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

A derivative, 2-b technology, used in antitumor drugs, medical preparations containing active ingredients, organic chemistry, etc., can solve the problems of unsatisfactory effect, insufficient source and low selectivity

Inactive Publication Date: 2007-03-14
DALIAN UNIV OF TECH
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  • 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

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  • 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

[0041]

[0042] 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 CH2-, 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

[0044]

[0045] 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

[0047]

[0048] 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, 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).

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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

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Application Information

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