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

Substituted diaryl compound as well as preparation method and application thereof

A compound, -br technology, applied in the field of medicinal chemistry, can solve the problems of undisclosed pharmacological effects and no anti-tumor effects

Active Publication Date: 2021-09-14
SHANDONG FIRST MEDICAL UNIV & SHANDONG ACADEMY OF MEDICAL SCI
View PDF4 Cites 6 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The current published literature only has the physical and chemical properties of the compound, and there is no disclosure of its pharmacological effects, let alone any literature reports on its anti-tumor effect.

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
  • Substituted diaryl compound as well as preparation method and application thereof
  • Substituted diaryl compound as well as preparation method and application thereof
  • Substituted diaryl compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0077] Example 1: 1-(2-Ethoxyphenoxy)-3-((3-methoxy-4-(2-(4-methylpiperidin-1-yl)ethoxy)benzyl Synthesis of )(methyl)amino)propan-2-ol (SAMS10)

[0078]

[0079] Compound 5 used was 1-(3-methoxy-4-(2-(4-methylpiperidin-1-yl)ethoxy)phenyl)-N-methylmethanamine (5-1).

[0080] The compound 7 used was 2-((2-ethoxyphenoxy)methyl)oxirane (7-1).

[0081] 2-((2-Ethoxyphenoxy)methyl)oxirane (7-1) (194 mg, 1.0 mmol) and 1-(3-methoxy-4-(2-(4- Methylpiperidin-1-yl)ethoxy)phenyl)-N-methylmethanamine (5-1) (354 mg, 1.2 mmol) was dissolved in isopropanol (15 mL), under nitrogen protection, added catalytic The amount of pyridine (8.0 μL, 0.1 mmol) was heated to reflux for 6 h, and TLC detection (developing solvent: dichloromethane-methanol=10:1) raw material disappeared. The reaction solution was diluted with ethyl acetate, the organic phase was washed with water and saturated brine successively, dried over anhydrous sodium sulfate, filtered, and the solvent was distilled off under redu...

Embodiment 2

[0083] Example 2: 1-(2,6-Dichlorophenoxy)-3-((3-methoxy-4-(2-(4-methylpiperidin-1-yl)ethoxy)benzyl Synthesis of (methyl)(methyl)amino)propan-2-ol (CHJ02029)

[0084]

[0085] Compound 5 used was 1-(3-methoxy-4-(2-(4-methylpiperidin-1-yl)ethoxy)phenyl)-N-methylmethanamine (5-1).

[0086] The compound 7 used was 2-((2,6-dichlorophenoxy)methyl)oxirane (7-2).

[0087] Colorless oil, 88% yield, 1 H NMR (CD 3 OD,400MHz)δ(ppm):7.36(d,J=8.0Hz,2H),7.08(t,J=8.0Hz,1H),7.01(s,1H),6.87(m,2H),4.15(m ,3H),3.99(m,2H),3.80(s,3H),3.59(m,2H), 3.14(d,J=11.20Hz,2H),2.92(t,J=5.60Hz,2H),2.74 (m, 1H), 2.59(dd, J=12.80, 7.60Hz, 1H), 2.32(m, 5H), 1.70(d, J=12.80Hz, 2H), 1.45(s, 1H), 1.30(m, 2H), 0.95(d, J=6.4Hz, 3H). 13 CNMR(CD 3 OD, 100MHz)δ(ppm): 151.27,149.68,147.30,131.70,129.04,128.89(3C), 125.31,121.62,113.84,113.09,75.76,67.86,66.25,62.02,59.27,53.80(2C) ,41.86, 33.04(2C),29.92,20.60.IR(KBr,cm -1 ): 2947, 2926, 2872, 2841, 2792, 2360, 2340, 1651, 1592, 1511, 1475, 1455, 1367, 1286, 1...

Embodiment 3

[0088] Example 3: 1-(4-Bromo-3-(trifluoromethyl)phenoxy)-3-((3-methoxy-4-(2-(4-methylpiperidin-1-yl) )ethoxy)benzyl)(methyl)amino)propan-2-ol (CHJ02049) Synthesis

[0089]

[0090] Compound 5 used was 1-(3-methoxy-4-(2-(4-methylpiperidin-1-yl)ethoxy)phenyl)-N-methylmethanamine (5-1).

[0091] Compound 7 used was 2-((4-bromo-3-(trifluoromethyl)phenoxy)methyl)oxirane (7-3).

[0092] Colorless oil, 87% yield, 1 H NMR (CD 3 OD,400MHz)δ(ppm): 7.64(d,J=8.80Hz,1H),7.26(s,1H),7.02(d,J=8.80Hz,1H),6.95(s,1H),6.83(q , J=8.0Hz, 2H), 4.08(m, 4H), 3.91(m, 1H), 3.75(s, 3H), 3.50(q, J=12.80Hz, 2H), 3.03(d, J=11.60Hz ,2H),2.80(t,J=5.60Hz,2H),2.62(dd,J=12.40,5.60Hz,1H),2.48(dd,J=12.40,6.40Hz,1H),2.32(s,3H) ,2.17(t,J=11.60Hz,2H),1.66(d,J=12.40Hz,2H),1.39(s,1H),1.29(m,2H),0.94(d,J=6.40Hz,3H) . 13 CNMR (CD 3 OD,100MHz)δ(ppm):158.33,149.62,147.45,135.7(2C),131.91,121.46(2C),118.91,114.35,114.29,113.48,113.06,70.99,67.29,66.69,62.29,548.70 ,54.00(2C),42.25, 33.48(2C),33.25,20.75.IR(KBr,cm ...

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 the field of medicinal chemistry, in particular to a substituted diaryl compound shown as a formula (I), a preparation method of the substituted diaryl compound, a medicinal preparation containing the substituted diaryl compound and medical application of the substituted diaryl compound. Pharmacological test results show that the substituted diaryl compound disclosed by the invention has a good inhibition effect on cells of human lung cancer (A549), human ovarian cancer (SKOV3), human melanoma (A375) and human colon cancer (LOVO). The formula (I) is shown in the specification.

Description

technical field [0001] The present invention relates to the field of medicinal chemistry, in particular to a class of substituted diaryl compounds, a preparation method thereof, and a medicinal preparation and medicinal use thereof. Background technique [0002] 1-(2-Ethoxyphenoxy)-3-((3-methoxy-4-(2-(4-methylpiperidin-1-yl)ethoxy)benzyl)(methyl ) amino) propan-2-ol, CAS No. 2125657-10-3, molecular formula C 28 H 42 N 2 O 5 , the structural formula is: [0003] [0004] At present, only the physicochemical properties of the compound are disclosed in the literature, and there is no disclosure of its pharmacological action, and no literature report that it has an anti-tumor effect. SUMMARY OF THE INVENTION [0005] The technical problem solved by the present invention is to provide a class of substituted diaryl compounds and their pharmaceutically acceptable salts, their optical isomers, their preparation methods, pharmaceutical compositions and their applications in...

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): C07D211/22C07D233/64C07D295/088C07C217/18C07C213/02A61K31/44A61K31/4164A61K31/40A61K31/138A61P35/00
CPCC07D295/088A61P35/00C07D211/14C07C217/58C07D233/60Y02P20/55C07C217/64C07D207/06C07D211/82
Inventor 刘波姚庆强陈海蛟杨新美智英李莹汪海洋崔正国刘效祥扈国栋丁天地张飞鹏
Owner SHANDONG FIRST MEDICAL UNIV & SHANDONG ACADEMY OF MEDICAL SCI
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