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

Acenaphthene heterocyclic compound and its cell fading inducing and anti-tumor use

A compound and an apoptosis-inducing technology, which are applied to acenaphthene heterocyclic compounds and their application fields of inducing apoptosis and anti-tumor, and can solve the problems of unsatisfactory effect, large side effects, insufficient sources, etc.

Inactive Publication Date: 2005-05-18
DALIAN UNIV OF TECH
View PDF0 Cites 10 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These products all belong to vitamin A, non-steroidal anti-inflammatory drugs, polyphenols, vanilloids, and topoisomerase inhibitors. It can be seen that they are still mainly chemical synthesis products of natural medicines or their analogues, and there are sources Insufficient, expensive, low selectivity, large side effects, unsatisfactory effect, etc.

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
  • Acenaphthene heterocyclic compound and its cell fading inducing and anti-tumor use
  • Acenaphthene heterocyclic compound and its cell fading inducing and anti-tumor use
  • Acenaphthene heterocyclic compound and its cell fading inducing and anti-tumor use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042]

[0043] Add 0.46 g of 3-mercaptomethyl-propylamine to 50 ml of acetonitrile in 1 g of 8-oxo-8H acenaphtho[1,2-b]pyrrole-9-carbonitrile, stir at room temperature for 2 hours, evaporate part of the solvent, and precipitate the product 3- (3'-Mercaptomethyl-propyl)amino-8-oxo-8H-acenaphtho[1,2-b]pyrrole-9-carbonitrile A1, yield 60%. M.p.266-268℃; 1 H NMR (400M, DMSO): δ9.604 (br s, -NH-, 1H), 8.5-8.54 (d, J=7.6Hz, 1H), 8.2-8.21 (d, J=7.2Hz, 1H), 7.75-79(d, J=8.8Hz, 1H), 7.57-7.6(t, J=7.8Hz, 1H), 6.9-6.92(d, J=9.2Hz, 1H), 3.24(br s, -NHCH 2 CH 2 -, 2H), 2.82-2.84 (m, -NHCH 2 CH 2 CH 2 -, 2H), 2.42 (br s, -SCH 3 -, 3H), 1.89-1.91 (m, -NHCH 2 CH 2 CH 2 -, 2H); ESI-MS: [M+H] - (334m / z).

Embodiment 2

[0045]

[0046] Add 0.54 g of ethyl 4-aminobutyrate to 50 ml of acetonitrile in 1 g of 8-oxo-8H acenaphtho[1,2-b]pyrrole-9-carbonitrile, stir at room temperature for 30 minutes, evaporate part of the solvent, and precipitate the product 3- (3'-Carboxylate ethyl propyl)amino-8-oxo-8H-acenaphtho[1,2-b]pyrrole-9-carbonitrile A2, yield 65%. M.p.>300℃; 1 H NMR (400M, DMSO): δ9.20 (br s, -NH-, 1H), 8.84-8.86 (d, J=7.6Hz, 1H), 8.64-8.66 (d, J=7.2Hz, 1H), 7.95=7.97(d, J=8.8Hz, 1H), 7.74-7.78(t, J=7.8Hz, 1H), 6.80-6.82(d, J=9.2Hz, 1H), 4.14-4.19(q, -COOCH 2 CH 3 , 2H), 3.62-3.67 (m, -NHCH 2 CH 2 CH 2 -, 2H), 2.52-2.55 (m, -NHCH 2 CH 2 CH 2 COO-, 2H), 2.10-2.13 (m, -NHCH 2 CH 2 CH 2 COO-, 2H), 1.35-1.38(t, -COOCH 2 CH 3 , 3H); ESI-MS: [M+H] - (360m / z).

Embodiment 3

[0048]

[0049] Add 0.45 g of thiomorpholine to 50 ml of acetonitrile in 1 gram of 8-oxo-8H acenaphtho[1,2-b]pyrrole-9-carbonitrile, stir at room temperature for 2 hours, and separate the product 3-thiomorpholino by column chromatography -8-Oxo-8H-acenaphtho[1,2-b]pyrrole-9-carbonitrile and 6-thiomorpholino-8-oxo-8H-acenaphtho[1,2-b]pyrrole-9-carbonitrile A3 , and the yields were 40% and 30%, respectively. A3: Decompose at M.p.225℃; 1 H NMR (400M, DMSO): 8.69-8.71 (d, J=8.0Hz, 1H), 8.42-8.45 (d, J=8.2Hz, 1H), 7.98-7.96 (d, J=8.0Hz, 1H), 7.88-7.92(t, J=8.0Hz, 1H), 7.04-7.02(d, J=8.2Hz, 1H), 3.68(br s, -N(CH 2 CH 2 ) 2 S, 4H), 3.05(br s, -N(CH 2 CH 2 ) 2 S, 4H); ESI-MS: [M-H] - (330m / z).

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 present invention relates to a kind of amino group or halogen substituted 8-oxy-8H-acenaphthenee[1, 2-b] pyrrolyl-9-nitrile derivatives and their biological use. They are applied mainly in intracorporeal and extracorporeal inducing cell apoptosis and as anticancer compound. These compounds are 3, 6-disubstituted, 3-disubstituted or 6-substituted 8-oxy-8H-acenaphthenee[1, 2-b] pyrrolyl-9-nitrile derivatives. They can induce tumor cell apoptosis and block cell period in the dosage dependent mode within the wide concentration range of 0.01-10 micro mole. The highest activity compound B1 has IC50=0.17 micro mole (0.56 micro gram). When they are used in animal tumor model body, they can inhibit tumor growth obviously in inducing cell apoptosis mode. Therefore, the present invention is one kind of apoptosis inducing agent and antitumor compound with high activity.

Description

technical field [0001] The present invention relates to a class of amino or halogen substituted derivatives of 8-oxo-8H-acenaphtho[1,2-b]pyrrole-9-carbonitrile and their in vivo and in vitro induction of cell apoptosis and their anticancer compounds application. Background technique [0002] With the in-depth research on the process and mechanism of cell death, apoptosis has become a new target of anti-tumor drug research. Because the characteristic of tumor cells is to resist apoptosis and achieve "immortality" by evading the regulation of organism signals. Therefore, effective apoptosis inducers will fundamentally inhibit the survival of tumor cells and the continued atypia of precancerous lesions. Apoptosis inducers are of great value no matter as a tool for basic research in oncology or as a drug for clinical treatment of tumors. At present, many biological companies including Calbiochem (German), Merck (German), Promage (USA) and so on have developed and continue to ...

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
Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/403A61P35/00C07D209/56
Inventor 钱旭红张志超肖义刘凤玉吕哲
Owner DALIAN UNIV OF TECH
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