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New diketone piperazidine-like derivative and application thereof

A technology of diketopiperazines and derivatives, which is applied in the field of medicine, can solve the problems of limited curative effect, increased multidrug resistance and the like, and achieves the effect of strong activity and good activity

Inactive Publication Date: 2011-01-05
SHENYANG PHARMA UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The target of this type of compound is tubulin. By binding to tubulin, it prevents the formation of microtubules and keeps the mitosis of cells in the middle stage of division, thereby inhibiting the rapid proliferation of cancer cells. At present, this type of compound faces This is a big problem and the efficacy of this class of drugs has been limited due to the increasing multi-drug resistance

Method used

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  • New diketone piperazidine-like derivative and application thereof
  • New diketone piperazidine-like derivative and application thereof
  • New diketone piperazidine-like derivative and application thereof

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0016] Total synthesis method: (with n=1 in the general structural formula I series, R=N(CH 3 ) 2 example)

[0017] 1. 3-Hydroxy-4-geraniol benzaldehyde (pre-synthesis 1.0eq), bromochloropropane (1.0eq), triethylamine (1.0eq), dichloromethane as solvent, react in ice-water bath at 0°C for 30min, Silica gel column separation, the product was directly used in the next reaction. The product from the previous step (1.0eq), dimethylamine (1.0eq), triethylamine (cat), and dichloromethane were used as solvents; after mixing, they were stirred at room temperature for 5 hours and separated on a silica gel column to obtain the product (65%).

[0018] 2. Glycine methyl ester hydrochloride (1.0eq), L-alanine (Cbz protected amino group 1.0eq), add DCC (2.0eq), DMAP (cat), dichloromethane as solvent, mix and stir for 4 hours at room temperature , separated on a silica gel column, and the product was directly used in the next reaction. Last step product (1.0eq), H 2 (2.0eq), add ethanol...

example 2

[0022] In the general structural formula I series, n=1, R=N(CH 2 CH 3 ) 2 Prepared by the method 1.2.3 in the above-mentioned Example 1. The NMR data are as follows:

[0023] 1 H-NMR (300MHz, DMSO-d 6 )δ: 9.78 (1H, brs), 8.35 (1H, s), 7.07 (1H, brs), 7.03 (1H, d, J = 8.4Hz), 6.95 (1H, d, J = 8.4Hz), 6.61 ( 1H, s), 5.40 (1H, t, J=6.0Hz), 5.04 (1H, t, J=6.0Hz), 4.54 (2H, d, J=6.0Hz), 4.09 (1H, q, J=6.9 Hz), 4.00(2H, t, J=6.3Hz), 2.51(2H, t, J=6.9Hz), 2.44(4H, q, J=7.2Hz), 2.05(4H, m), 1.78(2H, m), 1.68 (3H, s), 1.62 (3H, s), 1.55 (3H, s), 1.32 (3H, d, J = 6.9 Hz), 0.92 (6H, t, J = 7.2 Hz).

example 3

[0025] In the general structural formula I series, n=1, R=N(CH 2 CH 2 ) 2 Prepared by the method 1.2.3 in the above-mentioned Example 1. The NMR data are as follows:

[0026] 1 H-NMR (300MHz, DMSO-d 6 )δ: 9.78 (1H, brs), 8.35 (1H, s), 7.07 (1H, brs), 7.04 (1H, d, J = 8.4Hz), 6.95 (1H, d, J = 8.4Hz), 6.62 ( 1H, s), 5.40 (1H, t, J=6.0Hz), 5.04 (1H, t, J=6.0Hz), 4.55 (2H, d, J=6.0Hz), 4.10 (1H, q, J=6.9 Hz), 4.00(2H, t, J=6.3Hz), 2.51(2H, t, J=7.2Hz), 2.41(4H, m), 2.05(4H, m), 1.86(2H, m), 1.68( 3H, s), 1.66 (4H, m), 1.62 (3H, s), 1.55 (3H, s), 1.32 (3H, d, J = 6.9 Hz).

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Abstract

The invention belongs to the field of medical technology, relating to a new diketone piperazidine-like derivative and application thereof, specifically relating to a new diketone piperazidine-like derivative capable of treating tumor diseases. The structural formula of the compound is shown in the figure I and the figure II; n can be 0, 1, 2; the base group R can be amino-group, ethylamino group, tri-amino, abnormal tri-amino, fourth amino, abnormal fourth amino, tertiary butyl amino, circular tri-amino, circular fifth-amino, hexamethylene amino, dimethyl amino, diethylin, tetralin pyrrolyl, hexahydropyridine group, 4-methyl hexahydropyridine group, morpholinyl, piperazine group, and nitrogen methyl piperazine group. The compound has stable and definite structure, and the anti-tumor activity experiments show that the compound has very strong antitumor activity and has the advantages of strong active activity, small dosage, and the like. The diketone piperazidine-like derivative can be made into preparation for treating tumor diseases.

Description

technical field [0001] The invention belongs to the technical field of medicine and relates to new diketopiperazine derivatives and applications thereof. It specifically relates to new diketopiperazine derivatives and their application in the preparation of antitumor drugs. Background technique [0002] Cancer is one of the major threats to modern human health. Although in recent decades, people have made great efforts to conquer cancer, but it is still far from the goal of conquering cancer. Cancer is still one of the important causes of human death . Antitumor active compound diketopiperazine derivatives are a class of natural products with diketopiperazine ring structure characteristics, and have shown good activity on HL-60 human leukemia cancer cells. [0003] In recent years, with the breakthrough and development of human genomics, molecular and cell biology, and new drug design technology, people have a deeper understanding and understanding of the pathology and mec...

Claims

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Application Information

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IPC IPC(8): C07D241/18A61K31/495A61K31/496A61P35/00
Inventor 裴月湖吴彪华会明
Owner SHENYANG PHARMA UNIVERSITY
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