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Anti-tumour compound, pharmaceutically accepted salts as well as preparation method and application thereof

A compound and amine compound technology, applied in the field of new compounds in the field of medicinal chemistry, can solve the problems of high toxicity and side effects, low killing activity, etc., and achieve the effects of convenient industrial production, broad application prospects and simple preparation methods.

Inactive Publication Date: 2012-10-03
CHONGQING MEDICAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Tumor chemotherapy is a rapidly developing field. The future treatment of malignant tumors will be dominated by tumor chemotherapy. However, the chemical drugs used in current drug therapy have low killing activity on tumors and cancer cells and require large doses of drugs. , so that the toxic and side effects on the human body are higher, so it is urgent to develop new chemotherapeutic drugs with high killing activity on tumors and cancer cells

Method used

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  • Anti-tumour compound, pharmaceutically accepted salts as well as preparation method and application thereof
  • Anti-tumour compound, pharmaceutically accepted salts as well as preparation method and application thereof
  • Anti-tumour compound, pharmaceutically accepted salts as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Example 1: Preparation of (S)-N-1-(1-phenylethyl)-1-(4,4-bis(4-fluorophenyl))butylamine (Compound I-1, S0205):

[0035]

[0036] 4,4-bis(4-fluorophenyl)-1-chlorobutane (compound II-1, 0.50g, 1.78mmol) and (S)-1-phenylethylamine (compound III-1, S0205 , 0.53g, 3.58mmol) into DMSO (8mL) in a 25mL single-port reaction vial with magnetic stirring, and stirred at 80°C for 10 hours. The reactant was transferred to a 250mL separatory funnel, diluted with 100mL of ethyl acetate, and then diluted with 30mL of 5% Na 2 CO 3 Wash twice with aqueous solution, then wash twice with 50 mL of water, and finally wash once with saturated 50 mL of NaCl aqueous solution. Then the organic layer was dried over anhydrous sodium sulfate, filtered, concentrated, and purified by column chromatography to obtain (S)-N-1-(1-phenylethyl)-1-(4,4-bis(4-fluorophenyl) )) Butylamine (compound 1-1, S0205, 0.59 g, 91% yield). 1 H-NMR (CDCl 3 ,400MHz):7.33~7.21(m,5H),7.10(dd,J 1 =5.6Hz,J 2 =8.6Hz,4...

Embodiment 2

[0037] Example 2: Preparation of N-1-benzyl-1-(4,4-bis(4-fluorophenyl))butylamine (Compound I-2):

[0038]

[0039] Add 4,4-bis(4-fluorophenyl)-1-butaneamine (compound II-2, 1.87g, 7.16mmol) and benzyl chloride (compound III-2, S0154, 0.45g, 3.58mmol) Into DMSO (16 mL) in a 50 mL single-necked reaction vial with magnetic stirring and stir at 80 °C for 7 h. The reactant was transferred to a 50mL separatory funnel, diluted with 20mL of ethyl acetate, and then diluted with 5mL of 5% Na 2 CO 3 Wash twice with aqueous solution, then wash twice with 10 mL of water, and finally wash once with saturated 10 mL of NaCl aqueous solution. Then the organic layer was dried over anhydrous sodium sulfate, filtered, concentrated, and purified by column chromatography to obtain N-1-benzyl-1-(4,4-bis(4-fluorophenyl))butylamine (compound I-2 , 1.1g, 88% yield). 1 H-NMR (CDCl 3 ,400MHz):7.33~7.27(m,5H),7.10(dd,J 1 =5.5Hz,J 2 =8.6Hz,4H),6.92(t,J=8.6Hz,4H),3.82(s,2H),3.80(t,J=7.7Hz,1H),2.6...

Embodiment 3

[0040] Example 3: Preparation of N-1-(4,4-bis(4-fluorophenyl))butyl-1-(1H-2-indole)carboxamide (Compound I-3, S0161):

[0041]

[0042] (1H-2-indole) formic acid (compound III-3, 0.50g, 3.1mmol) and thionyl chloride (SOCl 2 , 5mL) into a 25mL single-port reaction flask with magnetic stirring, and stirred at reflux for 3 hours. Excess thionyl chloride was then removed under reduced pressure, followed by the addition of 5 mL of 4,4-bis(4-fluorophenyl)-1-butanean (compound II-3, 0.53 g, 2.06 mmol) in tetrahydrofuran and 4-(N,N-Dimethyl)pyridine (DMAP, 0.51g, 4.12mmol), and the reaction solution was stirred at room temperature for 12 hours. The reactant was transferred to a 50 mL separatory funnel, diluted with 20 mL of ethyl acetate, and then diluted with 20 mL of 5% Na 2 CO 3 Wash twice with aqueous solution, then wash twice with 10 mL of water, and finally wash once with saturated 10 mL of NaCl aqueous solution. Then the organic layer was dried over anhydrous sodium sulf...

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Abstract

The invention discloses an amine compound containing aromatic ring shown in the general formula I and salts thereof. In the formula, X represents CH or N atom; R1 represents H atom or F atom or chlorine atom or substituted alkyl or substituted alkoxy; R2 represents H atom or F atom or chlorine atom or substituted alkyl or substituted alkoxy; R3 represents phenyl or substituted alkyl or substituted phenyl or substituted pyridyl or substituted benzpyrole; Y represents substituted alkyl or substituted alkanoyl; and Y1 represents substituted alkyl or substituted alkanoyl. The invention also provides an application and preparation method of the compound in preparation of medicine for preventing and treating tumormetastasis, advanced cancer, non-entity cancer, and the like.

Description

technical field [0001] The present invention relates to a class of new compounds mainly used in the field of medicinal chemistry, in particular to a novel aromatic ring-containing amine compound and a preparation method thereof, and as a method for treating tumor diseases, especially tumor metastases, advanced tumors, non-solid tumors and other cancers. application in medicines. Background technique [0002] Cancer is a major disease that threatens national health at present. Malignant tumors are major diseases affecting people's health. According to WHO statistics, more than 11 million cases of malignant tumors occur every year in the world, and more than 8 million people die from them. The annual incidence of tumors in developed countries is higher than 300 / 100,000. According to national statistics, in the past two years, malignant tumors accounted for the first cause of death among urban residents in my country, and there were about 2.2 million new patients each year, a...

Claims

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Application Information

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IPC IPC(8): C07C211/29C07D209/42A61K31/137A61K31/404A61P35/00
Inventor 李雁武许红霞袁建勇贾云灿胡叶敏
Owner CHONGQING MEDICAL UNIVERSITY
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