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3-amido substituted nenzoyl urea compound, and its antitumor action

A compound and anti-tumor drug technology, applied in the field of microtubule and microfilament inhibitor benzoyl urea small molecule derivatives, can solve the problems such as the anti-tumor effect of compounds that have not yet been seen, and achieve the effect of strong cell killing activity

Inactive Publication Date: 2006-10-25
MEDICINE & BIOENG INST OF CHINESE ACAD OF MEDICAL SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

So far, there have been no reports related to the compounds of the present invention and their antitumor effects

Method used

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  • 3-amido substituted nenzoyl urea compound, and its antitumor action
  • 3-amido substituted nenzoyl urea compound, and its antitumor action
  • 3-amido substituted nenzoyl urea compound, and its antitumor action

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] : Preparation of enantiomers (-)-JIMB01 and (+)-JIMB01

[0017] Preparation of chiral side chains: Dissolve 0.46g (0.30mmol) of 2-bromopropionic acid in 10ml of anhydrous dichloromethane, add 0.54g (0.45mmol) of thionyl chloride, heat to reflux for 2h, evaporate the solvent and excess Thionyl chloride can be obtained.

[0018] 13.7g (0.1mol) of 3-aminobenzoic acid was dissolved in 100ml of ethyl acetate (EA), and 15.53ml (0.11mol) of trifluoroacetic anhydride was added dropwise, and heated to reflux for 1h. The solid was filtered, washed thoroughly with EA, and dried to constant weight to obtain a white solid to obtain 3-(N-trifluoroacetylamino)benzoic acid (A-1), yield 86% (20.0 g), melting point: 285°C.

[0019] Dissolve 4.66g (0.02mol) of A-1 in 50ml of EA, add 15ml of thionyl chloride (SOCl2) dropwise, and heat to reflux until the reaction solution becomes a clear yellow liquid (1h). The solvent and the remaining SOCl2 were evaporated, and recrystallized with cycl...

Embodiment 2

[0029] : Preparation of 4-chlorobenzoylurea compounds F-1, F-2, F-3, F-4

[0030] Take 17.20g (0.1mol) of 4-chloro-3-aminobenzoic acid and dissolve it in 100ml of ethyl acetate (EA), add dropwise 15.53ml (0.11mol) of trifluoroacetic anhydride, and heat to reflux for 1h. The solid was filtered, washed thoroughly with EA, dried to constant weight to obtain a white solid, and 4-chloro-3-(N-trifluoroacetylamino)benzoic acid (B-1) was obtained in a yield of 91.2% (24.4g). Melting point: 158°C-160C.

[0031] Dissolve 5.35g (0.02mol) (B-1) in 50ml of EA, add 15ml of SOCl2 dropwise, and heat to reflux until the reaction solution becomes a clear yellow liquid (1h). Evaporate solvent and remaining SOCl2, and carry out recrystallization with cyclohexane to obtain pale yellow crystals, obtain 4-chloro-3-(N-trifluoroacetylamino) benzoyl chloride (B-2), yield 85% ( 4.86g), melting point: 98°C-100°C.

[0032] Dissolve 5.72g (0.02mol) (B-2) in 50ml of toluene, add 6.00g (0.1mol) of urea, s...

Embodiment 4

[0077] : Synthesis of 4-methylbenzoylurea compounds F-21, F-22, F-23, F-24

[0078] Take 15.1g (0.1mol) of 4-methyl-3-aminobenzoic acid and dissolve it in 100ml of ethyl acetate (EA), add dropwise 15.53ml (0.11mol) of trifluoroacetic anhydride, and heat to reflux for 1h. The solid was filtered, washed thoroughly with EA, and dried to constant weight to obtain a white solid to obtain 4-methyl-3-(N-trifluoroacetylamino)benzoic acid (D-1). Yield: 92.3% (22.81g), melting point: 174°C-176°C.

[0079] Dissolve (D-1) 4.94g (0.02mol) in 50ml EA, add dropwise 15ml SOCl2, and heat to reflux until the reaction solution becomes a clear yellow liquid (1h). The solvent and the remaining SOCl2 were evaporated, and recrystallized with cyclohexane to obtain pale yellow crystals to obtain 4-methyl-3-(N-trifluoroacetylamino)benzoyl chloride (D-2). Yield: 84.4% (4.48g), melting point: 108°C-110°C.

[0080] Dissolve 5.30g (0.02mol) of (D-2) in 50ml of toluene, add 6.00g (0.1mol) of urea, slowly...

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Abstract

This invention relates to new style 3-acylamino substituted benzoyl urea kind compound. On base of deep research of structure activity, benzene ring mother nuclide, 1 bit acyl urea side chain and 3 bit acyl urea side chain are differently replaced to synthesize series derivant. Good compound is selected from the derivant, and it has strong activity revealed by anti tumor experiment, and toxicity is low, so it is convenient to synthesize, and anti medicine capability is hard form, so it has good application prospect.

Description

Technical field: [0001] The invention relates to a microtubule microfilament inhibitor benzoylurea small molecule derivative and its antitumor effect. Background technique: [0002] Tumor is one of the malignant and stubborn diseases that are difficult to deal with, and it has become the second "killer" in the world after cardiovascular disease. According to the statistics of the World Health Organization, in 2000, the number of new cancer cases in the world exceeded 10 million, and the number of deaths was 6.2 million. In 2004, the number of patients exceeded 22 million. In 2020, the number of new cancer cases worldwide will reach 15 million and 10 million will die. According to literature reports, in addition to the bioengineering drugs (including anti-cancer vaccines) such as monoclonal antibodies, tumor necrosis factors, interferons, and interleukins that have been marketed, the anti-tumor drugs that are currently under development include the following 8 categories: ①A...

Claims

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Application Information

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IPC IPC(8): C07C275/54A61K9/00A61K31/17A61P35/00
Inventor 宋丹青杨鹏王妍武连宗蒋建东
Owner MEDICINE & BIOENG INST OF CHINESE ACAD OF MEDICAL SCI
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