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Acetamide derivative and application thereof in pharmacy

A technology of acetamide and derivatives, applied in the field of medicine, can solve the problems of listing, no drugs, and cancer cells initiating programmed death.

Active Publication Date: 2010-05-26
JIANGSU CAREFREE PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] At present, there are studies at home and abroad on caspase-3 causing cancer cells to initiate programmed death, but it is still in its infancy, and there is no real drug on the market.

Method used

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  • Acetamide derivative and application thereof in pharmacy
  • Acetamide derivative and application thereof in pharmacy
  • Acetamide derivative and application thereof in pharmacy

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Example 1.2-(4-benzyl-2-piperazinon-1-yl)-N-[(2-hydroxyl-3-allyl-phenyl)methyleneamino]acetamide (I 1 ) preparation and structure confirmation

[0037] (1). Synthesis of 4-benzyl-2-piperazinone

[0038] Add 5.1g of 2-piperazinone, 5.0g of benzyl chloride and 4.2g of sodium bicarbonate into 60ml of ethanol respectively, stir, heat to reflux for 5h, cool to room temperature, filter, concentrate the filtrate to obtain a solid, recrystallize from benzene to obtain 8.6g of white crystals (melting point 152-154°C).

[0039] (2). Synthesis of 2-(4-benzyl-2-piperazinon-1-yl)-ethyl acetate

[0040] Add 8.55g of 4-benzyl-2-piperazinone and an appropriate amount of sodium hydride into dry 100mL of acetone, stir, add 6.2g of ethyl bromoacetate dropwise, start heating and refluxing until the reaction of the raw materials is complete, cool, filter, After washing, the filtrate was concentrated to obtain an oil, and column chromatography (eluent: ethyl acetate / n-hexane=4 / 1) obtained...

Embodiment 2

[0047] Example 2.2-[4-(3-pyridyl-methyl)-2-piperazinon-1-yl]-N-[(2-hydroxyl-3-allyl-phenyl)methyleneamino ] Acetamide (I 2 ) preparation and structure confirmation

[0048] (1). Synthesis of 4-(3-pyridyl-methyl)-2-piperazinone

[0049] Add 5.1g 2-piperazinone, 5.0g 3-chloromethylpyridine and 4.2g sodium bicarbonate into 60ml of ethanol respectively, stir, heat to reflux for 5h, cool to room temperature, filter, concentrate the filtrate, column chromatography (eluent : chloroform / methanol=10 / 1), collect eluent, concentrate to obtain product.

[0050] The resulting product obtains the target product in the same manner as (2), (3), and (4) in Example 1.

[0051] 1 H-NMR (DMSO, -d 6 )δ8.75(s, 1H), 8.6(s, 1H), 8.15(s, 1H), 7.95(s, 1H), 7.8(s, 1H), 7.5(s, 1H), 7.2(s, 1H ), 6.8(s, H), 6.65(s, H), 6.25(s, H), 5.16(s, 1H), 4.91(ddd, 2H), 4.12(dd, 2H), 3.66(dd, 2H) , 3.37(s, 2H), 3.24(d, 2H), 3.16(d, 2H), 2.64(d, 2H).

[0052]

Embodiment 3

[0053] Example 3.2-(4-p-toluenesulfonyl-2-piperazinonyl-1-yl)-N-[(2-hydroxyl-3-allyl-phenyl)methyleneamino]acetamide (I 3 ) preparation and structure confirmation

[0054] (1). Synthesis of 4-p-toluenesulfonyl-2-piperazinone

[0055] Add 5.1g of 2-piperazinone, 7.6g of p-toluenesulfonyl chloride and 5.1g of triethylamine into 60ml of dichloromethane respectively, stir, heat to reflux for 5h until the reaction is complete, cool to room temperature, filter, concentrate the filtrate, and perform column chromatography (Eluent: chloroform / methanol=10 / 1), collect the eluent, and concentrate to obtain the product.

[0056] The resulting product obtains the target product in the same manner as (2), (3), and (4) in Example 1.

[0057] 1 H-NMR (DMSO-d 6 )δ8.15(s, 1H), 7.90(s, 1H), 7.81(s, 2H), 7.35(s, 1H), 7.23(s, 2H), 6.9(s, H), 6.63(s, H ), 6.2(s, H), 5.10(s, 1H), 4.91(ddd, 2H), 4.2(dd, 2H), 3.38(s, 2H), 3.28(d, 2H), 3.16(d, 2H) , 2.60(d, 2H), 2.32(d, 3H).

[0058]

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Abstract

The invention provides an acetamide derivative with the structural formula as follows: R represents -X-Ar, -X-COOH, -CO-Ar, -SO2-Ar, -X-Het., or -X-NR1R2, wherein X represents alkylene with 1-8 carbon atoms and the alkylene is not substituted or is substituted by straight chain hydrocarbon or branched hydrocarbon with 1-5 carbon atoms; and Ar represents phenyl, pyridyl, naphthyl, pyrimidyl and quinolyl. The derivative can cause apoptosis by acting on Caspase-3 zymogen in cancer cells and can be widely applied in cancer treatment.

Description

Technical field [0001] The present invention relates to a compound derivative and its preparation method and its application in pharmaceuticals, in particular to an acetamide derivative and its preparation method and its application in pharmaceuticals, and belongs to the field of medical technology. Background technique [0002] Apoptosis and cell proliferation are basic phenomena of life and are basic measures to maintain the dynamic balance of cell numbers in the body. In the embryonic development stage, apoptosis is used to remove excess cells and cells that have completed their mission, ensuring the normal development of the embryo; in the adult stage, apoptosis is used to remove aging and diseased cells, ensuring the health of the body. Like cell proliferation, apoptosis is a precise process regulated by genes. There are two main pathways of apoptosis, one is to activate the intracellular apoptotic enzyme caspase (caspase) through extracellular signals, and the other i...

Claims

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Application Information

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IPC IPC(8): C07D241/08C07D241/06C07D405/04A61K31/495A61K31/496A61P35/00
Inventor 秦引林刘现军
Owner JIANGSU CAREFREE PHARM CO LTD
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