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

Benzyl piperazine compound with anti-inflammatory activity as well as preparation method and medical application thereof

A technology of benzylpiperazine and compounds, applied in the field of medicinal chemistry, can solve problems such as side effects and threats to the safety of patients' lives

Active Publication Date: 2019-12-27
ANHUI UNIVERSITY OF TRADITIONAL CHINESE MEDICINE +2
View PDF6 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Existing anti-inflammatory drugs seriously threaten the life safety of patients due to side effects caused by excessive inhibition of a single target

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
  • Benzyl piperazine compound with anti-inflammatory activity as well as preparation method and medical application thereof
  • Benzyl piperazine compound with anti-inflammatory activity as well as preparation method and medical application thereof
  • Benzyl piperazine compound with anti-inflammatory activity as well as preparation method and medical application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0077] Synthesis of 1-(2-(4-(4-chlorobenzyl)piperazine-1-carbonyl)phenyl)ethanone (4a)

[0078] Step 1: Synthesis of 2-vinylbenzoic acid (2)

[0079] In a dry 100mL round bottom flask, add methyltriphenylphosphonium ammonium bromide (7.15g, 20.0mmol) and potassium tert-butoxide (3.37g, 30.0mmol) successively, add anhydrous tetrahydrofuran (100.0mL) to dissolve, and react The solution was stirred at room temperature for 1 hour under nitrogen protection. Anhydrous THF solution of 2-formylbenzoic acid (1.5 g, 10.0 mmol) was slowly added dropwise to the reaction solution, and the reaction solution was refluxed and stirred for 12 hours. TLC [V (petroleum ether): V (ethyl acetate) = 2:1 as developing solvent] showed that the reaction was almost complete. 100 mL of saturated ammonium chloride solution was added to the reaction liquid. The reaction solution was transferred to a separatory funnel, the organic layer was separated, and the aqueous layer was extracted with dichlorometh...

Embodiment 2

[0085] Synthesis of 1-(2-(4-(4-methoxybenzyl)piperazine-1-carbonyl)phenyl)ethanone (4b)

[0086] Referring to the synthesis method of Example 1, using compound 3 (0.82g, 3mmol) and 1-(4-methoxybenzyl)piperazine (0.84g, 4 mmol) as raw materials, column chromatography purified to obtain 0.38g of a white solid , yield 35.9%. m.p.88.4~89.6℃. 1 H NMR (400 MHz, DMSO-d 6 )δ: 7.98 (dd, J=7.7, 1.2Hz, 1H, Ar-H), 7.63 (d, J=7.5, 1.3Hz, 1H, Ar-H), 7.55 (d, J=7.6, 1.4Hz, 1H,Ar-H),7.32-7.25(m,1H,Ar-H),7.25-7.18(m,2H,Ar-H),6.94–6.84(m,2H,Ar-H),3.73(s, 3H,CH 3 ), 3.57(d, J=5.1Hz, 2H, piperazine-H), 3.42(s, 2H, CH 2 ), 3.04(t, J = 5.0Hz, 2H, piperazine-H), 2.55(s, 3H, CH 3 ), 2.41(t, J=5.1Hz, 2H, piperazine-H), 2.26(t, J=5.0 Hz, 2H, piperazine-H). 13 C NMR (101MHz, DMSO-d 6 )δ: 199.22, 169.35, 158.78, 137.12, 135.80, 132.92, 130.54, 130.25, 130.12, 129.28, 127.41, 114.04, 61.78, 55.45, 52.47, 52.16, 45.75, 48-33.2 M+H] + .

Embodiment 3

[0088] Synthesis of 1-(2-(4-(4-cyanobenzyl)piperazine-1-carbonyl)phenyl)ethanone (4c)

[0089] Referring to the synthesis method of Example 1, using compound 3 (0.82 g, 3 mmol) and 1-(4-cyanobenzyl) piperazine (0.80 g, 4 mmol) as raw materials, column chromatography purified to obtain 0.48 g of a white solid, Yield 46.1%. m.p.143.6~145.6℃. 1 H NMR (400 MHz, DMSO-d 6 )δ: 7.98 (dd, J = 7.8, 1.2Hz, 1H, Ar-H), 7.80 (d, J = 8.2Hz, 2H, Ar-H), 7.64 (dd, J = 7.5, 1.3Hz, 1H, Ar-H), 7.59-7.49 (m, 3H, Ar-H), 7.29 (dd, J = 7.8, 1.2Hz, 1H, Ar-H), 3.60 (d, J = 4.4Hz, 4H, piperazine-H ,CH 2 ), 3.06(t, J=5.0Hz, 2H, piperazine-H), 2.56(s, 3H, CH 3 ), 2.46(t, J=5.1Hz, 2H, piperazine-H), 2.30(t, J=5.0Hz, 2H, piperazine-H); 13 C NMR (101MHz, DMSO-d 6 )δ: 199.22, 169.41, 144.61, 137.07, 135.70, 132.98, 132.65, 130.33, 130.01, 129.32, 127.40, 110.23, 61.60, 52.53, 52.29, 46.70, 41.58-0, 28.31.ESI H] + .

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 benzylpiperazine compound (I) with anti-inflammatory activity and a preparation method thereof; pharmacodynamic tests prove that the compound provided by the invention has a COX-2, NF-[kappa]B and p38 MAPK multi-target inhibition effect, so that the compound can be used for preventing and treating inflammation-related diseases.

Description

technical field [0001] The invention relates to the field of medicinal chemistry, in particular to a class of benzylpiperazine compounds with anti-inflammatory activity, a preparation method and a medical application. Background technique [0002] Inflammation is an adaptive response of the body to external stimuli or cell damage. It maintains the stability of the body's internal environment by clearing inflammatory factors and repairing damaged tissues. Although the inflammatory response is essential to maintain the body's health, uncontrollable inflammatory responses can participate in the occurrence of many chronic diseases, such as asthma, atherosclerosis, rheumatoid arthritis, and cancer [Sun S, Ji Y, Kersten S, et al. Mechanisms of inflammatory responses in obese adipose tissue [J]. Annual Review of Nutrition, 2012(1): 261-286]. Therefore, anti-inflammatory drugs, which are widely used in clinical practice, have become one of the most used drugs. [0003] At present,...

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): C07D295/192C07D317/58C07D319/18C07D241/12C07D213/40A61K31/495A61K31/496A61K31/497A61P29/00A61P19/02A61P19/06A61P19/08A61P17/06A61P17/00A61P19/00A61P1/04A61P7/06A61P25/00A61P11/02A61P31/04A61P31/12A61P1/00
CPCC07D295/192C07D317/58C07D319/18C07D241/12C07D213/40A61P29/00A61P19/02A61P19/06A61P19/08A61P17/06A61P17/00A61P19/00A61P1/04A61P7/06A61P25/00A61P11/02A61P31/04A61P31/12A61P1/00
Inventor 李家明何广卫马晓东刘万冬刘为中储昭兴侯彩云许勤龙黄元政金帆莫佳佳
Owner ANHUI UNIVERSITY OF TRADITIONAL CHINESE MEDICINE
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