Novel benzylideneacetone derivative and use thereof

A technology of benzyloxy and hydroxyl, applied in the field of new benzylidene acetone derivatives, which can solve the problems of limited use and high cost of use

Pending Publication Date: 2020-04-10
韩药有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Novartis' Aclasta (zoledronate) and Eli Lilly's anabolic drug parathyroid hormone (Forsteo and Forteo (teriparatide) is effective, but its use is too expensive and its use is limited

Method used

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  • Novel benzylideneacetone derivative and use thereof
  • Novel benzylideneacetone derivative and use thereof
  • Novel benzylideneacetone derivative and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0200] Synthesis of novel compounds

[0201] To identify substances with anticancer activity and osteoclast differentiation inhibitory activity, the compounds were isolated and purified from the synthetic mixture of each compound, and the chemical structure of each compound was determined by nuclear magnetic resonance (NMR) and mass spectrometry (MS).

[0202] The synthesis method of each compound and the specific NMR and MS analysis results are as follows:

Embodiment 1-1

[0204] Synthesis of (E)-4-(4-fluoro-3-hydroxyphenyl)but-3-en-2-one (KP3)

[0205] 【Table 1】

[0206]

[0207] Under cooling, boron tribromide (1M dichloromethane solution, 10ml) was added dropwise to 3-methoxy-4-fluorobenzaldehyde ((3-methoxy-4-fluorobenzaldehyde, 1a) (440mg, 2.85mmol) In the dichloromethane solution, stirred at room temperature for 5 hours. The reaction solution was ice-cooled again, and cold water was slowly added to terminate the reaction, and then 5N hydrochloric acid solution was added dropwise until the pH was 1. The reaction solution was concentrated under reduced pressure, and the water and ethyl acetate were added to the residue, and the organic layer was separated. The organic layer was washed with saturated brine, dried with anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. By silica gel column chromatography (elution solvent: The obtained residue was purified by n-hexane-ethyl acetate 4:1) to obtain 210 mg...

Embodiment 1-2

[0212] Synthesis of (E)-4-(3-hydroxy-4-methylphenyl)but-3-en-2-one (KP2)

[0213] 【Table 2】

[0214]

[0215] Under cooling, boron tribromide (1M dichloromethane solution, 5mL) was added dropwise to 3-methoxy-4-methylbenzaldehyde (3-methoxy-4-methylbenzaldehyde, 1b) (400mg, 2.66mmol) dichloromethane solution and stirred at room temperature for 5 hours.

[0216] The reaction solution was ice-cooled again, cold water was slowly added to terminate the reaction, and then 5N hydrochloric acid solution was added dropwise until the pH was 1. The reaction solution was concentrated under reduced pressure, water and ethyl acetate were added to the residue, and the organic layer was separated. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. Purify the obtained residue by silica gel column chromatography (elution solvent: n-hexane-ethyl acetate 4:1) to obtain 3-hydroxyl-4-methylben...

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PUM

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Abstract

The present invention relates to a novel benzylideneacetone derivative or a use thereof and, more particularly, to a pharmaceutical composition for preventing or treating cancer or bone disease and afood composition for alleviating cancer or bone disease, each of the compositions comprising a compound represented by Chemical Formula 1 or a pharmaceutically acceptable salt thereof as an effectiveingredient. Exhibiting cancer cell-specific cytotoxicity and a potent activity of suppressing the growth and differentiation of osteoclasts, which cause bone loss, and promoting the proliferation anddifferentiation of osteoblasts, the compounds according to the present invention can find useful applications in developing a safe and effective anticancer agent and an agent for preventing or treating bone disease or a food for alleviating bone disease.

Description

technical field [0001] The present invention relates to a novel benzylideneacetone derivative or use thereof, more particularly to a prevention of cancer or bone disease comprising a compound represented by Chemical Formula 1 or a pharmaceutically acceptable salt thereof as an active ingredient Or a pharmaceutical composition for treatment, or a food composition for improvement. Background technique [0002] This application claims the priority of Korean Patent Application No. 10-2017-0095699 filed on July 27, 2017 and Korean Patent Application No. 10-2017-0099768 filed on August 7, 2017, all contents of the specification All are used as references of this application. [0003] With the aging society, cancer has become the leading cause of death. With the current development of surgery, anticancer chemotherapy, and radiation therapy, the cure rate of all types of cancer, including early and late stages, has exceeded 70%. However, due to technical limitations of surgical o...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/12A23L33/10C07C49/248
CPCA23L33/10A61K31/12C07C49/248C07C235/34C07C323/22C07D295/10C07D211/46C07B2200/09C07C49/217C07C49/223A23L33/40A61P19/08A61P35/00A23V2002/00C07C49/255
Inventor 朴吉洪具真谟李贞宪宋多云朴錫仁金汉谦李淳赫金洪珪帕提巴达·特瑞微妮金明焕
Owner 韩药有限公司
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