: 2011-05-25
FOURTH MILITARY MEDICAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] However, the existing anti-tumor drugs have problems such as poor selectivity, toxic side effects, and drug resistance.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Embodiment 1: the synthetic method of compound 1

[0020]

[0021] 1.22 g (10.0 mmol) of p-hydroxybenzaldehyde and 1.48 g (10.0 mmol) of dihydroxylamine were dissolved in 50 mL of methanol and refluxed for 24 h. A large amount of white insoluble matter was formed, filtered, and the filter cake was washed with a small amount of methanol. Suspend the filter cake in 50.0 mL CH 2 Cl 2 , cooled in an ice-water bath, and added 30.0 mL NaIO 4 (1.7 g) aqueous solution, the reaction was stopped after stirring for 15 min. After static separation, the aqueous phase was washed with CH 2 Cl 2 Extracted twice, combined the organic phases, dried overnight, filtered, removed the solvent under reduced pressure, and purified by column chromatography to obtain 1.12 g of the product, with a yield of 45%. Mp: 137-139℃.R f =0.33 (CHCl 3 / CH 3 OH, 20:1). EI-MS(m / z) 250.1[M] + .IR(KBr) 3340 (OH); 1590, 1450, 1380, 880, 800, 690 cm -1 . Anal. Calcd for C 13 h 17 N 2 o 3 : C,...

Embodiment 2

[0022] Embodiment 2: the synthetic method of compound 2

[0023]

[0024] 1.88 g (10.0 mmol) of p-3,4-dichlorobenzaldehyde and 1.48 g (10.0 mmol) of dihydroxylamine were dissolved in 50 mL of methanol and refluxed for 24 h. A large amount of white insoluble matter was formed, filtered, and the filter cake was washed with a small amount of methanol. Suspend the filter cake in 50.0 mL CH 2 Cl 2 , cooled in an ice-water bath, and added 30.0 mL NaIO 4 (1.7 g) aqueous solution, the reaction was stopped after stirring for 15 min. After static separation, the aqueous phase was washed with CH 2 Cl 2 Extract twice, combine the organic phases, dry overnight, filter, remove the solvent under reduced pressure, and purify by column chromatography to obtain 1.55 g of the product with a yield of 51%. Mp: 123-125℃. R f = 0.54(CHCl 3 / CH 3 OH, 20:1). EI-MS (m / z) 302 [M] + .IR (KBr) 1590, 1450, 1365, 1000, 825, 870 cm_1. Anal. Calcd for C 13 h 15 N 2 o 2 Cl 2 : C, 51.67; H,...

Embodiment 3

[0025] Embodiment 3: the synthetic method of compound 3

[0026]

[0027] 1.53 g (10.0 mmol) of p-fluoroformaldehyde and 1.48 g (10.0 mmol) of dihydroxylamine were dissolved in 50 mL of methanol and refluxed for 24 h. A large amount of white insoluble matter was formed, filtered, and the filter cake was washed with a small amount of methanol. Suspend the filter cake in 50.0 mL CH 2 Cl 2 , cooled in an ice-water bath, and added 30.0 mL NaIO 4 (1.7 g) aqueous solution, the reaction was stopped after stirring for 15 min. After static separation, the aqueous phase was washed with CH 2 Cl 2 Extract twice, combine the organic phases, dry overnight, filter, remove the solvent under reduced pressure, and purify by column chromatography to obtain 1.40 g of the product with a yield of 56%. Mp: 112-114℃.R f =0.52 (CHCl 3 / CH 3 OH, 20:1). EI-MS (m / z) 251 [M] + .IR (KBr) 1610, 1450, 1370, 1135, 770 cm -1 .ESR: a N =8.15G, g = 2.00996.

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Abstract

The invention provides a novel anti-tumor medicament structure which is shown by a structural general formula (I). In the formula, R1 to R5 are independently selected from H, NO2, OH, halogen and OCH3. The medicament has a simple and convenient synthesis method, and molecules comprise nitroxide free radical structure units, so the anti-tumor medicament structure can effectively suppress proliferation of liver cancer, stomach cancer, breast cancer and ovarian cancer cells.

Description

technical field [0001] The invention provides a class of novel antitumor drug structure, which belongs to the technical field of medicine. Background technique [0002] Malignant tumors seriously threaten human life and health. About 7 million people die from cancer every year in the world, accounting for about a quarter of the total death toll. Among them, breast cancer and ovarian cancer are the main malignant tumors that endanger women's health. About 1.2 million women in the world suffer from breast cancer every year. Gastric cancer is the most common malignant tumor in my country, and its death rate accounts for the first place among all kinds of malignant tumors. Liver cancer is the second cancer "killer" in my country, and it has jumped to the first place in some high-incidence areas of liver cancer, accounting for 45% of liver cancer deaths worldwide. At present, the mortality rate of cancer patients in our country exceeds 30%, which has become the second largest f...

Claims

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Application Information

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IPC IPC(8): C07D233/22C07D233/20A61K31/4164A61P35/00
Inventor 孙晓莉王海波田敏秦向阳向卓
Owner FOURTH MILITARY MEDICAL UNIVERSITY
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