Supercharge Your Innovation With Domain-Expert AI Agents!

3-(2-naphthyl) acrylamide derivatives as well as preparation method and application thereof

A technology of acrylamide and its derivatives, which is applied in the field of 3-(2-naphthyl)acrylamide derivatives and their preparation and application, and can solve the problems of preventing the growth of malignant tumors, etc.

Inactive Publication Date: 2012-08-22
NANJING AGRICULTURAL UNIVERSITY
View PDF1 Cites 2 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

It can be seen that once the activity of EGFR is inhibited, it is possible to greatly prevent the growth of malignant tumors

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
  • 3-(2-naphthyl) acrylamide derivatives as well as preparation method and application thereof
  • 3-(2-naphthyl) acrylamide derivatives as well as preparation method and application thereof
  • 3-(2-naphthyl) acrylamide derivatives as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Example 1: Preparation of 3-(2-naphthyl)acrylanilide (compound 1)

[0021]

[0022] Freshly prepared 3-(2-naphthyl)acryloyl chloride (1 mmol) was dissolved in anhydrous CH 2 Cl 2 (30mL), add NaHCO 3 (0.5g), stirred for 5min, added DMAP (5mg), continued to stir for 5min, added aniline (1mmol) into the system, and refluxed at 40-50°C for 5h. The reaction solution was washed successively with 5% HCl aqueous solution (50mL), 5% NaOH aqueous solution (50mL) and clear water (50mL) for 3 times each, and the organic phase was taken and washed with anhydrous Na 2 SO 4 After drying, the solvent was removed under reduced pressure, and silica gel column chromatography was performed using a mixed solvent of petroleum ether: ethyl acetate = 5:1 as the eluent. The eluate was evaporated under reduced pressure to remove the solvent, and recrystallized in ethyl acetate solution to obtain the target compound as white needle crystals. Yield 75%. Mp: 161-163℃.ESI-MS ([M+H] + ): 27...

Embodiment 2

[0023] Example 2: Preparation of 3-(2-naphthyl)acryloyl-4-isopropylaniline (compound 2)

[0024]

[0025] The preparation method is the same as in Example 1. Substituting 4-isopropylaniline for aniline, the target compound was obtained as pale yellow needle-like crystals. Yield 68%. Mp: 174-175℃.ESI-MS ([M+H] + ): 316.2. 1 H-NMR (400 MHz, DMSO-d 6 , δ ppm): 1.21 (d, 6H), 2.84 (m, 1H), 6.89 (d, 1H), 7.28 (d, 2H), 7.30 (d, 1H), 7.48 (d, 1H), 7.59-7.62 (m, 4H), 7.77 (d, 1H), 7.86 (s, 1H), 8.12 (m, 2H), 9.70 (brs, 1H).

Embodiment 3

[0026] Example 3: Preparation of 3-(2-naphthyl)acryloyl-2-chloroaniline (compound 3)

[0027]

[0028] The preparation method is the same as in Example 1. Substituting 2-chloroaniline for aniline, the target compound was obtained as white needle-like crystals. Yield 70%. Mp: 152-154℃.ESI-MS ([M+H] + ): 308.2. 1 H-NMR (400MHz, DMSO-d 6 , δ ppm): 6.93(d, 1H), 7.17(m, 1H), 7.35(m, 1H), 7.42(d, 1H), 7.44(d, 1H), 7.55(m, 2H), 7.68(d , 1H), 7.73 (s, 1H), 7.85 (d, 1H), 7.99-8.03 (m, 3H), 9.23 (brs, 1H).

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 discloses 3-(2-naphthyl) acrylamide derivatives as well as a preparation method and application thereof. 3-(2-naphthyl) acrylamide-like compounds are characterized by having the following general formula: in the formula, R is an aromatic base, a heterocyclic radical and the like. The compounds as inhibitors of an epidermal growth factor receptor (EGFR) can be applied to targeted therapy of tumor cells. The invention discloses the preparation method of the 3-(2-naphthyl) acrylamide derivatives.

Description

technical field [0001] The invention relates to a class of 3-(2-naphthyl)acrylamide derivatives, a preparation method thereof and use as an epidermal growth factor receptor (EGFR) inhibitor. Background technique [0002] Chemotherapy of cancer has entered the era of molecular targeting. Compared with traditional cytotoxic drugs, molecular targeted drugs have higher selectivity and better safety (see: Seymore L. Cancer Treat. Rev. 1999, 25, 301.). Among many molecular targets, epidermal growth factor receptor (EGFR) has become the object of high attention and research in recent years. Epidermal growth factor (EGF) and its receptor, EGFR, located on the cell membrane, have been identified as important drivers of cell growth and reproduction. When EGF and other growth factors bind to the extracellular binding region of EGFR, the tyrosine kinase of EGFR will be activated, and then start a series of complex signal transduction pathways in the cell, and promote the transmission ...

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): C07C233/11C07C233/15C07D215/40C07D311/16C07D277/82C07D295/13C07C231/02A61P35/00
Inventor 叶永浩张矛朱海亮
Owner NANJING AGRICULTURAL UNIVERSITY
Features
  • R&D
  • Intellectual Property
  • Life Sciences
  • Materials
  • Tech Scout
Why Patsnap Eureka
  • Unparalleled Data Quality
  • Higher Quality Content
  • 60% Fewer Hallucinations
Social media
Patsnap Eureka Blog
Learn More

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

© 2025 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com