Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Novel substituted aminophenol compounds and preparation method and application thereof in field of medicine

An aminophenol and compound technology, applied in the field of substituted aminophenol compounds and their preparation, achieves the effects of significant anti-breast cancer activity, high yield and simple steps

Inactive Publication Date: 2015-09-09
SECOND MILITARY MEDICAL UNIV OF THE PEOPLES LIBERATION ARMY
View PDF2 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are no reports about a novel substituted aminophenol compound and its preparation method and its antitumor activity.

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Novel substituted aminophenol compounds and preparation method and application thereof in field of medicine
  • Novel substituted aminophenol compounds and preparation method and application thereof in field of medicine
  • Novel substituted aminophenol compounds and preparation method and application thereof in field of medicine

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0037] The present invention provides a substituted aminophenol compound with good anti-breast cancer activity, its preparation method and application, and its structure is shown in general formula A or B:

[0038]

[0039] Wherein, R is selected from a or b, and is connected with an ethoxy group through an amino group.

[0040] a.R is a secondary amine, (a) 1 to 6 carbon atom chain alkyl secondary amines, wherein the alkyl group can be straight or branched; (b) cycloalkyl secondary amines, wherein the cycloalkyl group includes cyclopentyl group, cyclohexyl, cycloheptyl and adamantyl;

[0041] b. R is a tertiary amine, (a) a chained alkyl tertiary amine with 1 to 6 carbon atoms, wherein the alkyl group can be a straight chain or a branched chain, and the two alkyl groups of the tertiary amine can be the same or different; ( b) alicyclic amines, including pyrrole, piperidine, piperazine and morpholine; (c) substituted piperidines and substituted piperazines, wherein the sub...

Embodiment 1

[0072] Embodiment 1 prepares intermediate 5

[0073] 1. Preparation of (2-(4-benzyloxy)phenoxy)ethanol

[0074]

[0075] Take 10.00g (0.05mol) of 4-benzyloxyphenol into a three-necked flask, add 50mL of water, heat to 80°C, add 63mL of 6% sodium hydroxide aqueous solution dropwise to a constant pressure dropping funnel under mechanical stirring, and the solution gradually becomes clear , 30 minutes to drop. Dissolve 12.5 g (0.10 mol) of bromoethanol in 20 mL of water, add dropwise to the above reaction solution through a constant-pressure dropping funnel, react at 80°C for 5 hours, adjust the pH to acidic, a white solid precipitates, extract with dichloromethane three times, wash with water twice Once, dried with saturated saline, and evaporated to dryness, recrystallized from dichloromethane and petroleum ether to obtain about 11.96 g of white crystals, with a yield of 98%. 1 H NMR (300MHz, CDCl 3 )δ3.91-3.94(m,2H),4.01-4.04(m,2H),5.01(s,2H),6.83-7.44(m,9H).

[0076] 2...

Embodiment 2

[0085] Embodiment 2 prepares intermediate 8

[0086] 1. Preparation of methyl 4-benzyloxyphenylacetate

[0087]

[0088] Weigh 20.00g (120.48mmol) of methyl p-hydroxyphenylacetate and dissolve it in 400mL of acetone, add 33.25g (240.96mmol) of potassium carbonate, then measure 16mL (132.53mmol) of benzyl bromide and add to the above reaction solution in batches. Stir at room temperature and react overnight. After the reaction, the solvent was evaporated to dryness, the solid was dissolved in dichloromethane, washed twice with water and once with saturated brine, and dried over anhydrous sodium sulfate. After filtering and evaporating the solvent to dryness, about 30.84 g of a colorless oil was obtained, with a yield of 97%. 1H NMR (300MHz, CDCl 3 )δ3.58(s,2H),3.69(s,3H),5.06(s,2H),6.93-7.45(m,9H).

[0089] 2. Preparation of 4-benzyloxyphenylacetic acid

[0090]

[0091] Take 30.84g (0.12mol) of methyl 4-benzyloxyphenylacetate and dissolve it in 100mL of methanol, ad...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention relates to novel substituted aminophenol compounds. The structure of the compounds is as shown in the general formula A or B, wherein R is selected from primary amine or tertiary amine, and an amino group is connected with an oxyethyl group. Through asymmetric synthesis, the substituted aminophenol compounds with different configurations can be obtained. Cell tests confirm that the compounds have a strong inhibitory activity to human breast cancer cells MDA-MB-231 and MCF-7, has a remarkable anti-breast cancer activity and can be used for preventing and curing breast cancer and curing female climacteric-related diseases such as osteoporosis and the like.

Description

technical field [0001] The present invention relates to the technical field of medicine, specifically, a new class of substituted aminophenol compounds with the activity of preventing and treating breast cancer, treating osteoporosis and other women's menopause-related diseases, its preparation method and its application in the field of medicine . Background technique [0002] Breast cancer is one of the malignant tumors that seriously threaten women's physical and mental health. Its incidence rate ranks first among female tumors in the world and shows an increasing trend year by year, and its mortality rate ranks second. The situation is not optimistic. [0003] At present, there are some effective drugs in the clinical treatment of breast cancer, but there are some common problems. The first is serious side effects, which bring pain to patients while killing tumor cells; the second is that the use of existing drugs makes tumor cells There is a certain resistance to drugs;...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
IPC IPC(8): C07D211/06C07C217/20C07C213/08C07D295/088C07D211/46A61P35/00A61P19/10
CPCC07D211/06C07C217/20C07D211/46C07D295/088
Inventor 徐明娟刘玉环丁浩夏蕾蕾陈雅郝璠严久琼
Owner SECOND MILITARY MEDICAL UNIV OF THE PEOPLES LIBERATION ARMY
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com